Articles in JSON/article 8.json

{"lines":[{"page":1,"text":"materials","rect":[74.04940795898438,73.27265167236328,164.663183053868,56.33888244628906]},{"page":1,"text":"Article","rect":[35.3415412902832,112.58541870117188,63.184056418425658,105.19103240966797]},{"page":1,"text":"Photoinduced Phase Transitions of Imine-Based Liquid Crystal","rect":[35.699378967285159,136.04318237304688,551.4405945552328,118.39805603027344]},{"page":1,"text":"Dimers with Twist–Bend Nematic Phases","rect":[35.699378967285159,150.3917236328125,373.55795908145628,137.20713806152345]},{"page":1,"text":"Yuki Arakawa * and Yuto Arai","rect":[35.37153244018555,174.7465057373047,181.53954884110224,167.42173767089845]},{"page":1,"text":"Citation: Arakawa, Y.; Arai, Y.","rect":[35.699440002441409,498.3646240234375,127.66421917129623,492.24810791015627]},{"page":1,"text":"Photoinduced Phase Transitions of","rect":[35.70343780517578,509.3514709472656,139.43243534021929,504.1475524902344]},{"page":1,"text":"Imine-Based Liquid Crystal Dimers","rect":[35.70343780517578,523.0960083007813,141.99064608561214,516.0738525390625]},{"page":1,"text":"with Twist–Bend Nematic Phases.","rect":[35.41057586669922,533.17626953125,136.98568370987045,527.9862670898438]},{"page":1,"text":"Materials 2024, 17, 3278.","rect":[35.69944381713867,546.0300903320313,108.10979870010482,539.8508911132813]},{"page":1,"text":"https://","rect":[112.43154907226563,546.9078979492188,138.3690304670228,539.899658203125]},{"page":1,"text":"doi.org/10.3390/ma17133278","rect":[35.699440002441409,558.8341674804688,126.47016197540494,551.81201171875]},{"page":1,"text":"AcademicEditors: MarliFerreiraand","rect":[35.542510986328128,574.8861694335938,140.74235376036087,569.6961669921875]},{"page":1,"text":"Aloir Antonio Merlo","rect":[35.43156051635742,586.7985229492188,93.74732050263047,581.6085205078125]},{"page":1,"text":"Received: 30 May 2024","rect":[35.699440002441409,607.5097045898438,105.9488149295065,600.487548828125]},{"page":1,"text":"Revised: 26 June 2024","rect":[35.699440002441409,618.8448486328125,102.43564659454556,612.4009399414063]},{"page":1,"text":"Accepted: 27 June 2024","rect":[35.42756652832031,631.3215942382813,106.65978294708462,624.3133544921875]},{"page":1,"text":"Published: 3 July 2024","rect":[35.699440002441409,643.2478637695313,103.87855583526822,636.2257080078125]},{"page":1,"text":"Copyright:","rect":[35.699440002441409,689.7661743164063,70.65920845244261,682.9042358398438]},{"page":1,"text":"© 2024 by the authors.","rect":[76.23263549804688,689.8845825195313,153.084837114552,682.8624267578125]},{"page":1,"text":"Licensee","rect":[35.699440002441409,700.0,62.63914672739958,695.0]},{"page":1,"text":"MDPI,","rect":[66.42876434326172,700.0,87.12591377470824,695.0]},{"page":1,"text":"Basel,","rect":[90.91552734375,700.0,109.0815183279309,694.7757568359375]},{"page":1,"text":"Switzerland.","rect":[113.38304901123047,700.0,153.08517280791137,694.7757568359375]},{"page":1,"text":"This article is an open access article","rect":[35.48353958129883,713.6964111328125,151.86675445445037,706.6881713867188]},{"page":1,"text":"distributed","rect":[35.699440002441409,723.7905883789063,70.6094326672424,718.6005859375]},{"page":1,"text":"under","rect":[76.24764251708985,723.7905883789063,95.23127774841402,718.6005859375]},{"page":1,"text":"the","rect":[100.86949157714844,723.7905883789063,110.73103515513395,718.6005859375]},{"page":1,"text":"terms","rect":[116.36925506591797,723.7905883789063,134.1939826232333,719.33203125]},{"page":1,"text":"and","rect":[139.83218383789063,723.73486328125,151.86938902710569,718.6005859375]},{"page":1,"text":"conditions of the Creative Commons","rect":[35.699440002441409,735.7039794921875,151.8693976622958,730.5000610351563]},{"page":1,"text":"Attribution (CC BY) license (https://","rect":[35.42757034301758,749.4345703125,153.13324709438496,742.4263305664063]},{"page":1,"text":"creativecommons.org/licenses/by/","rect":[35.699440002441409,761.3609008789063,148.32147951625996,754.3387451171875]},{"page":1,"text":"4.0/).","rect":[35.699440002441409,772.8005981445313,52.700649530182939,766.2521362304688]},{"page":1,"text":"Department of Applied Chemistry and Life Science, Graduate School of Engineering, Toyohashi University of","rect":[166.31678771972657,206.29627990722657,552.1299247378838,198.25498962402345]},{"page":1,"text":"Technology, 1-1 Hibarigaoka, Tempaku-cho, Toyohashi 441-8580, Aichi, Japan; arai.yuto.du@tut.jp","rect":[166.0688934326172,217.0448760986328,510.16976751474348,209.01950073242188]},{"page":1,"text":"* Correspondence: arakawa@tut.jp","rect":[165.6071014404297,227.79249572753907,290.8789044776341,219.76712036132813]},{"page":1,"text":"Abstract: Photoisomerizable molecules in liquid crystals (LCs) allow for photoinduced phase transi-","rect":[165.96693420410157,250.59036254882813,560.5044839249455,241.5438690185547]},{"page":1,"text":"tions, facilitating applications in a wide variety of photoresponsive materials. In contrast to the widely","rect":[166.31678771972657,263.5486145019531,559.3646698860404,254.5021209716797]},{"page":1,"text":"investigated azobenzene structure, research on the photoinduced phase-transition behavior of imine-","rect":[166.31678771972657,276.5058898925781,560.5073418167242,267.45941162109377]},{"page":1,"text":"based LCs is considerably limited. We herein report the thermal and photoinduced phase-transition","rect":[166.31678771972657,289.4642639160156,559.0136751860399,280.4356994628906]},{"page":1,"text":"behaviors of photoisomerizable imine-based LC dimers with twist–bend nematic (NTB) phases. We","rect":[166.31678771972657,302.403564453125,559.0155095897508,293.375]},{"page":1,"text":"synthesize two homologous series of ester- and thioether-linked N-(4-cyanobenzylidene)aniline-","rect":[166.31678771972657,315.3787536621094,560.5052968283538,306.332275390625]},{"page":1,"text":"based bent-shaped LC dimers with an even number of carbon atoms (n = 2, 4, 6, 8, and 10) in the","rect":[166.31678771972657,328.319091796875,559.0139651681571,319.29052734375]},{"page":1,"text":"central alkylene spacers, namely, CBCOOnSBA(CN) and CBOCOnSBA(CN), possessing oppositely","rect":[166.31678771972657,341.2943420410156,559.3688619101293,332.2657775878906]},{"page":1,"text":"directed ester linkages, C=OO and OC=O, respectively. Their thermal phase-transition behavior","rect":[166.31678771972657,354.2516174316406,559.1994493965623,345.2230529785156]},{"page":1,"text":"is examined using polarizing optical microscopy and differential scanning calorimetry. All dimers","rect":[166.31678771972657,367.2099304199219,559.0201980931568,358.1634521484375]},{"page":1,"text":"form a monotropic NTB phase below the temperature of the conventional nematic (N) phase upon","rect":[166.31678771972657,380.1492919921875,559.0138364397785,371.1207275390625]},{"page":1,"text":"cooling. Remarkably, the NTB phases of CBCOOnSBA(CN) (n = 2, 4, 6, and 8) and CBOCOnSBA(CN)","rect":[166.31678771972657,393.1255187988281,559.9125542190679,384.07904052734377]},{"page":1,"text":"(n = 6 and 8) supercool to room temperature and vitrify without crystallization. In addition, the","rect":[166.0209197998047,406.082763671875,559.0139041330009,397.0362854003906]},{"page":1,"text":"phase-transition temperatures and entropy changes of CBCOOnSBA(CN) are lower than those of","rect":[166.0479278564453,419.0400695800781,559.0187245627288,409.99359130859377]},{"page":1,"text":"CBOCOnSBA(CN) at the same n. Under UV light irradiation, the NTB and N phases transition to the","rect":[166.31678771972657,431.9983825683594,559.0198414052666,422.9698181152344]},{"page":1,"text":"N and isotropic phases, respectively, and reversibly return to their initial LC phases when the UV","rect":[166.31678771972657,444.95562744140627,559.336725915896,435.92706298828127]},{"page":1,"text":"light is turned off.","rect":[166.31678771972657,457.9129333496094,237.5755824823124,448.866455078125]},{"page":1,"text":"Keywords: liquid crystal dimer; twist–bend nematic phase; thioether; ester direction; imine bond;","rect":[166.31678771972657,482.8135986328125,560.1367511570904,473.7850341796875]},{"page":1,"text":"benzylideneaniline; photoinduced phase transition","rect":[166.31678771972657,495.7708740234375,367.8776459602295,486.7423095703125]},{"page":1,"text":"1. Introduction","rect":[166.31678771972657,543.4513549804688,234.39951176968783,536.1266479492188]},{"page":1,"text":"Photoisomerizable building blocks coupled with liquid crystals (LCs) have attracted","rect":[187.56594848632813,561.6240844726563,559.0142840157345,551.5924072265625]},{"page":1,"text":"considerable attention for a variety of applications such as optical storage [1–4], photo-","rect":[166.31678771972657,574.163818359375,560.6682775032049,564.1122436523438]},{"page":1,"text":"mobile materials [5–8], photoalignments [9,10], and adhesion [11,12]. In particular, the","rect":[166.31678771972657,586.7035522460938,559.0116326181025,576.671875]},{"page":1,"text":"azobenzene (Ph–N=N–Ph) structure is well-known for its mesogenic and reversible trans–","rect":[166.31678771972657,599.2432861328125,560.5102922564145,589.1917114257813]},{"page":1,"text":"cis isomerization abilities. The trans isomer, stable under ambient temperature, transforms","rect":[166.31678771972657,611.7631225585938,559.0181791730894,601.7314453125]},{"page":1,"text":"into the cis isomer upon UV light irradiation [13], and the generated cis isomer reverts to","rect":[166.31678771972657,624.32275390625,559.0209230135591,614.2910766601563]},{"page":1,"text":"the initial trans isomer upon irradiation with visible light or by heating. This trans-to-cis","rect":[166.31678771972657,636.8624877929688,559.0164352829879,626.830810546875]},{"page":1,"text":"isomerization disorders the molecular arrangements in LC phases. Consequently, LC","rect":[166.31678771972657,649.4021606445313,559.0121426155652,639.3704833984375]},{"page":1,"text":"phases, such as nematic (N) [1,14], blue (BP) [15], layered smectic (Sm) [16], and columnar","rect":[166.01792907714845,661.94189453125,559.2149438516877,651.9102172851563]},{"page":1,"text":"phases, [17] in trans azobenzenes transition to isotropic (Iso) phases, which reversibly","rect":[166.01792907714845,674.4816284179688,559.403290544308,664.449951171875]},{"page":1,"text":"return to the initial LC phases. However, some LC phases rearrange into other LC and","rect":[166.31678771972657,687.0213623046875,559.0121041718433,676.9896850585938]},{"page":1,"text":"chiral Iso phases [18–21]. Even solid crystals of certain azobenzenes can liquefy to the Iso","rect":[166.31678771972657,699.5610961914063,559.0136812655567,689.509521484375]},{"page":1,"text":"phase [11,22]. These phenomena are known as the photoinduced (or light-induced) phase","rect":[166.01792907714845,712.100830078125,559.0112392910839,702.0691528320313]},{"page":1,"text":"transitions for LCs. Additionally, photoisomerization of the azobenzene structures follows","rect":[166.31678771972657,724.6405639648438,559.0135694010674,714.5889892578125]},{"page":1,"text":"the Weigert effect. Upon irradiation with linearly polarized light, the molecular anisotropic","rect":[166.31678771972657,737.1802978515625,559.0117497598548,727.1287231445313]},{"page":1,"text":"polarization direction (long axis) of azobenzene becomes normal to that of the exposed","rect":[166.01792907714845,749.7200317382813,559.0179635468433,739.66845703125]},{"page":1,"text":"light, thus inducing a change in the shape and surface of LC materials for the applications","rect":[166.31678771972657,762.259765625,559.0192384457935,752.2081909179688]},{"page":1,"text":"mentioned above.","rect":[166.31678771972657,772.1810913085938,245.2039116850899,764.7667846679688]},{"page":1,"text":"Materials 2024, 17, 3278. https://doi.org/10.3390/ma17133278","rect":[35.699378967285159,822.0076293945313,254.30583442073863,813.926513671875]},{"page":1,"text":"https://www.mdpi.com/journal/materials","rect":[404.9346008300781,822.0076293945313,559.0128876278488,813.9822998046875]},{"page":2,"text":"Materials 2024, 17, 3278","rect":[35.699440002441409,57.948081970214847,116.46322882991832,50.886077880859378]},{"page":2,"text":"2 of 14","rect":[536.0813598632813,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":2,"text":"Similarly, the rigid and anisotropic imine-based N-benzylideneaniline (Ph–CH=N–Ph)","rect":[187.56600952148438,99.5560531616211,560.0138266331892,89.52436828613281]},{"page":2,"text":"structure is a commonly used building block for LC molecules [23–43]. Similar to that of","rect":[166.3168487548828,112.09578704833985,559.0180702078397,102.04420471191406]},{"page":2,"text":"azobenzene, the –CH=N– imine bond in the N-benzylideneaniline structure undergoes","rect":[166.3168487548828,124.63545989990235,559.0120719202547,114.60377502441406]},{"page":2,"text":"reversible trans–cis isomerization upon irradiation with UV light [44–46]. The trans-to-cis","rect":[166.3168487548828,137.17532348632813,559.0164560252673,127.14363098144531]},{"page":2,"text":"isomerization of the imine bond requires more energy (~50–60 kcal mol−1) [46–48] than","rect":[166.3168487548828,149.71505737304688,559.019610084782,138.0471954345703]},{"page":2,"text":"that of azobenzene (<~50 kcal mol−1) [7]. As a notable difference, the imine bond shows","rect":[166.3168487548828,161.57798767089845,559.0178984054144,150.58595275878907]},{"page":2,"text":"remarkably faster thermal back-relaxation from cis-to-trans forms than the azo bond. The","rect":[166.3168487548828,174.79446411132813,559.0116352498483,164.7428741455078]},{"page":2,"text":"energy barrier for the thermal back-relaxation of imine bonds (~16 kcal mol−1) is lower","rect":[166.3168487548828,187.33419799804688,559.210862012881,175.6653594970703]},{"page":2,"text":"than those of azobenzene (~23 kcal mol−1) and structurally similar stilbene Ph–CH=CH–Ph","rect":[166.3168487548828,199.87393188476563,559.013557460764,188.2051544189453]},{"page":2,"text":"(42 kcal mol−1), resulting in a short half-life of the cis isomer of the imine at ambient","rect":[165.98800659179688,212.41366577148438,559.0176487109078,200.74488830566407]},{"page":2,"text":"temperature [45,46]. Accordingly, the cis state of imine molecules can be detected by","rect":[166.3168487548828,224.95339965820313,559.4039619310267,214.9018096923828]},{"page":2,"text":"UV–visible spectroscopy only at low temperatures below –70 ◦C and not at ambient temper-","rect":[166.3168487548828,237.49313354492188,560.6729053374692,227.46144104003907]},{"page":2,"text":"atures[45,46]. AnadvantageofN-benzylideneanilineoverazobenzeneis itstransparency in","rect":[166.3168487548828,250.03280639648438,559.018928554514,239.98121643066407]},{"page":2,"text":"the visible region, which is crucial for practical applications. However, the current research","rect":[166.3168487548828,262.5726623535156,559.0114762030444,252.5210723876953]},{"page":2,"text":"on the photoisomerization behaviors of N-benzylideneaniline-based LCs is considerably","rect":[166.3168487548828,275.1122741699219,559.4088270896896,265.0606689453125]},{"page":2,"text":"limited [49–54]. In the presence of N-benzylideneaniline-based molecules, the LC phases","rect":[166.3168487548828,287.6520690917969,559.0153321964261,277.6004638671875]},{"page":2,"text":"reversibly transition to Iso phases upon UV light irradiation [53,54]. Kawatsuki and Kondo","rect":[166.3168487548828,300.1908264160156,559.0125206479929,290.1591491699219]},{"page":2,"text":"et al. investigated the photoisomerization of N-benzylideneaniline-based LC polymers","rect":[166.3168487548828,312.7304992675781,559.0142691858797,302.67889404296877]},{"page":2,"text":"for photoreorientation and adhesion applications [49–53]. Hu and Yu recently reported","rect":[166.3168487548828,325.2702331542969,559.015216964812,315.2186279296875]},{"page":2,"text":"a solid-to-liquid phase transition of N-benzylideneaniline with asymmetric alkyl chain","rect":[166.3168487548828,337.8099670410156,559.0202204363445,327.75836181640627]},{"page":2,"text":"substitution [54]. In addition to the photoisomerizability, Terentjev et al. demonstrated","rect":[166.3168487548828,350.3497009277344,559.015705246062,340.3180236816406]},{"page":2,"text":"the applicability of the bond exchangeable ability of N-benzylideneaniline embedded in","rect":[166.3168487548828,362.8894348144531,559.0133870121937,352.83782958984377]},{"page":2,"text":"LC elastomers [55]. Therefore, the use of N-benzylideneaniline for LCs has been continu-","rect":[166.3168487548828,375.4291687011719,560.6683407911164,365.3775634765625]},{"page":2,"text":"ously increasing.","rect":[166.3168487548828,387.9689025878906,240.46398248587117,377.9372253417969]},{"page":2,"text":"Over the last decade, the helical twist–bend nematic (NTB) phase for bent molecules","rect":[187.56600952148438,400.48870849609377,559.0183229190824,390.4570007324219]},{"page":2,"text":"has gained widespread interest in LC science [56–58]. The NTB phase exhibits heliconical","rect":[166.3168487548828,413.04833984375,559.0128707478943,403.01666259765627]},{"page":2,"text":"structures with pitches in the range of several to tens of nanometers, generated by the","rect":[166.3168487548828,425.58807373046877,559.0123040048212,415.5364685058594]},{"page":2,"text":"precession of bent molecules [59–61]. The heliconical structures of the NTB phase form","rect":[166.0179901123047,438.10791015625,559.0142262785573,428.0762023925781]},{"page":2,"text":"pseudo-layers, making the physical properties of this phase more similar to those of layered","rect":[166.0179901123047,450.66754150390627,559.0154963901274,440.6159362792969]},{"page":2,"text":"Sm phases than to the conventional N phase [62–65]. The majority of the NTB phase is","rect":[166.3168487548828,463.2072448730469,559.0158560999422,453.1556396484375]},{"page":2,"text":"observed for bent LC dimers composed of two mesogenic arms linked via a central spacer","rect":[166.3168487548828,475.7469787597656,559.2176359808626,465.69537353515627]},{"page":2,"text":"withanoddnumberoftotalatomsalongthespacer[66–71]. Themolecularbiaxialitiesofthe","rect":[165.89805603027345,488.2867126464844,559.0166996261123,478.235107421875]},{"page":2,"text":"bent dimers can be associated with NTB phase induction [72]. Twist–bend nematogenic bent","rect":[166.3168487548828,500.82647705078127,559.013284993124,490.7947998046875]},{"page":2,"text":"dimers are also useful for photonic applications with wavelength or color tunability [73,74].","rect":[166.3168487548828,513.3661499023438,560.7589192455897,503.3145751953125]},{"page":2,"text":"The photoinduced phase-transition behavior of the NTB phase has been evaluated for","rect":[166.00799560546876,525.885986328125,559.2162941417872,515.8543090820313]},{"page":2,"text":"azobenzene-based LC dimers [75,76]. Under moderate UV irradiation, the NTB phase","rect":[166.3168487548828,538.4257202148438,559.0163323251337,528.4139404296875]},{"page":2,"text":"transitions to the conventional N phase, exhibiting reversibility when the light is switched","rect":[166.3168487548828,550.9852905273438,559.0194160701002,540.95361328125]},{"page":2,"text":"on and off [75]. Owing to the Weigert effect, the molecular and helical axes of the NTB phase","rect":[166.3168487548828,563.5250854492188,559.0166996261123,553.4735107421875]},{"page":2,"text":"can be oriented perpendicular to the polarization direction of the polarized linear light [76].","rect":[166.3168487548828,576.0648193359375,560.7589192455897,566.0132446289063]},{"page":2,"text":"However, to the best of our knowledge, the photoinduced phase-transition behaviors of","rect":[166.3168487548828,588.6045532226563,559.0120885383611,578.552978515625]},{"page":2,"text":"the LC phases for imine-based LC dimers have not been reported to date.","rect":[166.3168487548828,601.1243896484375,488.40770807180868,591.0927124023438]},{"page":2,"text":"We herein report the synthesis and thermal and photoinduced phase-transition be-","rect":[187.56600952148438,613.6840209960938,560.6682164680486,603.65234375]},{"page":2,"text":"haviors for the N and NTB phases of N-benzylideneaniline-based LC dimers. We syn-","rect":[166.3168487548828,626.2236938476563,560.6732213508611,616.172119140625]},{"page":2,"text":"thesized two new homologous series of oppositely directed ester- and thioether-linked","rect":[166.3168487548828,638.762451171875,559.0122262421558,628.7108764648438]},{"page":2,"text":"N-(4-cyanobenzylidene)aniline- and 4-cyanobiphenyl-based dimers [CBCOOnSBA(CN)","rect":[166.3168487548828,651.3021850585938,560.0120885383611,641.2705078125]},{"page":2,"text":"and CBOCOnSBA(CN)] with even-numbered alkylene spacers (n = 2, 4, 6, 8, and 10)","rect":[166.3168487548828,663.8418579101563,560.0101354133611,653.8101806640625]},{"page":2,"text":"and total odd number of atoms to obtain bent molecular shapes (Figure 1c). The series","rect":[166.3168487548828,676.3816528320313,559.0121939905672,666.330078125]},{"page":2,"text":"differs in the ester linkage directions, viz., C=OO or OC=O for CBCOOnSBA(CN) and","rect":[166.3168487548828,688.92138671875,559.0208932343433,678.8698120117188]},{"page":2,"text":"CBOCOnSBA(CN), respectively. We previously reported two homologous series of oppo-","rect":[166.3168487548828,701.4611206054688,560.6703359194033,691.4095458984375]},{"page":2,"text":"sitely directed ester- and thioether-linked cyanobiphenyl LC dimers, CBCOOnSCB and","rect":[166.3168487548828,714.0008544921875,559.0114938202808,703.9691772460938]},{"page":2,"text":"CBOCOnSCB, as given in Figure 1a [33,77]. These dimers exhibit the NTB phases, which can","rect":[166.3168487548828,726.5405883789063,559.0170974998265,716.5089111328125]},{"page":2,"text":"be stably cooled to the ambient temperature and vitrifed; however, their phase-transition","rect":[166.3168487548828,739.0802612304688,559.0149690270997,729.0286865234375]},{"page":2,"text":"behaviors, helical pitches, and viscoelastic properties differ substantially owing to the ester","rect":[166.3168487548828,751.6199951171875,559.2154725639765,741.5684204101563]},{"page":2,"text":"directions [33,77–79]. Furthermore, thioether-linked N-(4-cyanobenzylidene)aniline- and","rect":[166.3168487548828,764.1597290039063,559.0154509423478,754.1280517578125]},{"page":3,"text":"Materials 2024, 17, 3278","rect":[35.699440002441409,57.948081970214847,116.46322882991832,50.886077880859378]},{"page":3,"text":"3 of 14","rect":[536.0813598632813,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":3,"text":"4-cyanobiphenyl-based bent dimers, CBSnSBA(CN) (Figure 1b) exhibit stable and vitrifable","rect":[166.3168487548828,99.5560531616211,559.0168216964248,89.50447082519531]},{"page":3,"text":"NTB phases [34]. In this context, we designed N-(4-cyanobenzylidene)aniline-containing LC","rect":[166.3168487548828,112.09578704833985,559.0203228125236,102.06410217285156]},{"page":3,"text":"dimers with thioether and oppositely directed ester linkages for new twist–bend nemato-","rect":[166.3168487548828,124.63545989990235,560.6647001905321,114.58387756347656]},{"page":3,"text":"gens to elucidate their thermal and photoinduced phase-transition behaviors. The thermal","rect":[166.3168487548828,137.17532348632813,559.0137240471783,127.14363098144531]},{"page":3,"text":"phase-transition behavior was evaluated using polarizing optical microscopy (POM) and","rect":[166.0179901123047,149.71505737304688,559.0130022774532,139.68336486816407]},{"page":3,"text":"differential scanning calorimetry (DSC). Additionally, POM was used to analyze the pho-","rect":[166.3168487548828,162.25473022460938,560.6647001905321,152.20314025878907]},{"page":3,"text":"toinduced phase transitions via UV irradiation of the LC phases.","rect":[166.3168487548828,174.77455139160157,449.58153619680868,164.7428741455078]},{"page":3,"text":"Figure 1. Molecular structures of (a) CBCOOnSCB, CBOCOnSCB, [33,77] (b) CBSnSBA(CN) [34] from","rect":[166.3168487548828,418.305419921875,559.016434209544,409.41119384765627]},{"page":3,"text":"our previous study, and (c) CBCOOnSBA(CN) and CBOCOnSBA(CN) in the present study.","rect":[166.3168487548828,431.26611328125,525.4851283807499,422.237548828125]},{"page":3,"text":"2. Materials and Methods","rect":[166.31686401367188,449.1630554199219,282.51655828553217,441.83831787109377]},{"page":3,"text":"All chemicals were commercially available and used as received. The synthetic scheme","rect":[187.56600952148438,467.3359069824219,559.0160282393936,457.3042297363281]},{"page":3,"text":"for the two homologous series is outlined in Scheme 1. The molecular structures were","rect":[166.3168487548828,479.8756103515625,559.0121208993525,469.8240051269531]},{"page":3,"text":"characterized by 1H and 13C nuclear magnetic resonance (NMR) spectroscopies using","rect":[166.3168487548828,492.41534423828127,559.0137031419642,480.74658203125]},{"page":3,"text":"JEOL JNM-ECS400 (400 and 100 MHz for 1H and 13C NMR, respectively) or JEOL JNM-","rect":[166.1469268798828,504.9550476074219,560.6683995735174,493.28631591796877]},{"page":3,"text":"ECX500 (500 and 125 MHz for 1H and 13C NMR, respectively) spectrometers. The synthetic","rect":[166.3168487548828,517.4948120117188,559.0117497598548,505.82598876953127]},{"page":3,"text":"procedures and characterization data are provided in Supporting Information. The thermal","rect":[166.0179901123047,530.0335083007813,559.0154152049914,519.98193359375]},{"page":3,"text":"phase transitions and phase identifcation were evaluated by POM using an Olympus BX50","rect":[166.0179901123047,542.5732421875,559.0153970849293,532.5216674804688]},{"page":3,"text":"optical microscope equipped with a Linkam temperature controller (LK-600PM). For planar","rect":[166.3168487548828,555.0930786132813,559.216672974438,545.081298828125]},{"page":3,"text":"and uniaxial alignment observation, polyimide surface cells with thicknesses of 1 and 7 µm","rect":[166.3168487548828,567.6526489257813,559.0157210371415,557.60107421875]},{"page":3,"text":"were obtained from EHC Co., Ltd. (Hachioji-shi, Japan). The phase-transition temperatures","rect":[165.89805603027345,580.1924438476563,559.0126182514576,570.140869140625]},{"page":3,"text":"and associated enthalpy changes were determined using a Shimadzu DSC-60 Plus at a","rect":[166.3168487548828,592.732177734375,559.0121029793687,582.7005004882813]},{"page":3,"text":"rate of 10 ◦C min−1 under a nitrogen gas fow rate of 50 mL min−1 and liquid nitrogen","rect":[166.3168487548828,605.2719116210938,559.0185724871258,593.6041259765625]},{"page":3,"text":"(Liq. N2) was added for cooling. Indium was used for calibration. The photoinduced","rect":[165.98800659179688,617.8116455078125,559.0192452851245,607.7600708007813]},{"page":3,"text":"phase-transition behavior was observed using POM upon UV light irradiation. The 365-nm","rect":[166.0179901123047,630.351318359375,559.0154768965165,620.3196411132813]},{"page":3,"text":"UV light from the outer light source (Asahi Spectra LAX-C100) was refected by a dichroic","rect":[166.3168487548828,642.8910522460938,559.0197883814159,632.8394775390625]},{"page":3,"text":"half mirror inserted in an Olympus BX53M optical microscope, which was exposed to","rect":[166.3168487548828,655.4307861328125,559.0122293929237,645.3792114257813]},{"page":3,"text":"the LC samples in the non-treated glass cells with two pieces of commercial glass ona","rect":[166.3168487548828,667.9705200195313,559.0121029793687,657.9189453125]},{"page":3,"text":"Mettler Toledo HS82 hot-stage system. The UV light intensity (approximately 3 mW cm−2)","rect":[166.3168487548828,680.51025390625,560.0123202078505,668.8803100585938]},{"page":3,"text":"was monitored at each sample height using an Ushio UIT-201 digital UV intensity meter","rect":[165.89805603027345,693.0499877929688,559.218504572012,683.018310546875]},{"page":3,"text":"equipped with an Ushio photodetector UVD-365PD. The UV–visible absorption spectra for","rect":[166.3168487548828,705.56982421875,559.2171270954951,695.5381469726563]},{"page":3,"text":"both homologous series with n = 6 were recorded in tetrahydrofuran (THF) using a JASCO","rect":[166.3168487548828,718.1294555664063,559.0120296052521,708.077880859375]},{"page":3,"text":"V-630 UV–visible spectrophotometer.","rect":[165.95802307128907,730.6492919921875,328.6415337554024,720.6375122070313]},{"page":4,"text":"Materials 2024, 17, 3278","rect":[35.699440002441409,57.948081970214847,116.46322882991832,50.886077880859378]},{"page":4,"text":"4 of 14","rect":[536.0813598632813,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":4,"text":"Scheme 1. Synthesis of CBCOOnSBA(CN) and CBOCOnSBA(CN), where n = 2, 4, 6, 8, and 10.","rect":[166.3168487548828,593.9549560546875,538.5686855096561,584.908447265625]},{"page":4,"text":"3. Results and Discussion","rect":[166.31683349609376,611.8519287109375,283.0442871603128,604.5272216796875]},{"page":4,"text":"3.1. Thermal Phase Transitions","rect":[166.31683349609376,625.2279663085938,291.6678744726249,617.8335571289063]},{"page":4,"text":"The melting temperatures (Tm) upon heating, Iso–N phase transition (TIN), N–NTB","rect":[187.56600952148438,643.4605102539063,558.5185728911787,633.4288330078125]},{"page":4,"text":"phase-transition (TNNTB), glass transition (Tg), and crystallization (TCr) temperatures upon","rect":[166.0179901123047,656.819091796875,559.020934138914,645.967529296875]},{"page":4,"text":"cooling, along with their associated enthalpy changes (∆H) for CBCOOnSBA(CN) are listed","rect":[166.3168487548828,668.5389404296875,559.0134211948149,658.4873657226563]},{"page":4,"text":"in Table 1. Upon heating, the shorter spacer CBCOOnSBA(CN) homologs (n = 2, 4, and 6)","rect":[166.3168487548828,681.0786743164063,560.0070058412783,671.0469970703125]},{"page":4,"text":"did not exhibit LC phases, whereas longer spacers (n = 8 and 10) formed the conventional","rect":[166.3168487548828,693.618408203125,559.0174651908894,683.5668334960938]},{"page":4,"text":"N phase. All the CBCOOnSBA(CN) homologs exhibited NTB and N phases upon cooling.","rect":[166.3168487548828,706.1581420898438,560.7573747978596,696.12646484375]},{"page":4,"text":"The NTB phase was identifed by blocky (Figure 2a), striped (Figure 2b), focal-conic-like,","rect":[166.00799560546876,718.6978759765625,560.2589506596062,708.6463012695313]},{"page":4,"text":"or rope-like (Figure 2c) textures in the non-treated glass cells as shown for n = 6, 8, and","rect":[166.3168487548828,731.2376098632813,559.0174752655933,721.18603515625]},{"page":4,"text":"10, respectively. Specifcally, blocky textures were often observed beneath the N–NTB","rect":[165.81808471679688,743.77734375,558.5185728911787,733.7257690429688]},{"page":4,"text":"phase transition, as shown in Figure 2a. Shearing the cells led to striped textures along the","rect":[166.0179901123047,756.3170776367188,559.0154569980939,746.285400390625]},{"page":5,"text":"Materials 2024, 17, 3278","rect":[35.699440002441409,57.948081970214847,116.46322882991832,50.886077880859378]},{"page":5,"text":"5 of 14","rect":[536.0813598632813,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":5,"text":"shear direction, as shown in Figure 2b. This behavior is attributed to the Helfrich–Hurault","rect":[166.3168487548828,99.5560531616211,559.0194034660539,89.50447082519531]},{"page":5,"text":"mechanism of the pseudo-layered NTB phase [63,80].","rect":[166.3168487548828,112.09578704833985,398.2087639800118,102.04420471191406]},{"page":5,"text":"Table 1. Values of Tm upon heating, TIN, TNNTB, Tg, and TCr upon cooling at a rate of 10 ◦C min–1","rect":[166.02098083496095,137.3072509765625,558.8665090213034,125.91291809082031]},{"page":5,"text":"and their associated ∆H for CBCOOnSBA(CN).","rect":[166.31683349609376,148.72439575195313,353.2942714471561,140.28697204589845]},{"page":5,"text":"Figure 2. Optical textures observed in the NTB phases in a non-treated glass cell upon cooling","rect":[166.3168487548828,356.9217834472656,559.0120491241504,347.8932189941406]},{"page":5,"text":"CBCOOnSBA(CN): (a) blocky texture for n = 6, (b) striped texture for n = 8, and (c) rope-like and","rect":[166.3168487548828,369.7302551269531,559.0138543494134,360.68377685546877]},{"page":5,"text":"focal-conic-like textures for n = 10.","rect":[166.3168487548828,380.18304443359377,302.27199361512489,373.4922180175781]},{"page":5,"text":"The optical texture of the NTB phase of CBCOO2SBA(CN) was not as regular in","rect":[187.56600952148438,405.1726989746094,559.0194880144695,395.12109375]},{"page":5,"text":"the non-treated glass cells, as shown in Figure 3a. POM using uniaxially rubbed planar","rect":[166.3168487548828,417.71240234375,559.215256544131,407.68072509765627]},{"page":5,"text":"alignment cells with 1- and 7-µm thicknesses show lines or thin stripes growing along the","rect":[166.3168487548828,430.25213623046877,559.0169155606152,420.220458984375]},{"page":5,"text":"rubbing direction, as shown in Figure 3b,c, respectively. The stripes for a 7-µm-thick cell","rect":[166.3168487548828,442.7918701171875,559.0210408830756,432.7402648925781]},{"page":5,"text":"were wider and clearer than those for a 1-µm-thick one, which could be attributed to the","rect":[165.89805603027345,454.4956359863281,559.0119525851351,445.2799987792969]},{"page":5,"text":"Helfrich–Hurault-like instability of the pseudo-layer nature of the NTB phase [80]. The","rect":[166.3168487548828,467.871337890625,559.0149895516962,457.8197326660156]},{"page":5,"text":"stripes of CBCOO2SBA(CN) were relatively thinner and more ambiguous than those of","rect":[166.3168487548828,480.41107177734377,559.0122106086736,470.3594665527344]},{"page":5,"text":"typical stripes, which could be attributed to its high viscoelastic properties, as observed","rect":[166.3168487548828,492.9508056640625,559.012287277312,482.91912841796877]},{"page":5,"text":"for the structurally similar cyanobiphenyl dimer CBCOO4SCB, exhibiting similar textural","rect":[166.3168487548828,505.4905090332031,559.0194183158894,495.43890380859377]},{"page":5,"text":"behaviors [79].","rect":[166.3168487548828,517.0449829101563,231.05367364798054,507.9985656738281]},{"page":5,"text":"Figure 3. Optical textures of the NTB phase of CBCOO2SBA(CN) in (a) non-treated and uniaxially","rect":[166.3168487548828,650.3392944335938,559.3663798402041,641.2927856445313]},{"page":5,"text":"rubbed planar alignment glasses with cell thicknesses of (b) 1 and (c) 7 µm.","rect":[166.3168487548828,663.1477661132813,463.4259547967655,654.1012573242188]},{"page":5,"text":"The N–NTB phase-transition peaks of all the CBCOOnSBA(CN) dimers were detected","rect":[187.56600952148438,685.7617797851563,559.0113561625917,675.7301025390625]},{"page":5,"text":"by DSC, as shown in Figure 4. The shapes of the N–NTB phase-transition peaks suggest","rect":[166.3168487548828,698.3214111328125,559.018930449189,688.2698364257813]},{"page":5,"text":"that they are frst-order for shorter spacer CBCOOnSBA(CN) dimers (n < 8), which could","rect":[166.3168487548828,710.8611450195313,559.0121899267698,700.8095703125]},{"page":5,"text":"be attributed to the strong molecular biaxiality (molecular bend) of these dimers owing to","rect":[166.3168487548828,723.40087890625,559.0160782032663,713.3493041992188]},{"page":5,"text":"the small bond angle of the C–C(=O)–O ester linkage and the shorter spacer, as reported","rect":[166.3168487548828,735.9406127929688,559.011733606706,725.8890380859375]},{"page":5,"text":"previously [33,77–79]. The rigidity of the C–C(=O)–O ester linkage may also help to","rect":[166.0179901123047,748.4803466796875,559.0162577132362,738.4287719726563]},{"page":5,"text":"enhance their molecular biaxiality for the shorter spacer in terms of narrower plausible","rect":[166.3168487548828,761.0200805664063,559.0121208993525,750.968505859375]},{"page":5,"text":"conformation distributions.","rect":[166.3168487548828,770.9424438476563,287.17687311087118,763.5082397460938]},{"page":6,"text":"Materials 2024, 17,","rect":[35.699440002441409,57.948081970214847,98.53881961515447,50.886077880859378]},{"page":6,"text":"n","rect":[45.24501419067383,529.437255859375,49.120649370800688,526.0585327148438]},{"page":6,"text":"2","rect":[45.43992233276367,545.7843017578125,48.925205768129547,540.9705200195313]},{"page":6,"text":"4","rect":[45.43988800048828,552.8139038085938,48.92517143585415,547.9652709960938]},{"page":6,"text":"6","rect":[45.43988800048828,559.9299926757813,48.92517143585415,554.9977416992188]},{"page":6,"text":"8","rect":[45.439918518066409,566.8966674804688,48.92520195343228,561.9644165039063]},{"page":6,"text":"10","rect":[43.69774627685547,573.8632202148438,50.66831261017056,568.8961181640625]},{"page":6,"text":"Tm (◦C)","rect":[65.35368347167969,530.7822875976563,89.60978824549274,524.690673828125]},{"page":6,"text":"3278","rect":[100.5304183959961,56.87325668334961,116.46322882991832,51.23638916015625]},{"page":6,"text":"∆H","rect":[116.67387390136719,526.0343017578125,126.88275678714806,521.2413940429688]},{"page":6,"text":"(kJ mol–1)","rect":[106.28870391845703,535.4526977539063,137.5144971077974,528.1126098632813]},{"page":6,"text":"36.59","rect":[114.05818176269531,545.9027709960938,129.7419515261862,540.9705200195313]},{"page":6,"text":"43.66","rect":[114.05815124511719,552.932373046875,129.74192100860808,547.9652709960938]},{"page":6,"text":"38.28","rect":[114.05815124511719,559.9299926757813,129.74192100860808,554.9977416992188]},{"page":6,"text":"40.47","rect":[114.05818176269531,566.8966674804688,129.7419515261862,561.9295654296875]},{"page":6,"text":"43.44","rect":[114.05864715576172,573.8632202148438,129.7424169192526,568.8961181640625]},{"page":6,"text":"6 of 14","rect":[536.0813598632813,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":6,"text":"Figure 4. DSC curves of CBCOOnSBA(CN) upon cooling at a rate of 10 ◦C min−1.","rect":[166.3168487548828,310.4769592285156,489.9493007440311,299.8648986816406]},{"page":6,"text":"The phase-transition results for CBOCOnSBA(CN) are listed in Table 2. Upon heat-","rect":[187.56600952148438,333.0910339355469,560.6672399055486,323.059326171875]},{"page":6,"text":"ing, the CBOCOnSBA(CN) homologs (n = 4, 6, 8, and 10) showed the N phase, whereas","rect":[166.3168487548828,345.65069580078127,559.0118277796297,335.6190185546875]},{"page":6,"text":"CBOCO2SBA(CN) did not exhibit the LC phase. All the homologs exhibited the NTB and","rect":[166.3168487548828,358.1903991699219,559.0165234228635,348.1587219238281]},{"page":6,"text":"N phases upon cooling, similar to the CBCOOnSBA(CN) homologs. The NTB phase was","rect":[166.3168487548828,370.7301330566406,559.0162003843194,360.6984558105469]},{"page":6,"text":"characterized by typical blocky, striped, and focal-conic-like and rope-like textures in the","rect":[166.3168487548828,383.2698669433594,559.0173907111323,373.21826171875]},{"page":6,"text":"non-treated glass cells for n = 4, 6, and 8, respectively, as shown in Figure 5, which are","rect":[166.3168487548828,395.8095703125,559.0209099618525,385.7579650878906]},{"page":6,"text":"similar to those of CBCOOnSBA(CN). Figure 6 shows the DSC curves for CBCOOnSBA(CN)","rect":[166.3168487548828,408.34930419921877,560.0121997710629,398.2976989746094]},{"page":6,"text":"upon cooling. The shorter-spacer CBOCOnSBA(CN) dimers (n = 2 and 4) crystallized from","rect":[166.3168487548828,420.8890686035156,559.0132983214078,410.83746337890627]},{"page":6,"text":"the conventional N phase during DSC, and the crystallization peaks cover the N–NTB","rect":[166.3168487548828,433.42877197265627,558.5185728911787,423.3970947265625]},{"page":6,"text":"phase-transition peaks upon cooling in Figure 6. Therefore, their TNNTB values were de-","rect":[166.0179901123047,445.968505859375,560.6655309211736,435.9169006347656]},{"page":6,"text":"termined by POM. Figure 6 reveals the NTB phase of CBOCOnSBA(CN) with n = 6 and8","rect":[166.3168487548828,458.5082092285156,559.0205759520798,448.45660400390627]},{"page":6,"text":"vitrifed at approximately 10 ◦C. CBCOO10nSBA(CN) crystallized from the NTB phase.","rect":[166.03797912597657,471.0479736328125,547.8068169585274,460.9963684082031]},{"page":6,"text":"Table 2. Values of Tm upon heating, TIN, TNNTB, Tg, and TCr upon cooling at a rate of 10 ◦C min–1","rect":[166.02098083496095,496.2594299316406,558.8665090213034,484.86505126953127]},{"page":6,"text":"and their associated ∆H for CBOCOnSBA(CN).","rect":[166.31683349609376,507.676513671875,353.2942714471561,499.2391052246094]},{"page":6,"text":"Figure 5. Optical textures of the NTB phase of CBOCOnSBA(CN) in a non-treated glass cell upon","rect":[166.3168487548828,717.228515625,559.0175500530816,708.1820068359375]},{"page":6,"text":"cooling: (a) blocky texture for n = 4, (b) striped texture for n = 6, and (c) rope-like texture for n = 8. The","rect":[166.3168487548828,730.0369873046875,559.0177858121333,720.990478515625]},{"page":6,"text":"blocky texture of (a) CBOCO4SBA(CN) was recorded in a supercooled region that did not crystallize.","rect":[166.3168487548828,742.8453979492188,558.9716536684997,733.7988891601563]},{"page":7,"text":"Materials 2024, 17, 3278","rect":[35.699440002441409,57.948081970214847,116.46322882991832,50.886077880859378]},{"page":7,"text":"7 of 14","rect":[536.0813598632813,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":7,"text":"Figure 6. DSC curves of CBOCOnSBA(CN) upon cooling at a rate of 10 ◦C min−1.","rect":[166.3168487548828,317.0539855957031,489.9493007440311,306.4419250488281]},{"page":7,"text":"The TIN, TNNTB, and Tg values of CBCOOnSBA(CN) and CBOCOnSBA(CN) upon cooling","rect":[187.4420623779297,340.5068664550781,559.005860816254,329.6363525390625]},{"page":7,"text":"are plotted as a function of temperature in Figures 7a and 7b, respectively. Notably, the TIN","rect":[166.3218536376953,352.22772216796877,558.5142410548012,342.1761169433594]},{"page":7,"text":"values of CBCOOnSBA(CN) are remarkably lower than those of CBOCOnSBA(CN), which is","rect":[166.04298400878907,364.7674255371094,559.0141500988725,354.7158203125]},{"page":7,"text":"similar to the difference in those of previously reported CBCOOnSCB and CBOCOnSCB [33,77].","rect":[166.3218536376953,377.30718994140627,560.7592112995618,367.2555847167969]},{"page":7,"text":"This behavior could be attributed to a more bent molecular shape of CBCOOnSBA(CN)","rect":[166.00799560546876,389.8269958496094,560.0120885383611,379.7952880859375]},{"page":7,"text":"or a more anisotropic one of CBOCOnSBA(CN) [33,77]. The Ar–C–O bond angle in the","rect":[166.3168487548828,402.38665771484377,559.0196892587275,392.3350524902344]},{"page":7,"text":"COO ester linkage (109◦) is smaller than that of Ar–O–C in the OCO-ester linkage, similar","rect":[166.3168487548828,414.9263610839844,559.2170122303905,404.874755859375]},{"page":7,"text":"to Ar–O–C in the ether linkage. The smaller Ar–C–O bond angle results in a more bent","rect":[166.3168487548828,427.4660949707031,559.0121555468453,417.4344177246094]},{"page":7,"text":"molecular shape for CBCOOnSBA(CN) compared to that for CBOCOnSBA(CN). The more","rect":[166.3168487548828,439.9859313964844,559.0197022241365,429.9542236328125]},{"page":7,"text":"rigid COO ester than OCO facilitates the stronger biaxiality of CBCOOnSBA(CN) than that","rect":[166.3168487548828,452.5455322265625,559.0177747680896,442.4939270019531]},{"page":7,"text":"of CBOCOnSBA(CN) [33,77]. The entropy changes (∆SIN/R) at the I–N phase transition","rect":[166.3168487548828,465.08526611328127,559.0148493425945,455.0336608886719]},{"page":7,"text":"upon cooling scaled by the gas constant (R = 8.31 J K−1 mol−1), which are indicators of the","rect":[166.3168487548828,477.625,559.0113830021521,465.9561767578125]},{"page":7,"text":"molecular biaxiality [81], are plotted as a function of n in Figure 8. The ∆SIN/R values are","rect":[166.3168487548828,490.1637268066406,559.0150419115058,480.11212158203127]},{"page":7,"text":"remarkably lower for CBCOOnSBA(CN) than that for CBOCOnSBA(CN), indicating the","rect":[166.3168487548828,502.7034912109375,559.0184404682942,492.6518859863281]},{"page":7,"text":"stronger biaxiality or considerably more molecular bending of CBCOOnSBA(CN).","rect":[166.3168487548828,515.2431640625,526.6932305327462,505.19158935546877]},{"page":7,"text":"Figure 7. TIN, TNNTB, Tg, and TCr values as a function of n for (a) CBCOOnSBA(CN) and","rect":[166.3168487548828,688.7587280273438,559.0136712439446,678.9299926757813]},{"page":7,"text":"(b) CBOCOnSBA(CN) upon cooling.","rect":[166.02098083496095,700.784912109375,310.68846700379677,691.7562866210938]},{"page":7,"text":"In contrast, the TNNTB values of both the homologous series are comparable. A bent","rect":[187.56600952148438,723.4188842773438,559.014433098881,713.3673095703125]},{"page":7,"text":"geometry is advantageous, whereas a more linear molecular shape more likely to stabilize","rect":[166.3168487548828,735.9585571289063,559.019268696814,725.9268798828125]},{"page":7,"text":"the conventional N phase. Inducing the NTB phase in CBOCOnSBA(CN) requires more","rect":[166.3168487548828,748.498291015625,559.0179802743525,738.4666137695313]},{"page":7,"text":"supercooled conditions from the N phase upon cooling compared with inducing this phase","rect":[166.3168487548828,761.0380249023438,559.0118778487686,750.9864501953125]},{"page":7,"text":"in the more bent CBCOOnSBA(CN) [34,82]. Accordingly, the TNNTB values of more linear","rect":[166.3168487548828,773.5777587890625,559.2171211361033,763.5261840820313]},{"page":8,"text":"Materials 2024, 17, 3278","rect":[35.699440002441409,57.948081970214847,116.46322882991832,50.886077880859378]},{"page":8,"text":"8 of 14","rect":[536.0813598632813,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":8,"text":"CBOCOnSBA(CN) are comparable to those of more bent CBCOOnSBA(CN), in contrast","rect":[166.3168487548828,99.53614807128906,559.0145969530953,89.50447082519531]},{"page":8,"text":"to the trend observed for TIN values between both series. Tables 1 and 2 reveal that the","rect":[166.3168487548828,111.25112915039063,559.0119377938837,102.04420471191406]},{"page":8,"text":"TNNTB/TIN values used to indicate the supercooling degree of the NTB phase formation","rect":[165.70912170410157,124.63545989990235,559.0209528582195,114.58387756347656]},{"page":8,"text":"from TIN [83] are lower for CBOCOnSBA(CN) (0.82–0.85) than those for CBCOOnSBA(CN)","rect":[166.3168487548828,136.4985809326172,560.0123820597693,127.12373352050781]},{"page":8,"text":"(0.88–0.95).","rect":[165.98800659179688,149.03831481933595,214.94144525442585,139.68336486816407]},{"page":8,"text":"Figure 8. ∆SIN/R values as a function n for CBCOOnSBA(CN) (red circles) and CBOCOnSBA(CN)","rect":[166.3168487548828,296.2076416015625,559.9131840170076,287.31341552734377]},{"page":8,"text":"(blue squares) upon cooling.","rect":[166.02098083496095,309.1683044433594,278.47023580262489,300.1397399902344]},{"page":8,"text":"The TIN and TNNTB values of CBCOOnSBA(CN) decrease with decreasing n values","rect":[187.56600952148438,331.8023376464844,559.0168936975985,321.750732421875]},{"page":8,"text":"from 10 to 4 and marginally increase at n = 2. This reduction could be ascribed to the","rect":[166.3168487548828,344.3420715332031,559.01590507904,334.29046630859377]},{"page":8,"text":"enhanced effective molecular biaxiality or molecular bend for the shorter n and is partly","rect":[166.3168487548828,356.88177490234377,559.4080685793036,346.8301696777344]},{"page":8,"text":"supported by the ∆SIN/R trend, which decreases with descending n. The exception for","rect":[166.3168487548828,369.4215393066406,559.214035841006,359.36993408203127]},{"page":8,"text":"n = 2 could be attributed to its high rigidity owing to its short spacers.","rect":[166.3168487548828,381.9612731933594,473.5395745268868,371.9295959472656]},{"page":8,"text":"However,thetrendsofTIN andTNNTB valuesasafunctionofnforCBOCOnSBA(CN)differ","rect":[187.4420623779297,393.82421875,559.2031842049067,384.4493713378906]},{"page":8,"text":"from those for CBCOOnSBA(CN). Specifically, the TIN and TNNTB values of CBOCOnSBA(CN)","rect":[166.3218536376953,407.04071044921877,560.0046291589326,396.9891052246094]},{"page":8,"text":"are comparable or marginally increase with decreasing n and suddenly decrease at the short-","rect":[166.3168487548828,419.5804138183594,560.6694263335629,409.5487365722656]},{"page":8,"text":"est spacer (n = 2). These trends resemble those of the structurally similar cyanobiphenyl-","rect":[166.3168487548828,432.1201477050781,560.6732627349177,422.06854248046877]},{"page":8,"text":"based CBOCOnSCB [77] and ether-linked CBOnOCB [84]. The bond angle of Ar–O–C","rect":[166.3168487548828,444.6598815917969,559.0126308968152,434.6082763671875]},{"page":8,"text":"in the OCO-ester is similar to the ~118◦ bond angle in ether. Therefore, trends for n of","rect":[166.3168487548828,457.1995849609375,559.0158727180486,447.1479797363281]},{"page":8,"text":"OCO-ester-linked dimers are similar to those of ether-linked ones in terms of the molecular","rect":[166.3168487548828,467.1219787597656,559.216672974438,459.6877746582031]},{"page":8,"text":"shape (bend). The TIN and TNNTB values of the OCO-ester-linked and ether-linked dimers","rect":[166.3168487548828,482.2591857910156,559.0141401410091,472.22747802734377]},{"page":8,"text":"with shorter spacers are expected to be compensated by molecular anisotropy and fexibility","rect":[165.89805603027345,494.81884765625,559.4029555428165,484.7672424316406]},{"page":8,"text":"owing to the Ar–O–C ether bond. More anisotropy increases TIN, whereas more fexibility","rect":[166.3168487548828,507.3585510253906,559.4019594412464,497.30694580078127]},{"page":8,"text":"is likely to widen the conformations and distort the effective molecular bent shape of","rect":[166.3168487548828,519.8982543945313,559.0121495735174,509.8466796875]},{"page":8,"text":"OCO-linked dimers compared to those of the more bent COO-linked dimers.","rect":[166.3168487548828,532.4180297851563,504.1412896147774,522.3863525390625]},{"page":8,"text":"3.2. Photoinduced Phase Transitions","rect":[166.3168487548828,552.1233520507813,312.8684359960624,544.7289428710938]},{"page":8,"text":"The UV–visible spectra of n = 6 for both series before UV irradiation recorded in","rect":[187.56600952148438,570.3348999023438,559.0168024675945,560.30322265625]},{"page":8,"text":"dilute THF solutions are shown in Figure 9. These spectra are similar, exhibiting two main","rect":[166.3168487548828,582.8945922851563,559.0163978724897,572.8629150390625]},{"page":8,"text":"absorption peaks. A main band was observed at approximately 370 nm, attributed to the π–","rect":[166.3168487548828,595.4342651367188,560.5096597802418,585.402587890625]},{"page":8,"text":"π* transition of the benzylideneaniline moiety [34]. Because of the presence of the thioether","rect":[166.3168487548828,607.9740600585938,559.219846802563,597.9224853515625]},{"page":8,"text":"linkage and cyano group, the absorption wavelengths from the π–π* transitions are red-","rect":[166.3168487548828,620.5137329101563,560.6663854133611,610.462158203125]},{"page":8,"text":"shifted compared to around 310 nm of typical benzylideneanilines [85,86]. In addition,","rect":[166.3168487548828,633.0535278320313,560.2617582767937,623.001953125]},{"page":8,"text":"a peak at approximately 265 nm in their spectra may be ascribed to the σ–π* transition","rect":[166.3168487548828,645.5932006835938,559.0138727800945,635.5615234375]},{"page":8,"text":"of the benzylideneaniline moiety [85,86] and the π–π* transition of the cyanobiphenyl","rect":[166.3168487548828,658.1329345703125,559.017129261141,648.0813598632813]},{"page":8,"text":"moiety [87]. These results agree with those of previously reported thioether-linked N-","rect":[166.3168487548828,670.6726684570313,560.6688268196111,660.62109375]},{"page":8,"text":"benzylideneaniline-based LC dimers [34].","rect":[166.3168487548828,683.21240234375,349.42418756399618,673.1807250976563]},{"page":8,"text":"The photoinduced phase transitions of CBCOOnSBA(CN) and CBOCOnSBA(CN)","rect":[187.56600952148438,695.7322387695313,560.0120885383611,685.7005615234375]},{"page":8,"text":"were examined by irradiating UV light (365 nm and approximately 3 mW cm−2) to theN","rect":[165.89805603027345,708.2918701171875,559.0204369237885,696.660888671875]},{"page":8,"text":"and NTB phases of these dimers. This applied wavelength of the light source is appropriate","rect":[166.3168487548828,720.8316040039063,559.0116337081436,710.780029296875]},{"page":8,"text":"as the UV–visible absorption is observed at approximately 370 nm for the π–π* transition","rect":[166.3168487548828,733.371337890625,559.0114096684117,723.3197631835938]},{"page":8,"text":"of the benzylideneaniline moiety in both dimers. The optical textures of the LC phases of","rect":[166.3168487548828,745.9110717773438,559.0118071241259,735.8594970703125]},{"page":8,"text":"CBCOO6SBA(CN) when the UV light is turned on and off are shown in Figure 10. Upon","rect":[166.3168487548828,758.4508056640625,559.0206673473,748.3992309570313]},{"page":8,"text":"UV irradiation, the birefringent N phase texture changed to the dark textures of the Iso","rect":[166.3168487548828,770.9905395507813,559.01229042808,760.93896484375]},{"page":9,"text":"Materials 2024, 17, 3278","rect":[35.699440002441409,57.948081970214847,116.46322882991832,50.886077880859378]},{"page":9,"text":"9 of 14","rect":[536.0813598632813,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":9,"text":"phase, and the birefringent texture recovered after turning off the UV light, shown in","rect":[166.0179901123047,99.5560531616211,559.0180842058758,89.50447082519531]},{"page":9,"text":"Figure 10a,b, indicating a reversible photoinduced phase transition between the N and","rect":[166.3168487548828,112.09578704833985,559.0122262421558,102.06410217285156]},{"page":9,"text":"Iso phases. However, UV irradiation turned the blocky textures of the NTB phase into the","rect":[166.3168487548828,124.63545989990235,559.011965715868,114.58387756347656]},{"page":9,"text":"marble texture of the N phase, which then reversibly returned to the initial NTB phase","rect":[166.3168487548828,137.17532348632813,559.0163323251337,127.12373352050781]},{"page":9,"text":"texture after the UV irradiation was turned off, as shown in Figure 10c,d. This behavior","rect":[166.3168487548828,149.71505737304688,559.215256544131,139.66346740722657]},{"page":9,"text":"revealed a reversible photoinduced phase transition between the NTB and N phases. These","rect":[166.3168487548828,162.2348175048828,559.0117219781947,152.22303771972657]},{"page":9,"text":"photoinduced phase transition behaviors are similar to those observed for azobenzene-","rect":[166.0179901123047,174.77455139160157,560.6737096321111,164.7428741455078]},{"page":9,"text":"based twist–bend nematogenic dimers [75,76]. To the best of our knowledge, this is the","rect":[166.3168487548828,187.33419799804688,559.01346367279,177.28260803222657]},{"page":9,"text":"frst report of photoinduced phase transitions in imine-based LC dimers. However, the","rect":[166.3168487548828,199.85401916503907,559.012242969665,189.8223419189453]},{"page":9,"text":"temperature ranges for the transitions under UV light were strictly limited to 1 ◦C below the","rect":[166.3168487548828,212.41366577148438,559.0182865401748,202.36207580566407]},{"page":9,"text":"corresponding N or Iso phases. Similar azobenzene-based dimers exhibited photoinduced","rect":[166.3168487548828,224.95339965820313,559.0163417893133,214.9217071533203]},{"page":9,"text":"phase transitions within wider temperature ranges (~10 ◦C) using the same UV irradiation","rect":[166.0179901123047,237.49313354492188,559.0134182389389,227.46144104003907]},{"page":9,"text":"source. This difference could be ascribed to the energies of the isomerization process,","rect":[166.3168487548828,250.03280639648438,560.2615141361687,239.98121643066407]},{"page":9,"text":"as described in Section 1. The energy barrier of the trans-to-cis isomerization for the","rect":[166.3168487548828,262.5726623535156,559.02127617279,252.5210723876953]},{"page":9,"text":"imine bond is higher than that of the azo bond [46–48], which may prevent the imine","rect":[166.3168487548828,275.1122741699219,559.0159661141962,265.0606689453125]},{"page":9,"text":"bond isomerization at lower temperatures and narrow the possible photoinduced phase-","rect":[166.3168487548828,287.6321716308594,560.6686048070072,277.6203918457031]},{"page":9,"text":"transition temperature ranges. Additionally, the cis-to-trans relaxation of the imine bond is","rect":[166.3168487548828,300.1908264160156,559.0201611979424,290.13922119140627]},{"page":9,"text":"remarkably faster owing to its lower energy barrier (~16 kcal mol−1) compared to that of","rect":[166.3168487548828,312.7304992675781,559.0151016132047,301.06268310546877]},{"page":9,"text":"azobenzene (23 kcal mol−1) [45]. We also recorded the UV-visible spectra of the samples in","rect":[166.3168487548828,325.2503356933594,559.0114069373682,313.6024169921875]},{"page":9,"text":"a THF solution subjected to UV irradiation for 1–15 min at room temperature. No changes","rect":[166.3168487548828,337.8099670410156,559.0184126019466,327.75836181640627]},{"page":9,"text":"were observed in the UV–visible spectra, indicating that the N-benzylideneaniline moieties","rect":[165.89805603027345,350.3497009277344,559.016362568012,340.3180236816406]},{"page":9,"text":"exist in the trans form after UV irradiation, which agrees with the previously reported","rect":[166.3168487548828,362.8894348144531,559.018390792937,352.83782958984377]},{"page":9,"text":"results [45,46]. One possibility is that the N–Iso and NTB–N phase transitions of the imine-","rect":[166.3168487548828,375.4291687011719,560.6645807946732,365.3775634765625]},{"page":9,"text":"based dimers upon UV–light irradiation might have been caused by the heat generated","rect":[166.3168487548828,387.9689025878906,559.0122262421558,377.9372253417969]},{"page":9,"text":"during the UV irradiation, considering their limited temperature windows. However, the","rect":[166.3168487548828,400.50860595703127,559.0198117319916,390.4769287109375]},{"page":9,"text":"texture changed reversibly soon after switching on and off the light. In addition, extending","rect":[166.3168487548828,413.04833984375,559.0114404755727,402.9967346191406]},{"page":9,"text":"the UV irradiation time caused neither further changes in textures nor expansion of the","rect":[166.3168487548828,425.58807373046877,559.012242969665,415.5364685058594]},{"page":9,"text":"area. Therefore, the phase transitions upon UV irradiation could have been driven by the","rect":[166.3168487548828,438.1278076171875,559.0109369123724,428.0762023925781]},{"page":9,"text":"photoisomerization of the imine bond. Owing to the limitations of the apparatus, we could","rect":[166.0179901123047,450.66754150390627,559.015518550663,440.6159362792969]},{"page":9,"text":"not use incident light higher than approximately 3 mW cm−2. High-intensity light may","rect":[166.3168487548828,463.2072448730469,559.4083564622767,451.5772705078125]},{"page":9,"text":"expand the temperature range of photoinduced phase transitions and lead to the NTB–Iso","rect":[166.3168487548828,475.7469787597656,559.0160931340736,465.69537353515627]},{"page":9,"text":"phase transition, as observed for an azobenzene dimer [75].","rect":[166.0179901123047,488.2668151855469,426.97676935110555,478.235107421875]},{"page":9,"text":"0.4","rect":[189.3761444091797,516.6851806640625,205.9884409158702,507.9344787597656]},{"page":9,"text":"0.3","rect":[189.3761444091797,557.5739135742188,205.9884409158702,548.8111572265625]},{"page":9,"text":"0.2","rect":[189.3761444091797,598.4386596679688,205.9884409158702,589.6879272460938]},{"page":9,"text":"0.1","rect":[189.3761444091797,639.2957153320313,206.00965235753416,630.5274658203125]},{"page":9,"text":"0","rect":[199.4114990234375,680.1721801757813,206.0804056375499,671.4214477539063]},{"page":9,"text":"250","rect":[206.3882598876953,694.4570922851563,226.359000608253,685.7063598632813]},{"page":9,"text":"Figure 9.","rect":[166.3168487548828,734.3070068359375,205.88119695787169,725.6098022460938]},{"page":9,"text":"Non-normalized","rect":[219.31625366210938,733.0,286.6890252478509,725.4306640625]},{"page":9,"text":"UV–visible","rect":[292.4755859375,733.0,336.55583528534467,725.4306640625]},{"page":9,"text":"spectra","rect":[342.3423767089844,734.4413452148438,371.3117713571496,726.3711547851563]},{"page":9,"text":"of","rect":[377.1074523925781,733.0,385.1428090353851,725.4127807617188]},{"page":9,"text":"CBOCO6SBA(CN) (blue dashed line) in THF solution.","rect":[166.3168487548828,746.65869140625,380.478567101453,738.2391357421875]},{"page":10,"text":"Materials 2024, 17, 3278","rect":[35.699440002441409,57.948081970214847,116.46322882991832,50.886077880859378]},{"page":10,"text":"10 of 14","rect":[532.09814453125,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":10,"text":"Figure 10. POM images under UV irradiation for CBCOO6SBA(CN). Turning UV (a) on and (b) off at","rect":[166.3168487548828,382.8023986816406,559.0125491970365,373.75592041015627]},{"page":10,"text":"106.0 ◦C and turning UV (c) on and (d) off at 85.6 ◦C in a non-treated glass cell.","rect":[165.8680419921875,395.6108703613281,478.18675801942177,386.56439208984377]},{"page":10,"text":"4. Conclusions","rect":[166.31683349609376,413.5078430175781,233.28425848084465,406.18310546875]},{"page":10,"text":"We synthesized two homologous series of N-(4-cyanobenzylidene)aniline and cyanobiphenyl-","rect":[187.39207458496095,431.67962646484377,560.6690601226254,421.6280212402344]},{"page":10,"text":"based LC dimers with thioether and inverse ester linkages (COO and OCO, respectively).","rect":[166.3168487548828,444.2193603515625,560.7629900322346,434.18768310546877]},{"page":10,"text":"The dimers formed a monotropic NTB phase below the temperature of the conventional N","rect":[166.00799560546876,456.7392272949219,559.0184002916267,446.70751953125]},{"page":10,"text":"phase. Remarkably, the NTB phases of certain CBCOOnSBA(CN) and CBOCOnSBA(CN)","rect":[166.0179901123047,469.298828125,560.0118044763065,459.2472229003906]},{"page":10,"text":"homologs were stably supercooled to ambient temperatures and vitrifed. The LC phase-","rect":[166.3168487548828,481.83856201171877,560.6686658421635,471.7869567871094]},{"page":10,"text":"transition temperatures (TIN and TNNTB) and associated entropy changes (∆SIN) of the","rect":[166.3168487548828,494.3782653808594,559.01981132904,484.32666015625]},{"page":10,"text":"CBCOOnSBA(CN) homologs were lower than those of the CBOCOnSBA(CN) homologs","rect":[166.3168487548828,506.91796875,559.015984892035,496.8663635253906]},{"page":10,"text":"at the same n, which could be attributed to the more bent molecular geometry of the","rect":[166.3168487548828,519.4577026367188,559.0199333993525,509.4061279296875]},{"page":10,"text":"CBCOOnSBA(CN). UV irradiation transformed the NTB and N phases of the dimers into","rect":[166.3168487548828,531.9775390625,559.0162135685774,521.9458618164063]},{"page":10,"text":"the N and Iso phases, respectively. These phases reversibly returned to their initial phases","rect":[166.3168487548828,544.5371704101563,559.0180894895925,534.5054931640625]},{"page":10,"text":"after turning off the UV light. This study successfully demonstrates the photoinduced","rect":[166.3168487548828,557.076904296875,559.0121652069995,547.0253295898438]},{"page":10,"text":"phase transitions of N-benzylideneaniline-based LC dimers with the NTB phases, which","rect":[166.0179901123047,569.6166381835938,559.013750709782,559.5650634765625]},{"page":10,"text":"show a remarkable potential for photomobile LC materials.","rect":[166.3168487548828,582.136474609375,426.89721002493368,572.1047973632813]},{"page":10,"text":"Supplementary Materials: The following supporting information can be downloaded at: https:","rect":[166.3168487548828,605.83544921875,560.1336993992779,596.7889404296875]},{"page":10,"text":"//www.mdpi.com/article/10.3390/ma17133278/s1.","rect":[165.23236083984376,617.8347778320313,374.39317891785927,608.8240966796875]},{"page":10,"text":"Author Contributions: Conceptualization, Y.A. (Yuki Arakawa); Methodology, Y.A. (Yuki Arakawa);","rect":[165.9669952392578,635.5280151367188,560.1330896402219,626.4993896484375]},{"page":10,"text":"Validation, Y.A. (Yuki Arakawa); Formal analysis, Y.A. (Yuki Arakawa); Investigation, Y.A. (Yuki","rect":[165.9940185546875,647.2316284179688,559.0138714620877,638.2030029296875]},{"page":10,"text":"Arakawa) and Y.A. (Yuto Arai); Resources, Y.A. (Yuki Arakawa); Data curation, Y.A. (Yuki Arakawa);","rect":[165.9669952392578,658.326171875,560.132758958944,649.9066162109375]},{"page":10,"text":"Writing—Original Draft Preparation, Y.A. (Yuki Arakawa); Writing—Review and Editing, Y.A. (Yuki","rect":[165.8680419921875,670.6388549804688,559.0137560145189,661.5923461914063]},{"page":10,"text":"Arakawa) and Y.A. (Yuto Arai); Visualization, Y.A. (Yuki Arakawa); Supervision, Y.A. (Yuki Arakawa);","rect":[165.9669952392578,682.3245239257813,560.1391087652216,673.3138427734375]},{"page":10,"text":"Project Administration, Y.A. (Yuki Arakawa); Funding Acquisition, Y.A. (Yuki Arakawa). All authors","rect":[166.3168487548828,694.0460815429688,559.0200135156167,685.0174560546875]},{"page":10,"text":"have read and agreed to the published version of the manuscript.","rect":[166.3168487548828,705.7496948242188,424.68935201356239,696.7031860351563]},{"page":10,"text":"Funding: This research was funded by JSPS KAKENHI Grant number 20K15351.","rect":[166.3168487548828,723.4249877929688,486.4655360955936,714.3784790039063]},{"page":10,"text":"Data Availability Statement: Data are presented in the article and Supplementary Materials.","rect":[166.3168487548828,741.1002807617188,533.5972499627811,732.0716552734375]},{"page":10,"text":"Conficts of Interest: The authors declare no conficts of interest.","rect":[166.3168487548828,756.4188842773438,421.69411275574989,749.7280883789063]},{"page":11,"text":"Materials 2024, 17, 3278","rect":[35.699440002441409,57.948081970214847,116.46322882991832,50.886077880859378]},{"page":11,"text":"11 of 14","rect":[532.09814453125,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":11,"text":"References","rect":[35.699440002441409,96.90880584716797,85.4793878753759,89.5840835571289]},{"page":11,"text":"1.","rect":[35.699440002441409,111.24813842773438,42.42112157532996,105.01412200927735]},{"page":11,"text":"2.","rect":[35.69944763183594,134.23788452148438,42.421129204724497,128.04864501953126]},{"page":11,"text":"3.","rect":[35.699432373046878,157.37879943847657,42.42111394593543,151.03729248046876]},{"page":11,"text":"4.","rect":[35.69944381713867,180.21621704101563,42.42112539002723,173.98220825195313]},{"page":11,"text":"5.","rect":[35.69944381713867,203.3581085205078,42.42112539002723,197.0166015625]},{"page":11,"text":"6.","rect":[35.69943618774414,226.34779357910157,42.4211177606327,220.00628662109376]},{"page":11,"text":"7.","rect":[35.69950866699219,237.68936157226563,42.421190239880747,231.5001220703125]},{"page":11,"text":"8.","rect":[35.699432373046878,260.8313293457031,42.42111394593543,254.48980712890626]},{"page":11,"text":"9.","rect":[35.699462890625,283.8210754394531,42.421144463513559,277.47955322265627]},{"page":11,"text":"10.","rect":[35.699462890625,306.8106384277344,46.90226552674598,300.4243469238281]},{"page":11,"text":"11.","rect":[35.69944763183594,329.6480407714844,46.902250267956919,323.4140319824219]},{"page":11,"text":"12.","rect":[35.699432373046878,364.131591796875,46.90223500916785,357.8975830078125]},{"page":11,"text":"13.","rect":[35.69944763183594,387.2735595703125,46.902250267956919,380.88726806640627]},{"page":11,"text":"14.","rect":[35.699462890625,398.6161193847656,46.90226552674598,392.3821105957031]},{"page":11,"text":"15.","rect":[35.69944763183594,421.758056640625,46.902250267956919,415.37176513671877]},{"page":11,"text":"16.","rect":[35.699432373046878,444.7467346191406,46.90223500916785,438.3604431152344]},{"page":11,"text":"17.","rect":[35.699440002441409,456.0892639160156,46.902242638562388,449.8552551269531]},{"page":11,"text":"18.","rect":[35.69941711425781,479.2312316894531,46.90221975037879,472.8449401855469]},{"page":11,"text":"19.","rect":[35.69943618774414,513.7156982421875,46.90223882386512,507.3294372558594]},{"page":11,"text":"20.","rect":[35.69944763183594,536.704345703125,46.902250267956919,530.3628540039063]},{"page":11,"text":"21.","rect":[35.69943618774414,571.03662109375,46.90223882386512,564.8025512695313]},{"page":11,"text":"22.","rect":[35.699462890625,594.0263061523438,46.90226552674598,587.8370361328125]},{"page":11,"text":"23.","rect":[35.699440002441409,617.168212890625,46.902242638562388,610.8267211914063]},{"page":11,"text":"24.","rect":[35.699440002441409,628.5108642578125,46.902242638562388,622.2767944335938]},{"page":11,"text":"25.","rect":[35.69944763183594,651.6517333984375,46.902250267956919,645.3102416992188]},{"page":11,"text":"26.","rect":[35.69947814941406,674.6414184570313,46.90228078553504,668.2999267578125]},{"page":11,"text":"27.","rect":[35.69947814941406,697.4788818359375,46.90228078553504,691.2896118164063]},{"page":11,"text":"28.","rect":[35.69943618774414,720.6207275390625,46.90223882386512,714.2792358398438]},{"page":11,"text":"29.","rect":[35.69944763183594,743.6094360351563,46.902250267956919,737.2679443359375]},{"page":11,"text":"Tazuke, S.; Kurihara, S.; Ikeda, T. Amplifed image recording in liquid crystal media by means of photochemically triggered","rect":[57.20546340942383,113.75613403320313,559.0180657751946,104.70964813232422]},{"page":11,"text":"phase transition. Chem. Lett. 1987, 16, 911–914. [CrossRef]","rect":[56.936588287353519,125.2330322265625,284.66527376683077,116.15967559814453]},{"page":11,"text":"Eich, M.; Wendorff, J.H.; Reck, B.; Ringsdorf, H. Reversible digital and holographic optical storage in polymeric liquid crystals.","rect":[57.20546340942383,136.74581909179688,560.5823549676916,127.69933319091797]},{"page":11,"text":"Makromol. Chem. Rapid Commun. 1987, 8, 59–63. [CrossRef]","rect":[57.20546340942383,148.17689514160157,288.115285973862,139.1483154296875]},{"page":11,"text":"Ikeda, T.; Tsutsumi, O. Optical switching and image storage by means of azobenzene liquid-crystal flms. Science 1995, 268,","rect":[57.20546340942383,159.73446655273438,560.1365680516217,150.68797302246095]},{"page":11,"text":"1873–1875. [CrossRef]","rect":[56.75667190551758,170.3426055908203,143.56494722874479,162.18284606933595]},{"page":11,"text":"Rochon, P.; Batalla, E.; Natansohn, A. Optically induced surface gratings on azoaromatic polymer flms. Appl. Phys. Lett. 1995, 66,","rect":[57.20546340942383,182.72415161132813,560.1366750996384,173.63287353515626]},{"page":11,"text":"136–138. [CrossRef]","rect":[56.75667190551758,193.33216857910157,134.60271273167448,185.1724090576172]},{"page":11,"text":"Finkelmann, H.; Nishikawa, E.; Pereira, G.G.; Warner, M. A new opto-mechanical effect in solids. Phys. Rev. Lett. 2001, 87, 015501.","rect":[57.20546340942383,205.69586181640626,560.5864431660447,196.62249755859376]},{"page":11,"text":"[CrossRef]","rect":[57.20546340942383,216.3218536376953,98.66478548558072,208.16209411621095]},{"page":11,"text":"Yu, Y.; Nakano, M.; Ikeda, T. Directed bending of a polymer flm by light. Nature 2003, 425, 145. [CrossRef]","rect":[57.20881652832031,228.70346069335938,476.94737825901827,219.65696716308595]},{"page":11,"text":"Mahimwalla, Z.; Yager, K.G.; Mamiya, J.I.; Shishido, A.; Priimagi, A.; Barrett, C.J. Azobenzene photomechanics: Prospects and","rect":[57.20546340942383,240.19729614257813,559.0139208842844,231.16871643066407]},{"page":11,"text":"potential applications. Polym. Bull. 2012, 69, 967–1006. [CrossRef]","rect":[56.936588287353519,251.67425537109376,314.9474392941745,242.60089111328126]},{"page":11,"text":"Lugger, S.J.; Ceamanos, L.; Mulder, D.J.; Sánchez-Somolinos, C.; Schenning, A.P.H.J. 4D printing of supramolecular liquid crystal","rect":[57.20546340942383,263.1869812011719,559.0201696268966,254.14048767089845]},{"page":11,"text":"elastomer actuators fueled by light. Adv. Funct. Mater. 2023, 8, 2201472. [CrossRef]","rect":[57.20546340942383,274.6818542480469,382.208059411362,265.590576171875]},{"page":11,"text":"Ichimura, K.; Suzuki, Y.; Seki, T.; Hosoki, A.; Aoki, K. Reversible change in alignment mode of nematic liquid crystals regulated","rect":[57.20546340942383,286.1766662597656,559.0148608365253,277.13018798828127]},{"page":11,"text":"photochemically by command surfaces modifed with an azobenzene monolayer. Langmuir 1988, 4, 1214–1216. [CrossRef]","rect":[56.936588287353519,297.6714172363281,537.4864407590183,288.62493896484377]},{"page":11,"text":"Fukuhara, K.; Nagano, S.; Hara, M.; Seki, T. Free-surface molecular command systems for photoalignment of liquid crystalline","rect":[57.20546340942383,309.1662902832031,559.0119896278626,300.11981201171877]},{"page":11,"text":"materials. Nat. Commun. 2014, 5, 3320. [CrossRef]","rect":[57.20546340942383,319.7744445800781,252.48161898167448,311.61468505859377]},{"page":11,"text":"Akiyama, H.; Kanazawa, S.; Okuyama, Y.; Yoshida, M.; Kihara, H.; Nagai, H.; Norikane, Y.; Azumi, R. Photochemically reversible","rect":[57.20546340942383,332.156005859375,559.0152424857906,323.12744140625]},{"page":11,"text":"liquefaction and solidifcation of multiazobenzene sugar-alcohol derivatives and application to reworkable adhesives. ACS Appl.","rect":[57.20546340942383,343.64984130859377,560.1407978347393,334.5585632324219]},{"page":11,"text":"Mater. Interfaces 2014, 6, 7933–7941. [CrossRef]","rect":[57.20546340942383,355.08203125,239.38768587620573,346.0534362792969]},{"page":11,"text":"Wu, Z.; Ji, C.; Zhao, X.; Han, Y.; Müllen, K.; Pan, K.; Yin, M. Green-light-triggered phase transition of azobenzene derivatives","rect":[57.20546340942383,366.6395263671875,559.0178972475816,357.5930480957031]},{"page":11,"text":"toward reversible adhesives. J. Am. Chem. Soc. 2019, 141, 7385–7390. [CrossRef]","rect":[57.20546340942383,377.4447326660156,369.8231717160495,369.0431213378906]},{"page":11,"text":"Hartley, G.S. The cis-form of azobenzene. Nature 1937, 140, 281. [CrossRef]","rect":[57.20882797241211,389.62921142578127,351.38756380589327,380.5827331542969]},{"page":11,"text":"Tsutsumi, O.; Shiono, T.; Ikeda, T.; Galli, G. Photochemical phase transition behavior of nematic liquid crystals with azobenzene","rect":[57.20546340942383,401.1240234375,559.0191706396339,392.0775451660156]},{"page":11,"text":"moieties as both mesogens and photosensitive chromophores. J. Phys. Chem. B 1997, 101, 1332–1337. [CrossRef]","rect":[57.20546340942383,412.618896484375,495.983694176987,403.5276184082031]},{"page":11,"text":"Wen, Y.; Zheng, Z.; Wang, H.; Shen, D. Photoinduced phase transition behaviours of the liquid crystal blue phase doped with","rect":[57.20546340942383,424.11370849609377,559.0185027803525,415.0672302246094]},{"page":11,"text":"azobenzene bent-shaped molecules. Liq. Cryst. 2012, 39, 509–514. [CrossRef]","rect":[57.20546340942383,435.5896301269531,357.8943081906589,426.5610656738281]},{"page":11,"text":"Ikeda, T. Photomodulation of liquid crystal orientations for photonic applications. J. Mater. Chem. 2003, 13, 2037–2057. [CrossRef]","rect":[57.20546340942383,447.1023864746094,559.0129086734808,438.0111083984375]},{"page":11,"text":"Yamamoto, T.; Nishiyama, I.; Yokoyama, H.H. Novel photoinduced phase transition observed in three-dimensional liquid-","rect":[57.20546340942383,458.5971984863281,560.5080434103851,449.5686340332031]},{"page":11,"text":"crystalline phase of azobenzene compound. Chem. Lett. 2007, 36, 1108–1109. [CrossRef]","rect":[57.20546340942383,470.0920715332031,401.0916958859714,461.00079345703127]},{"page":11,"text":"Hori, R.; Furukawa, D.; Yamamoto, K.; Kutsumizu, S. Light-driven phase transition in a cubic-phase-forming binary system","rect":[57.20546340942383,481.5868835449219,559.0181000575466,472.5404052734375]},{"page":11,"text":"composed of 4′-n-Docosyloxy-3′-nitrobiphenyl-4-carboxylic acid and an azobenzene derivative. Chem. Eur. J. 2012, 18, 7346–7350.","rect":[57.20546340942383,493.0816955566406,560.5868526473087,483.2464904785156]},{"page":11,"text":"[CrossRef]","rect":[57.20546340942383,503.6898498535156,98.66478548558072,495.53009033203127]},{"page":11,"text":"Alaasar, M.; Poppe, S.; Dong, Q.; Liu, F.; Tschierske, C. Isothermal chirality switching in liquid-crystalline azobenzene compounds","rect":[57.20546340942383,516.0714111328125,559.013114500972,507.0428161621094]},{"page":11,"text":"with non-polarized light. Angew. Chem. Int. Ed. 2017, 56, 10801–10805. [CrossRef]","rect":[56.828636169433597,527.5662841796875,377.88084993870577,518.4749755859375]},{"page":11,"text":"Wang, M.; Hu, W.; Wang, L.; Guo, D.Y.; Lin, T.H.; Zhang, L.; Yang, H. Reversible light-directed self-organized 3D liquid crystalline","rect":[57.20546340942383,539.06005859375,559.0130250699458,530.0135498046875]},{"page":11,"text":"photonic nanostructures doped with azobenzene-functionalized bent-shaped molecules. J. Mater. Chem. C 2018, 6, 7740–7744.","rect":[56.936588287353519,550.5369873046875,560.5852985203717,541.463623046875]},{"page":11,"text":"[CrossRef]","rect":[57.20546340942383,561.1629638671875,98.66478548558072,553.0032348632813]},{"page":11,"text":"Alaasar, M.; Cai, X.; Kraus, F.; Giese, M.; Liu, F.; Tschierske, C. Controlling ambidextrous mirror symmetry breaking in","rect":[57.20546340942383,573.5445556640625,559.0178552288628,564.5159301757813]},{"page":11,"text":"photosensitive supramolecular polycatenars by alkyl-chain engineering. J. Mol. Liq. 2022, 351, 118597. [CrossRef]","rect":[56.936588287353519,585.0394287109375,503.070852380112,575.9481201171875]},{"page":11,"text":"Norikane, Y.; Hirai, Y.; Yoshida, M. Photoinduced isothermal phase transitions of liquid-crystalline macrocyclic azobenzenes.","rect":[57.20546340942383,596.5342407226563,560.5812091649029,587.4877319335938]},{"page":11,"text":"Chem. Commun. 2011, 47, 1770–1772. [CrossRef]","rect":[56.909603118896487,607.142333984375,244.38937960179167,598.9378051757813]},{"page":11,"text":"Goldmacher, J.; Barton, L.A. Liquid crystals. I. Fluorinated anils. J. Org. Chem. 1967, 32, 476–477. [CrossRef]","rect":[57.20882034301758,619.52392578125,480.90025911839327,610.4326171875]},{"page":11,"text":"Castellano, J.A.; Goldmacher, J.E.; Barton, L.A.; Kane, J.S. Liquid crystals. II. Effects of terminal group substitution on the","rect":[57.20546340942383,631.0177612304688,559.0178714181571,621.9712524414063]},{"page":11,"text":"mesomorphic behavior of some benzylideneanilines. J. Org. Chem. 1968, 33, 3501–3504. [CrossRef]","rect":[57.20546340942383,642.5125732421875,444.5585232785495,633.4212646484375]},{"page":11,"text":"Kitamura, T.; Mukoh, A.; Isogai, M.; Inukai, T.; Furukawa, K.; Terashima, K. Synthesis and some properties of low melting","rect":[57.20546340942383,654.0074462890625,559.0179695343067,644.9609375]},{"page":11,"text":"ferroelectric liquid crystals of benzylidene anilines. Mol. Cryst. Liq. Cryst. 1986, 136, 167–173. [CrossRef]","rect":[57.20546340942383,665.5023193359375,467.33959017308077,656.4110107421875]},{"page":11,"text":"Date, R.W.; Imrie, C.T.; Luckhurst, G.R.; Seddon, J.M. Smectogenic dimeric liquid crystals. The preparation and properties of the","rect":[57.20546340942383,676.9971313476563,559.0137787015325,667.9506225585938]},{"page":11,"text":"α, ω-bis (4-n-alkylanilinebenzylidine-4′-oxy) alkanes. Liq. Cryst. 1992, 12, 203–238. [CrossRef]","rect":[57.20546340942383,688.491943359375,427.3841153195651,678.6566772460938]},{"page":11,"text":"Blumstein, A.; Blumstein, R.B.; Clough, S.B.; Hsu, E.C. Oriented polymer growth in thermotropic mesophases. Macromolecules","rect":[57.20546340942383,699.9867553710938,559.0155065159635,690.8954467773438]},{"page":11,"text":"1975, 8, 73–76. [CrossRef]","rect":[56.75667190551758,710.5948486328125,157.00812349827604,702.4351196289063]},{"page":11,"text":"Niori, T.; Sekine, T.; Watanabe, J.; Furukawa, T.; Takezoe, H. Distinct ferroelectric smectic liquid crystals consisting of banana","rect":[57.20546340942383,722.9764404296875,559.0180701852746,713.929931640625]},{"page":11,"text":"shaped achiral molecules. J. Mater. Chem. 1996, 6, 1231–1233. [CrossRef]","rect":[57.20546340942383,734.4523315429688,340.39183626683077,725.3789672851563]},{"page":11,"text":"Paul, M.K.; Saha, S.K.; Kalita, G.; Bhattacharya, B.; Sarkar, U. Low-temperature nematic phase in azo functionalised reactive","rect":[57.20546340942383,745.9651489257813,559.0178714181571,736.9186401367188]},{"page":11,"text":"hockey stick mesogens possessing lateral methyl group. Dyes Pigm. 2020, 173, 107233. [CrossRef]","rect":[57.20546340942383,757.4599609375,439.79015169651827,748.4134521484375]},{"page":12,"text":"Materials 2024, 17, 3278","rect":[35.699440002441409,57.948081970214847,116.46322882991832,50.886077880859378]},{"page":12,"text":"12 of 14","rect":[532.09814453125,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":12,"text":"30.","rect":[35.699440002441409,96.91975402832031,46.902242638562388,90.57825469970703]},{"page":12,"text":"31.","rect":[35.69943618774414,131.4042510986328,46.90223882386512,125.0179672241211]},{"page":12,"text":"32.","rect":[35.69943618774414,165.8877716064453,46.90223882386512,159.5462646484375]},{"page":12,"text":"33.","rect":[35.69941711425781,188.87745666503907,46.90221975037879,182.53594970703126]},{"page":12,"text":"34.","rect":[35.699440002441409,211.8671417236328,46.902242638562388,205.48086547851563]},{"page":12,"text":"35.","rect":[35.699440002441409,234.85682678222657,46.902242638562388,228.51531982421876]},{"page":12,"text":"36.","rect":[35.699440002441409,257.8454895019531,46.902242638562388,251.50396728515626]},{"page":12,"text":"37.","rect":[35.699440002441409,292.3299865722656,46.902242638562388,285.98846435546877]},{"page":12,"text":"38.","rect":[35.69944763183594,315.3196716308594,46.902250267956919,308.9781494140625]},{"page":12,"text":"39.","rect":[35.69944763183594,338.309326171875,46.902250267956919,331.9678039550781]},{"page":12,"text":"40.","rect":[35.69944763183594,361.2980651855469,46.902250267956919,354.9117736816406]},{"page":12,"text":"41.","rect":[35.699432373046878,384.1354064941406,46.90223500916785,377.9013977050781]},{"page":12,"text":"42.","rect":[35.69947814941406,407.1250915527344,46.90228078553504,400.8910827636719]},{"page":12,"text":"43.","rect":[35.69943618774414,441.7618713378906,46.90223882386512,435.3755798339844]},{"page":12,"text":"44.","rect":[35.69944763183594,464.5982666015625,46.902250267956919,458.3642578125]},{"page":12,"text":"45.","rect":[35.69947814941406,476.24542236328127,46.90228078553504,469.859130859375]},{"page":12,"text":"46.","rect":[35.69950866699219,487.740234375,46.902311303113169,481.35394287109377]},{"page":12,"text":"47.","rect":[35.69944763183594,510.5776062011719,46.902250267956919,504.3435974121094]},{"page":12,"text":"48.","rect":[35.69943618774414,545.21435546875,46.90223882386512,538.8280639648438]},{"page":12,"text":"49.","rect":[35.69944763183594,568.2030029296875,46.902250267956919,561.8167114257813]},{"page":12,"text":"50.","rect":[35.699432373046878,591.1926879882813,46.90223500916785,584.8511962890625]},{"page":12,"text":"51.","rect":[35.699462890625,614.182373046875,46.90226552674598,607.7960815429688]},{"page":12,"text":"52.","rect":[35.69941711425781,637.1720581054688,46.90221975037879,630.83056640625]},{"page":12,"text":"53.","rect":[35.69943618774414,671.6555786132813,46.90223882386512,665.3140869140625]},{"page":12,"text":"54.","rect":[35.69944763183594,694.6452026367188,46.902250267956919,688.2589111328125]},{"page":12,"text":"55.","rect":[35.699440002441409,717.6348876953125,46.902242638562388,711.2933959960938]},{"page":12,"text":"56.","rect":[35.699440002441409,740.6245727539063,46.902242638562388,734.2830810546875]},{"page":12,"text":"Yeap, G.Y.; Ha, S.T.; Lim, P.L.; Boey, P.L.; Ito, M.M.; Sanehisa, S.; Youhei, Y. Synthesis, physical and mesomorphic properties of","rect":[57.20546340942383,99.27542114257813,559.0150455418,90.22893524169922]},{"page":12,"text":"Schiff’s base esters containing ortho-, meta- and para-substituents in benzylidene-4′-alkanoyloxyanilines. Liq. Cryst. 2006, 33,","rect":[57.20546340942383,110.77029418945313,560.1361150330943,100.93506622314453]},{"page":12,"text":"205–211. [CrossRef]","rect":[57.20546340942383,121.37837219238281,135.05148897679167,113.21862030029297]},{"page":12,"text":"Kosaka, Y.; Kato, T.; Uryu, T. Synthesis and the smectic mesophase of copolymers containing a mesogenic (carbazolylmethylene)","rect":[57.20546340942383,133.75991821289063,559.9101487106785,124.71343231201172]},{"page":12,"text":"aniline group as the electron donor and a (4’-nitrobenzylidene) aniline group as the electron acceptor. Macromolecules 1994, 27,","rect":[57.20546340942383,145.25479125976563,560.1366488681669,136.16351318359376]},{"page":12,"text":"2658–2663. [CrossRef]","rect":[57.20546340942383,155.86293029785157,144.01373873265104,147.7031707763672]},{"page":12,"text":"Fritsch, L.; Lavayen, V.; Merlo, A.A. Photochemical behaviour of Schiff base liquid crystals based on isoxazole and isoxazoline","rect":[57.20546340942383,168.24337768554688,559.0139225295973,159.19688415527345]},{"page":12,"text":"ring. A kinetic approach. Liq. Cryst. 2018, 45, 1802–1812. [CrossRef]","rect":[57.20546340942383,179.73825073242188,323.5876065305026,170.69175720214845]},{"page":12,"text":"Arakawa, Y.; Komatsu, K.; Inui, S.; Tsuji, H. Thioether-linked liquid crystal dimers and trimers: The twist-bend nematic phase. J.","rect":[57.20546340942383,191.23312377929688,560.1367594902638,182.2045440673828]},{"page":12,"text":"Mol. Struct. 2020, 1199, 126913. [CrossRef]","rect":[57.20546340942383,201.8412628173828,223.41750155003386,193.63671875]},{"page":12,"text":"Arakawa, Y.; Ishida, Y.; Komatsu, K.; Arai, Y.; Tsuji, H. Thioether-linked benzylideneaniline-based twist-bend nematic liquid","rect":[57.20546340942383,214.22280883789063,559.0179437048821,205.19422912597657]},{"page":12,"text":"crystal dimers: Insights into spacer lengths, mesogenic arm structures, and linkage types. Tetrahedron 2021, 95, 132351. [CrossRef]","rect":[57.20546340942383,225.71762084960938,558.8740661727698,216.6263427734375]},{"page":12,"text":"Perju, E.; Marin, L. Mesomorphic behavior of symmetric azomethine dimers containing different chromophore groups. Molecules","rect":[57.20546340942383,237.21249389648438,559.0169031630746,228.1212158203125]},{"page":12,"text":"2021, 26, 2183. [CrossRef]","rect":[57.20546340942383,247.82057189941407,157.4567013791354,239.6608123779297]},{"page":12,"text":"Cruickshank, E.; Walker, R.; Strachan, G.J.; Goode, C.H.; Majewska, M.M.; Pociecha, D.; Gorecka, E.; Storey, J.M.; Imrie, C.T. The","rect":[57.20546340942383,260.2011413574219,559.0158951471418,251.1725616455078]},{"page":12,"text":"infuence of the imine bond direction on the phase behaviour of symmetric and non-symmetric liquid crystal dimers. J. Mol. Liq.","rect":[57.20546340942383,271.6959533691406,560.1383464043263,262.60467529296877]},{"page":12,"text":"2023, 391, 123226. [CrossRef]","rect":[57.20546340942383,282.3040466308594,170.8998623898776,274.144287109375]},{"page":12,"text":"Chakraborty, A.; Bhattacharjee, D.; Alapati, P.R.; Bhattacharjee, A. Theoretical investigation of N (pn alkyloxy benzylidene) pn","rect":[57.20546340942383,294.6856384277344,559.0133678424143,285.63916015625]},{"page":12,"text":"alkyl aniline Schiff-based liquid crystal molecule. Phys. Rev. B Condens. Matter 2024, 681, 415857. [CrossRef]","rect":[57.20546340942383,306.1804504394531,481.29393587620577,297.08917236328127]},{"page":12,"text":"Omar, A.Z.; El-Atawy, M.A.; Alsubaie, M.S.; Alazmi, M.L.; Ahmed, H.A.; Hamed, E.A. Synthesis and computational investigations","rect":[57.20546340942383,317.6753234863281,559.0129924306596,308.6467590332031]},{"page":12,"text":"of new thioether/azomethine liquid crystal derivatives. Crystals 2023, 13, 378. [CrossRef]","rect":[57.20546340942383,329.1701354980469,408.50304232151827,320.078857421875]},{"page":12,"text":"Katariya, K.; Patil, J.; Nakum, K.; Nada, S.; Hagar, M.; Soni, R. Biphenyl based Schiff base derivatives of 6-aminocoumarin:","rect":[57.20546340942383,340.6650390625,560.1330890477154,331.6185607910156]},{"page":12,"text":"Design, synthesis, mesomorphic properties and DFT studies. J. Mol. Struct. 2024, 1311, 138395. [CrossRef]","rect":[57.20546340942383,352.15985107421877,474.12425814183077,343.0685729980469]},{"page":12,"text":"Martínez, D.; Schlossarek, T.; Würthner, F.; Soberats, B. Isothermal phase transitions in liquid crystals driven by dynamic covalent","rect":[57.20546340942383,363.6537170410156,559.012671267349,354.6251525878906]},{"page":12,"text":"chemistry. Angew. Chem. Int. Ed. 2024, 63, e202403910. [CrossRef] [PubMed]","rect":[57.20546340942383,375.1485290527344,356.9637051633151,366.0572509765625]},{"page":12,"text":"Chakraborty, A.; Bhattacharjee, D.; Bhattacharjee, A. Exploring odd-even sensitivity in m.OnO.m liquid crystal compounds: A","rect":[57.20546340942383,386.6433410644531,559.3659291031597,377.6147766113281]},{"page":12,"text":"comprehensive study using DFT analysis. J. Mol. Liq. 2024, 403, 124800. [CrossRef]","rect":[57.20546340942383,398.1382141113281,383.257375817612,389.04693603515627]},{"page":12,"text":"Soni, R.; Nakum, K.J.; Katariya, K.D.; Gergis, M.; Hagar, M.; Sharma, V.S. Biphenyls embedded Schiff base-bis esters: Self-","rect":[57.20546340942383,409.6330261230469,560.5080434103851,400.5865478515625]},{"page":12,"text":"assembling behaviour, impact of additional aromatic ring and ester linkage and their DFT investigations. Liq. Cryst. 2024.","rect":[57.20546340942383,421.12786865234377,560.5843829930279,412.0813903808594]},{"page":12,"text":"[CrossRef]","rect":[57.20546340942383,431.7359924316406,98.66478548558072,423.57623291015627]},{"page":12,"text":"Rabari, M.; Bhatt, M.; Prajapati, A.K. Symmetrical liquid crystalline dimers containing azo and azomethine linkages: Synthesis,","rect":[57.20546340942383,444.1175231933594,560.1395117964028,435.0889587402344]},{"page":12,"text":"characterisation, mesomorphic study and DFT studies. Liq. Cryst. 2024. [CrossRef]","rect":[57.20546340942383,455.61138916015627,383.0140591672214,446.5649108886719]},{"page":12,"text":"Kuhn, R.; Weitz, H.M. Photochemistry of triphenylformazan. Chem. Ber. 1953, 86, 1199–1212. [CrossRef]","rect":[57.20882797241211,467.106201171875,466.4444180539401,458.0149230957031]},{"page":12,"text":"Fischer, E.; Frei, Y. Photoisomerization equilibria involving the C=N Double bond. J. Chem. Phys. 1957, 27, 808–809. [CrossRef]","rect":[57.208858489990237,478.60107421875,554.622121911362,469.5097961425781]},{"page":12,"text":"Maeda, K.; Fischer, E. Photoformation of “Z”(cis) isomers in diaryl- and triaryl-Azomethines, Part II. 1 electronic and NMR","rect":[57.20546340942383,490.09588623046877,559.0180123729956,481.0494079589844]},{"page":12,"text":"spectra of methyl derivatives of benzylideneaniline (C6H5—CH= N—C6H5). Isr. J. Chem. 1977, 16, 294–298. [CrossRef]","rect":[57.20546340942383,501.5906982421875,527.134817223862,492.4994201660156]},{"page":12,"text":"Gahl, C.; Brete, D.; Leyssner, F.; Koch, M.; McNellis, E.R.; Mielke, J.; Carley, R.; Grill, L.; Reuter, K.; Tegeder, P.; et al. Coverage-","rect":[57.20546340942383,513.0855712890625,560.5039981785187,504.0569763183594]},{"page":12,"text":"and temperature-controlled isomerization of an imine derivative on Au(111). J. Am. Chem. Soc. 2013, 135, 4273–4281. [CrossRef]","rect":[57.20546340942383,524.5625,559.0207676541263,515.4891357421875]},{"page":12,"text":"[PubMed]","rect":[57.20546340942383,535.1884155273438,97.19498262913541,527.0465698242188]},{"page":12,"text":"Chakraborty, A.; Chakraborty, S.; Ganguly, T. Photoisomerization within a novel synthesized photoswitchable dyad: Experimental","rect":[57.20546340942383,547.570068359375,559.0130666456867,538.5414428710938]},{"page":12,"text":"and theoretical approaches. Ind. J. Phys. 2013, 87, 1113–1120. [CrossRef]","rect":[57.20546340942383,559.0459594726563,339.29833040745577,549.9725952148438]},{"page":12,"text":"Kawatsuki, N.; Matsushita, H.; Kondo, M.; Sasaki, T.; Ono, H. Photoinduced reorientation and polarization holography in a new","rect":[57.20546340942383,570.5587158203125,559.3953701591206,561.5300903320313]},{"page":12,"text":"photopolymer with 4-methoxy-N-benzylideneaniline side groups. APL Mater. 2013, 1, 022103. [CrossRef]","rect":[56.936588287353519,582.0535888671875,471.919241051987,573.007080078125]},{"page":12,"text":"Kawatsuki, N.; Matsushita, H.; Washio, T.; Kozuki, J.; Kondo, M.; Sasaki, T.; Ono, H. Photoinduced orientation of photoresponsive","rect":[57.20546340942383,593.530517578125,559.0132081754146,584.501953125]},{"page":12,"text":"polymers with N-benzylideneaniline derivative side groups. Macromolecules 2014, 47, 324–332. [CrossRef]","rect":[56.936588287353519,605.0432739257813,473.39781771214327,595.9519653320313]},{"page":12,"text":"Kawatsuki, N.; Miyake, K.; Kondo, M. Facile fabrication, photoinduced orientation, and birefringent pattern control of pho-","rect":[57.20546340942383,616.5380859375,560.5080434103851,607.4915771484375]},{"page":12,"text":"toalignable flms comprised of N-Benzylideneaniline side groups. ACS Macro Lett. 2015, 4, 764–768. [CrossRef]","rect":[57.20546340942383,628.0328979492188,493.62535677464327,618.9863891601563]},{"page":12,"text":"Kondo, M.; Kojima, D.; Ootsuki, N.; Kawatsuki, N. Photoinduced exfoliation of a polymeric N-benzylideneaniline liquid-","rect":[57.20546340942383,639.5277709960938,560.5042592306976,630.4812622070313]},{"page":12,"text":"crystalline composite based on a photoisomerization-triggered phase transition. Macromol. Chem. Phys. 2021, 222, 2100097.","rect":[57.20546340942383,651.0216064453125,560.5890216649029,641.9302978515625]},{"page":12,"text":"[CrossRef]","rect":[57.20546340942383,661.629638671875,98.66478548558072,653.4699096679688]},{"page":12,"text":"Kondo, M.; Uematsu, T.; Ootsuki, N.; Okai, D.; Adachi, H.; Kawatsuki, N. Photoinduced phase transition of N-benzylideneaniline","rect":[57.20546340942383,674.0112915039063,559.0171144254146,664.9647827148438]},{"page":12,"text":"liquid crystalline polymer and applications of photodismantlable adhesives. React. Funct. Polym. 2022, 174, 105247. [CrossRef]","rect":[57.20546340942383,685.506103515625,555.2126370480808,676.414794921875]},{"page":12,"text":"Hu, J.; Yu, H. Photoinduced solid-to-liquid transition of an N-benzylideneaniline derivative towards smart glass. New J. Chem.","rect":[57.20546340942383,697.0009155273438,560.1364402572015,687.9096069335938]},{"page":12,"text":"2024, 48, 4690–4698. [CrossRef]","rect":[57.20546340942383,707.6089477539063,179.86231050999479,699.44921875]},{"page":12,"text":"Lin, X.; Gablier, A.; Terentjev, E.M. Imine-based reactive mesogen and its corresponding exchangeable liquid crystal elastomer.","rect":[57.20546340942383,719.9906005859375,560.5873243208445,710.9619750976563]},{"page":12,"text":"Macromolecules 2022, 55, 821–830. [CrossRef]","rect":[57.20546340942383,730.5986938476563,231.55492220433073,722.3941650390625]},{"page":12,"text":"Dozov, I. On the spontaneous symmetry breaking in the mesophases of achiral banana-shaped molecules. Europhys. Lett. 2001, 56,","rect":[57.20546340942383,742.9802856445313,560.1369725347529,733.8889770507813]},{"page":12,"text":"247–253. [CrossRef]","rect":[57.20546340942383,753.5873413085938,135.05148897679167,745.4276123046875]},{"page":13,"text":"Materials 2024, 17, 3278","rect":[35.699440002441409,57.948081970214847,116.46322882991832,50.886077880859378]},{"page":13,"text":"13 of 14","rect":[532.09814453125,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":13,"text":"57.","rect":[35.699440002441409,96.91975402832031,46.902242638562388,90.57825469970703]},{"page":13,"text":"58.","rect":[35.69944763183594,131.4042510986328,46.902250267956919,125.06275177001953]},{"page":13,"text":"59.","rect":[35.69944763183594,154.3939971923828,46.902250267956919,148.052490234375]},{"page":13,"text":"60.","rect":[35.69944381713867,188.87745666503907,46.90224645325965,182.53594970703126]},{"page":13,"text":"61.","rect":[35.69944763183594,211.8671417236328,46.902250267956919,205.48086547851563]},{"page":13,"text":"62.","rect":[35.69944763183594,246.3516387939453,46.902250267956919,240.0101318359375]},{"page":13,"text":"63.","rect":[35.699440002441409,269.3403625488281,46.902242638562388,262.99884033203127]},{"page":13,"text":"64.","rect":[35.69941711425781,292.3299865722656,46.90221975037879,285.9436950683594]},{"page":13,"text":"65.","rect":[35.69944763183594,315.3196716308594,46.902250267956919,308.9781494140625]},{"page":13,"text":"66.","rect":[35.69944763183594,338.309326171875,46.902250267956919,331.9678039550781]},{"page":13,"text":"67.","rect":[35.69944381713867,361.2980651855469,46.90224645325965,354.95654296875]},{"page":13,"text":"68.","rect":[35.69944763183594,384.2876892089844,46.902250267956919,377.9461669921875]},{"page":13,"text":"69.","rect":[35.699462890625,407.2773742675781,46.90226552674598,400.93585205078127]},{"page":13,"text":"70.","rect":[35.699432373046878,430.26702880859377,46.90223500916785,423.9255065917969]},{"page":13,"text":"71.","rect":[35.69943618774414,453.10345458984377,46.90223882386512,446.86944580078127]},{"page":13,"text":"72.","rect":[35.69944763183594,464.5982666015625,46.902250267956919,458.4090270996094]},{"page":13,"text":"73.","rect":[35.69944381713867,487.7402038574219,46.90224645325965,481.398681640625]},{"page":13,"text":"74.","rect":[35.69947814941406,510.5776062011719,46.90228078553504,504.3435974121094]},{"page":13,"text":"75.","rect":[35.69944763183594,533.7195434570313,46.902250267956919,527.3780517578125]},{"page":13,"text":"76.","rect":[35.69944763183594,568.2030029296875,46.902250267956919,561.8615112304688]},{"page":13,"text":"77.","rect":[35.69944763183594,591.0404663085938,46.902250267956919,584.8511962890625]},{"page":13,"text":"78.","rect":[35.69944763183594,614.182373046875,46.902250267956919,607.8408813476563]},{"page":13,"text":"79.","rect":[35.69947814941406,637.1720581054688,46.90228078553504,630.83056640625]},{"page":13,"text":"80.","rect":[35.69941711425781,660.1607666015625,46.90221975037879,653.8192749023438]},{"page":13,"text":"81.","rect":[35.6994514465332,683.150390625,46.90225408265418,676.7640991210938]},{"page":13,"text":"82.","rect":[35.69943618774414,694.645263671875,46.90223882386512,688.3037719726563]},{"page":13,"text":"83.","rect":[35.69943618774414,729.1297607421875,46.90223882386512,722.7882690429688]},{"page":13,"text":"Cestari, M.; Diez-Berart, S.; Dunmur, D.A.; Ferrarini, A.; de La Fuente, M.R.; Jackson, D.J.; Lopez, D.O.; Luckhurst, G.R.; Perez-","rect":[57.20546340942383,99.25750732421875,560.501349893137,90.2468490600586]},{"page":13,"text":"Jubindo, M.A.; Richardson, R.M.; et al. Phase behavior and properties of the liquid-crystal dimer 1”,7”-bis(4-cyanobiphenyl-4’-yl)","rect":[57.05253219604492,110.77029418945313,559.9106262313635,101.72380828857422]},{"page":13,"text":"heptane: A twist-bend nematic liquid crystal. Phys. Rev. E Stat. Nonlin. Soft Matter Phys. 2011, 84, 031704. [CrossRef]","rect":[57.20546340942383,122.26510620117188,515.5380154660495,113.17383575439453]},{"page":13,"text":"Panov, V.P.; Balachandran, R.; Nagaraj, M.; Vij, J.K.; Tamba, M.G.; Kohlmeier, A.; Mehl, G.H. Microsecond linear optical response","rect":[57.20546340942383,133.75991821289063,559.0124155221496,124.7313461303711]},{"page":13,"text":"in the unusual nematic phase of achiral bimesogens. Appl. Phys. Lett. 2011, 99, 261903. [CrossRef]","rect":[57.20546340942383,145.25479125976563,441.1704922726901,136.16351318359376]},{"page":13,"text":"Chen, D.; Porada, J.H.; Hooper, J.B.; Klittnick, A.; Shen, Y.; Tuchband, M.R.; Korblova, E.; Bedrov, D.; Walba, D.M.; Glaser, M.A.;","rect":[57.20882797241211,156.73175048828126,560.1339931268436,147.72108459472657]},{"page":13,"text":"et al. Chiral heliconical ground state of nanoscale pitch in a nematic liquid crystal of achiral molecular dimers. Proc. Natl. Acad.","rect":[57.20546340942383,168.24337768554688,560.1396949018715,159.152099609375]},{"page":13,"text":"Sci. USA 2013, 110, 15931–15936. [CrossRef]","rect":[56.953582763671878,178.8515167236328,229.86151705296354,170.69175720214845]},{"page":13,"text":"Borshch, V.; Kim, Y.K.; Xiang, J.; Gao, M.; Jákli, A.; Panov, V.P.; Vij, J.K.; Imrie, C.T.; Tamba, M.G.; Mehl, G.H.; et al. Nematic","rect":[57.20546340942383,191.23312377929688,559.0173163440551,182.2045440673828]},{"page":13,"text":"twist-bend phase with nanoscale modulation of molecular orientation. Nat. Commun. 2013, 4, 2635. [CrossRef]","rect":[57.20546340942383,202.7100830078125,492.1374722531589,193.68150329589845]},{"page":13,"text":"Zhu, C.; Tuchband, M.R.; Young, A.; Shuai, M.; Scarbrough, A.; Walba, D.M.; Maclennan, J.E.; Wang, C.; Hexemer, A.; Clark,","rect":[57.20546340942383,214.22280883789063,560.1333942234967,205.19422912597657]},{"page":13,"text":"N.A. Resonant carbon K-edge soft X-ray scattering from lattice-free heliconical molecular ordering: Soft dilative elasticity of the","rect":[57.20546340942383,225.71762084960938,559.0203100843373,216.67112731933595]},{"page":13,"text":"twist-bend liquid crystal phase. Phys. Rev. Lett. 2016, 116, 147803. [CrossRef]","rect":[57.20546340942383,237.21249389648438,359.3734341672214,228.1212158203125]},{"page":13,"text":"Salili, S.M.; Kim, C.; Sprunt, S.; Gleeson, J.T.; Parri, O.; Jákli, A. Flow properties of a twist-bend nematic liquid crystal. RSC Adv.","rect":[57.20546340942383,248.70730590820313,560.1372713939198,239.61602783203126]},{"page":13,"text":"2014, 4, 57419–57423. [CrossRef]","rect":[57.20546340942383,259.3144226074219,184.34363375218229,251.15464782714845]},{"page":13,"text":"Challa, P.K.; Borshch, V.; Parri, O.; Imrie, C.T.; Sprunt, S.N.; Gleeson, J.T.; Lavrentovich, O.D.; Jákli, A. Twist-bend nematic liquid","rect":[57.20546340942383,271.67803955078127,559.0194808770737,262.6673889160156]},{"page":13,"text":"crystals in high magnetic felds. Phys. Rev. E Stat. Nonlin. Soft Matter Phys. 2014, 89, 060501. [CrossRef]","rect":[57.20546340942383,283.1907653808594,461.5950528195651,274.0994873046875]},{"page":13,"text":"Kumar, M.P.; Kula, P.; Dhara, S. Smecticlike rheology and pseudolayer compression elastic constant of a twist-bend nematic","rect":[57.20546340942383,294.6856384277344,559.0180487659301,285.63916015625]},{"page":13,"text":"liquid crystal. Phys. Rev. Mater. 2020, 4, 115601. [CrossRef]","rect":[57.20546340942383,306.1804504394531,287.3988247922214,297.08917236328127]},{"page":13,"text":"Merkel, K.; Loska, B.; Arakawa, Y.; Mehl, G.H.; Karcz, J.; Kocot, A. How do intermolecular interactions evolve at the nematic to","rect":[57.20546340942383,316.9319152832031,559.0184559977585,308.6467590332031]},{"page":13,"text":"twist–bent phase transition? Int. J. Mol. Sci. 2022, 23, 11018. [CrossRef]","rect":[57.20546340942383,329.1522216796875,335.6772061398776,320.078857421875]},{"page":13,"text":"Henderson, P.A.; Imrie, C.T. Methylene-linked liquid crystal dimers and the twist-bend nematic phase. Liq. Cryst. 2011, 38,","rect":[57.20546340942383,340.6650390625,560.1365680516217,331.636474609375]},{"page":13,"text":"1407–1414. [CrossRef]","rect":[56.75667190551758,351.27313232421877,143.56494722874479,343.1133728027344]},{"page":13,"text":"Mandle, R.J.; Davis, E.J.; Archbold, C.T.; Voll, C.C.; Andrews, J.L.; Cowling, S.J.; Goodby, J.W. Apolar bimesogens and the","rect":[57.20546340942383,363.6537170410156,559.0182376290946,354.6251525878906]},{"page":13,"text":"incidence of the twist–bend nematic phase. Chem. Eur. J. 2015, 21, 8158–8167. [CrossRef]","rect":[57.20546340942383,375.130615234375,404.4970913937839,366.0572509765625]},{"page":13,"text":"Jansze, S.M.; Martínez-Felipe, A.; Storey, J.M.; Marcelis, A.T.; Imrie, C.T. A twist-bend nematic phase driven by hydrogen bonding.","rect":[57.20546340942383,386.6433410644531,560.5877781988154,377.6147766113281]},{"page":13,"text":"Angew. Chem. Int. Ed. 2015, 54, 643–646. [CrossRef]","rect":[56.88261413574219,398.0755310058594,257.87772188694796,389.04693603515627]},{"page":13,"text":"Dawood, A.A.; Grossel, M.C.; Luckhurst, G.R.; Richardson, R.M.; Timimi, B.A.; Wells, N.J.; Yousif, Y.Z. On the twist-bend nematic","rect":[57.20546340942383,408.8896179199219,559.0130542373461,400.5865478515625]},{"page":13,"text":"phase formed directly from the isotropic phase. Liq. Cryst. 2016, 43, 2–12. [CrossRef]","rect":[56.936588287353519,421.12786865234377,389.4950772336276,412.0813903808594]},{"page":13,"text":"Arakawa, Y.; Komatsu, K.; Tsuji, H. Twist-bend nematic liquid crystals based on thioether linkage. New J. Chem. 2019, 43,","rect":[57.20546340942383,432.6227111816406,560.1365680516217,423.53143310546877]},{"page":13,"text":"6786–6793. [CrossRef]","rect":[57.20546340942383,443.2308044433594,144.01373873265104,435.071044921875]},{"page":13,"text":"Mandle, R.J. A ten-year perspective on twist-bend nematic materials. Molecules 2022, 27, 2689. [CrossRef] [PubMed]","rect":[57.20881652832031,455.61138916015627,513.6921597531589,446.5201110839844]},{"page":13,"text":"Tomczyk, W.; Longa, L. Role of molecular bend angle and biaxiality in the stabilization of the twist-bend nematic phase. Soft","rect":[57.20546340942383,467.106201171875,559.0164052267913,458.0149230957031]},{"page":13,"text":"Matter 2020, 16, 4350–4357. [CrossRef]","rect":[57.20546340942383,477.7143249511719,207.48349581272917,469.5545654296875]},{"page":13,"text":"Xiang, J.; Li, Y.; Li, Q.; Paterson, D.A.; Storey, J.M.; Imrie, C.T.; Lavrentovich, O.D. Electrically tunable selective refection of light","rect":[57.20546340942383,490.09588623046877,559.0126891396534,481.0494079589844]},{"page":13,"text":"from ultraviolet to visible and infrared by heliconical cholesterics. Adv. Mater. 2015, 27, 3014–3018. [CrossRef] [PubMed]","rect":[57.20546340942383,501.5906982421875,531.517873864487,492.4994201660156]},{"page":13,"text":"Liu, B.; Yuan, C.L.; Hu, H.L.; Wang, H.; Zhu, Y.W.; Sun, P.Z.; Li, Z.Y.; Zheng, Z.G.; Li, Q. Dynamically actuated soft heliconical","rect":[57.20546340942383,513.0855712890625,559.0197073125734,504.0390625]},{"page":13,"text":"architecture via frequency of electric felds. Nat. Commun. 2022, 13, 2712. [CrossRef]","rect":[57.20546340942383,524.5804443359375,387.7738858273776,515.533935546875]},{"page":13,"text":"Paterson, D.A.; Xiang, J.; Singh, G.; Walker, R.; Agra-Kooijman, D.M.; Martíne-Felipe, A.; Gao, M.; Storey, J.M.D.; Kumar, S.;","rect":[57.20546340942383,536.0751953125,560.1387653172467,527.0465698242188]},{"page":13,"text":"Lavrentovich, O.D.; et al. Reversible isothermal twist–bend nematic–nematic phase transition driven by the photoisomerization","rect":[57.20546340942383,547.570068359375,559.0192014058449,538.5414428710938]},{"page":13,"text":"of an azobenzene-based nonsymmetric liquid crystal dimer. J. Am. Chem. Soc. 2016, 138, 5283–5289. [CrossRef] [PubMed]","rect":[57.20546340942383,559.0639038085938,535.1751614621433,549.9725952148438]},{"page":13,"text":"Feng, C.; Feng, J.; Saha, R.; Arakawa, Y.; Gleeson, J.; Sprunt, S.; Zhu, C.; Jákli, A. Manipulation of the nanoscale heliconical","rect":[57.20546340942383,570.5587158203125,559.0157025167752,561.51220703125]},{"page":13,"text":"structure of a twist-bend nematic material with polarized light. Phys. Rev. Res. 2020, 2, 032004. [CrossRef]","rect":[57.20546340942383,582.0535888671875,473.4245816281589,572.9622802734375]},{"page":13,"text":"Arakawa, Y.; Komatsu, K.; Feng, J.; Zhu, C.; Tsuji, H. Distinct twist-bend nematic phase behaviors associated with the ester-linkage","rect":[57.20546340942383,593.5484619140625,559.0129640347896,584.5198364257813]},{"page":13,"text":"direction of thioether-linked liquid crystal dimers. Mater. Adv. 2021, 2, 261–272. [CrossRef]","rect":[57.20546340942383,605.0432739257813,414.1761990597995,595.9519653320313]},{"page":13,"text":"Tang, W.; Deng, M.; Kougo, J.; Ding, L.; Zhao, X.; Arakawa, Y.; Komatsu, K.; Tsuji, H.; Aya, S. Extreme modulation of liquid","rect":[57.20546340942383,616.5380859375,559.0182488806634,607.4915771484375]},{"page":13,"text":"crystal viscoelasticity via altering the ester bond direction. J. Mater. Chem. C 2021, 9, 9990–9996. [CrossRef]","rect":[57.20546340942383,628.0328979492188,476.3097744992526,618.9415893554688]},{"page":13,"text":"Aya, S.; Tang, W.; Kong, X.; Arakawa, Y.; Komatsu, K.; Tsuji, H. Nontrivial ultraslow dynamics under electric-feld in nematics of","rect":[57.20546340942383,639.5277709960938,559.0183767002476,630.4812622070313]},{"page":13,"text":"bent-shaped molecules. Phys. Chem. Chem. Phys. 2023, 25, 297–303. [CrossRef]","rect":[57.20546340942383,651.003662109375,364.7331143430026,641.9302978515625]},{"page":13,"text":"Zhou, J.; Tang, W.; Arakawa, Y.; Tsuji, H.; Aya, S. Viscoelastic properties of a thioether-based heliconical twist–bend nematogen.","rect":[57.20546340942383,662.5164184570313,560.5885043040761,653.4699096679688]},{"page":13,"text":"Phys. Chem. Chem. Phys. 2020, 22, 9593–9599. [CrossRef]","rect":[56.92759323120117,673.9485473632813,277.3430996945651,664.9199829101563]},{"page":13,"text":"Luckhurst, G.R. Liquid crystal dimers and oligomers: Experiment and theory. Macromol. Symp. 1995, 96, 1–26. [CrossRef]","rect":[57.208831787109378,685.506103515625,535.012502770737,676.414794921875]},{"page":13,"text":"Arakawa, Y.; Ishida, Y.; Tsuji, H. Ether- and thioether-linked naphthalene-based liquid-crystal dimers: Infuence of chalcogen","rect":[57.20546340942383,697.0009155273438,559.018160404644,687.9544067382813]},{"page":13,"text":"linkage and mesogenic-arm symmetry on the incidence and stability of the twist–bend nematic phase. Chem. Eur. J. 2020, 26,","rect":[57.20546340942383,708.4957275390625,560.1365680516217,699.4044189453125]},{"page":13,"text":"3767–3775. [CrossRef]","rect":[57.20546340942383,719.1038208007813,144.01373873265104,710.944091796875]},{"page":13,"text":"Mandle, R.J.; Goodby, J.W. Molecular fexibility and bend in semi-rigid liquid crystals: Implications for the heliconical nematic","rect":[57.20546340942383,731.4854736328125,559.0210666218389,722.43896484375]},{"page":13,"text":"ground state. Chem. Eur. J. 2019, 25, 14454–14459. [CrossRef]","rect":[57.20546340942383,742.9802856445313,295.5540371945651,733.8889770507813]},{"page":14,"text":"Materials 2024, 17, 3278","rect":[35.699440002441409,57.948081970214847,116.46322882991832,50.886077880859378]},{"page":14,"text":"14 of 14","rect":[532.09814453125,58.86416244506836,559.0166498504261,52.91679000854492]},{"page":14,"text":"84.","rect":[35.699440002441409,96.91975402832031,46.902242638562388,90.5334701538086]},{"page":14,"text":"85.","rect":[35.69943618774414,131.4042510986328,46.90223882386512,125.06275177001953]},{"page":14,"text":"86.","rect":[35.69943618774414,154.3939971923828,46.90223882386512,148.052490234375]},{"page":14,"text":"87.","rect":[35.69944763183594,177.38258361816407,46.902250267956919,171.04107666015626]},{"page":14,"text":"Arakawa, Y.; Komatsu, K.; Shiba, T.; Tsuji, H. Phase behaviors of classic liquid crystal dimers and trimers: Alternate induction","rect":[57.20546340942383,99.27542114257813,559.0119268338933,90.22893524169922]},{"page":14,"text":"of smectic and twist-bend nematic phases depending on spacer parity for liquid crystal trimers. J. Mol. Liq. 2021, 326, 115319.","rect":[57.20546340942383,110.77029418945313,560.5811481297467,101.67902374267578]},{"page":14,"text":"[CrossRef]","rect":[57.20546340942383,121.37837219238281,98.66478548558072,113.21862030029297]},{"page":14,"text":"Jaffé, H.H.; Yeh, S.J.; Gardner, R.W. The electronic spectra of azobenzene derivatives and their conjugate acids. J. Mol. Spectrosc.","rect":[57.20546340942383,133.75991821289063,560.1382555636182,124.66864776611328]},{"page":14,"text":"1958, 2, 120–136. [CrossRef]","rect":[56.75667190551758,144.36805725097657,165.97035799534636,136.2082977294922]},{"page":14,"text":"Knöpke, L.R.; Spannenberg, A.; Brückner, A.; Bentrup, U. The infuence of substituent effects on spectroscopic properties","rect":[57.20546340942383,156.74966430664063,559.0180193178941,147.7031707763672]},{"page":14,"text":"examined on benzylidene aniline-type imines. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2012, 95, 18–24. [CrossRef] [PubMed]","rect":[57.20546340942383,168.24337768554688,556.5485135129245,159.152099609375]},{"page":14,"text":"Shah, A.; Sannaikar, M.S.; Inamdar, S.R.; Duponchel, B.; Douali, R.; Singh, D.P. Photoluminescence modulation in the graphene","rect":[57.20546340942383,179.73825073242188,559.0170758421422,170.7096710205078]},{"page":14,"text":"oxide dispersed 4-n-octyl-4’-cyanobiphenyl molecular system. J. Lumin. 2020, 226, 117509. [CrossRef]","rect":[57.20546340942383,191.23312377929688,456.5854092648776,182.18663024902345]},{"page":14,"text":"Disclaimer/Publisher’s Note: The statements, opinions and data contained in all publications are solely those of the individual","rect":[35.699440002441409,217.25857543945313,559.0172283956814,208.2120819091797]},{"page":14,"text":"author(s) and contributor(s) and not of MDPI and/or the editor(s). MDPI and/or the editor(s) disclaim responsibility for any injury to","rect":[35.699440002441409,228.75234985351563,559.0207889848963,219.7058563232422]},{"page":14,"text":"people or property resulting from any ideas, methods, instructions or products referred to in the content.","rect":[35.43056869506836,240.24722290039063,449.71898458192177,231.2007293701172]}]}