Synthesis, characterisation, and effects of molecular structure on phase behaviour of 4-chloro-1,3-diazobenzene bent-core liquid crystals with high photosensitivity

References

• El-Bawab TS, editor. Optical Switching. Boston (MA): Springer US; 2006.
   Google Scholar
• De Sio L, Ricciardi L, Serak S, et al. Photo-sensitive liquid crystals for optically controlled diffraction gratings. J Mater Chem. 2012;22:6669.
   Web of Science ®Google Scholar
• Aronzon D, Levy EP, Collings PJ, et al. Trans–cis isomerization of an azoxybenzene liquid crystal. Liq Cryst. 2007;34:707–718.
   Web of Science ®Google Scholar
• Ikeda T, Tsutsumi O. Optical switching and image storage by means of azobenzene liquid-crystal films. Science. 1995;268:1873–1875.
   PubMed Web of Science ®Google Scholar
• Finkelmann H, Nishikawa E, Pereira GG, et al. A new opto-mechanical effect in solids. Phys Rev Lett. 2001;87:015501.
   PubMed Web of Science ®Google Scholar
• Reddy RA, Tschierske C. Bent-core liquid crystals: polar order, superstructural chirality and spontaneous desymmetrisation in soft matter systems. J Mater Chem. 2006;16:907–961.
   Web of Science ®Google Scholar
• Mahimwalla Z, Yager KG, Mamiya J, et al. Azobenzene photomechanics: prospects and potential applications. Polym Bull. 2012;69:967–1006.
   Web of Science ®Google Scholar
• Alaasar M. Azobenzene-containing bent-core liquid crystals: an overview. Liq Cryst. 2016;43:2208–2243.
   Web of Science ®Google Scholar
• Merino E, Ribagorda M. Control over molecular motion using the cis – trans photoisomerization of the azo group. Beilstein J Org Chem. 2012;8:1071–1090.
   PubMed Web of Science ®Google Scholar
• Aya S, Salamon P, Paterson DA, et al. Fast‐and‐Giant photorheological effect in a liquid crystal dimer. Adv Mater Interfaces. 2019;6:1802032.
   Web of Science ®Google Scholar
• Yoshioka J, Salamon P, Paterson DA, et al. Spherical-cap droplets of a photo-responsive bent liquid crystal dimer. Soft Matter. 2019;15:989–998.
   PubMed Web of Science ®Google Scholar
• Natansohn A, Rochon P. Photoinduced motions in azo-containing polymers. Chem Rev. 2002;102:4139–4176.
   PubMed Web of Science ®Google Scholar
• Camacho-Lopez M, Finkelmann H, Palffy-Muhoray P, et al. Fast liquid-crystal elastomer swims into the dark. Nat Mater. 2004;3:307–310.
   PubMed Web of Science ®Google Scholar
• Wang Y, Li Q. Light-driven chiral molecular switches or motors in liquid crystals. Adv Mater. 2012;24:1926–1945.
   PubMed Web of Science ®Google Scholar
• Garcia-Amorós J, Reig M, Castro MCR, et al. Molecular photo-oscillators based on highly accelerated heterocyclic azo dyes in nematic liquid crystals. Chem Commun. 2014;50:6704–6706.
   PubMed Web of Science ®Google Scholar
• Sunil BN, Srinatha MK, Shanker G, et al. Effective tuning of optical storage devices using photosensitive bent-core liquid crystals. J Mol Liq. 2020;304:112719.
   Web of Science ®Google Scholar
• Rahman ML, Asik J, Kumar S, et al. Liquid crystalline banana‐shaped monomers derived from 2,7‐naphthalene: synthesis and properties. Liq Cryst. 2008;35:1263–1270.
   Web of Science ®Google Scholar
• Lutfor MR, Hegde G, Kumar S, et al. Synthesis and characterization of bent-shaped azobenzene monomers: guest–host effects in liquid crystals with azo dyes for optical image storage devices. Opt Mater. 2009;32:176–183.
   Web of Science ®Google Scholar
• Nagaveni NG, Raghuvanshi P, Roy A, et al. Azo-functionalised achiral bent-core liquid crystalline materials: effect of presence of –N=N– linkage at different locations in the molecular architecture. Liq Cryst. 2013;40:1238–1254.
   Web of Science ®Google Scholar
• Ghosh S, Begum N, Turlapati S, et al. Ferroelectric-like switching in the nematic phase of four-ring bent-core liquid crystals. J Mater Chem C. 2014;2:425–431.
   Web of Science ®Google Scholar
• Paterson DA, Xiang J, Singh G, et al. Reversible isothermal twist–bend nematic–nematic phase transition driven by the photoisomerization of an azobenzene-based nonsymmetric liquid crystal dimer. J Am Chem Soc. 2016;138:5283–5289.
   PubMed Web of Science ®Google Scholar
• Alaasar M, Poppe S. Cybotactic nematic phases with wide ranges in photoresponsive polycatenars. Liq Cryst. 2020;47:939–949.
   Web of Science ®Google Scholar
• Paterson DA, Walker R, Abberley JP, et al. Azobenzene-based liquid crystal dimers and the twist-bend nematic phase. Liq Cryst. 2017;44:2060–2078.
   Google Scholar
• Abberley JP, Storey JMD, Imrie CT. Structure-property relationships in azobenzene-based twist-bend nematogens. Liq Cryst. 2019;46:2102–2114.
   Web of Science ®Google Scholar
• Alaasar M, Prehm M, Tschierske C. Influence of halogen substituent on the mesomorphic properties of five-ring banana-shaped molecules with azobenzene wings. Liq Cryst. 2013;40:656–668.
   Web of Science ®Google Scholar
• Horčic M, Kozmík V, Svoboda J, et al. Transformation from a rod-like to a hockey-stick-like and bent-shaped molecule in 3,4′-disubstituted azobenzene-based mesogens. J Mater Chem C. 2013;1:7560.
   Web of Science ®Google Scholar
• Gimeno N, Pintre I, Martínez-Abadía M, et al. Bent-core liquid crystal phases promoted by azo-containing molecules: from monomers to side-chain polymers. RSC Adv. 2014;4:19694–19702.
   Web of Science ®Google Scholar
• Dingemans TJ, Murthy NS, Samulski ET. Javelin-, Hockey Stick-, and boomerang-shaped liquid crystals. Structural variations on p -quinquephenyl †. J Phys Chem B. 2001;105:8845–8860.
   Web of Science ®Google Scholar
• Monika M, Prasad V, Nagaveni NG. Hockey stick-shaped azo compounds: effect of linkage groups and their direction of linking on mesomorphic properties. Liq Cryst. 2015;42:1490–1505.
   Web of Science ®Google Scholar
• Bobrovsky A, Shibaev V, Hamplová V, et al. Photo-optical properties of amorphous and crystalline films of azobenzene-containing photochromes with bent-shaped molecular structure. J Photochem Photobiol Chem. 2016;316:75–87.
   Web of Science ®Google Scholar
• Alaasar M, Prehm M, Tschierske C. Helical nano-crystallite (HNC) phases: chirality synchronization of achiral bent-core mesogens in a new type of dark conglomerates. Chem - Eur J. 2016;22:6583–6597.
   PubMed Web of Science ®Google Scholar
• Alaasar M, Prehm M, Brautzsch M, et al. 4-Methylresorcinol based bent-core liquid crystals with azobenzene wings – a new class of compounds with dark conglomerate phases. J Mater Chem C. 2014;2:5487–5501.
   Web of Science ®Google Scholar
• Zhang -X-X, Zhang J-H, Cong Y-H, et al. Synthesis, mesomorphic and photo-switching behaviours of novel azobenzene chiral liquid crystals containing (-)-menthyl. Liq Cryst. 2020;47:1345–1353.
   Web of Science ®Google Scholar
• Alaasar M, Prehm M, May K, et al. 4-cyanoresorcinol-based bent-core mesogens with azobenzene wings: emergence of sterically stabilized polar order in liquid crystalline phases. Adv Funct Mater. 2014;24:1703–1717.
   Web of Science ®Google Scholar
• Alaasar M, Prehm M, Brautzsch M, et al. Dark conglomerate phases of azobenzene derived bent-core mesogens – relationships between the molecular structure and mirror symmetry breaking in soft matter. Soft Matter. 2014;10:7285–7296.
   PubMed Web of Science ®Google Scholar
• Wang G, Zhang Z-Y, Wei B-M, et al. Synthesis of 4-alkylbiphenyls via cross-coupling reaction catalyzed by cupric chloride. Chin J Org Chem. 2008;28:538–541.
   Web of Science ®Google Scholar
• Kouwer PHJ, Jager WF, Mijs WJ, et al. Specific interactions in discotic liquid crystals. J Mater Chem. 2003;13:458–469.
   Web of Science ®Google Scholar
• Ma X, Ning R. A new synthetic process of P-alkylbenzoic acid. Spec Petrochem. 1999;1:25–28.
   Google Scholar
• Yi W, Cai C. Highly efficient dinitration of aromatic compounds in fluorous media using ytterbium perfluorooctanesulfonate and perfluorooctanesulfonic acid as catalysts. Synth Commun. 2006;36:2957–2961.
   Web of Science ®Google Scholar
• Meng G, Zheng M-L, Zheng A-Q, et al. The novel usage of thiourea nitrate in aryl nitration. Chin Chem Lett. 2014;25:87–89.
   Web of Science ®Google Scholar
• Hegde G, Rajkumar YA, Mei GS, et al. Photoisomerization behavior of photochromic amide-based azobenzene dyes exhibiting H-bonding effect: synthesis and characterization. Korean J Chem Eng. 2016;33:1480–1488.
   Web of Science ®Google Scholar
• Mathews M, Kang S, Kumar S, et al. Designing bent-core nematogens towards biaxial nematic liquid crystals. Liq Cryst. 2011;38:31–40.
   Web of Science ®Google Scholar
• Stroobants A, Lekkerkerker HNW, Odijk T. Effect of electrostatic interaction on the liquid crystal phase transition in solutions of rodlike polyelectrolytes. Macromolecules. 1986;19:2232–2238.
   Web of Science ®Google Scholar
• Meier G, Saupe A. Dielectric relaxation in nematic liquid crystals. Mol Cryst. 1966;1:515–525.
   Web of Science ®Google Scholar
• Vertogen G, de Jeu WH. Thermotropic liquid crystals, fundamentals. Heidelberg (BW): Springer Berlin Heidelberg; 1988.
   Google Scholar
• Gelbart WM. Molecular theory of nematic liquid crystals. J Phys Chem. 1982;86:4298–4307.
   Web of Science ®Google Scholar
• Singh S. Phase transitions in liquid crystals. Phys Rep. 2000;324:107–269.
   Google Scholar
• Israelachvili JN. 6 - Van der Waals Forces. In: Israelachvili JN, editor. Intermolecular Surf Forces Third Ed. San Diego: Academic Press; 2011. p. 107–132.
   Google Scholar
• Margenau H, Kestner N. Theory of intermolecular forces. 2nd ed. Elmsford (NY): Pergamon Press; 1969.
   Google Scholar
• Stone A. The theory of intermolecular forces. 2nd ed. Oxford: Oxford University Press; 2013.
   Google Scholar
• Hanwell MD, Curtis DE, Lonie DC, et al. Avogadro: an advanced semantic chemical editor, visualization, and analysis platform. J Cheminformatics. 2012;4:17.
   PubMed Web of Science ®Google Scholar
• Wang J, Wang W, Kollman PA, et al. Automatic atom type and bond type perception in molecular mechanical calculations. J Mol Graph Model. 2006;25:247–260.
   PubMed Web of Science ®Google Scholar
• Wang J, Wolf RM, Caldwell JW, et al. Development and testing of a general amber force field. J Comput Chem. 2004;25:1157–1174.
   PubMed Web of Science ®Google Scholar
• Avogadro: an open-source molecular builder and visualization tool. Version 1.2.0 [Internet]. Available from: http://avogadro.cc/
   Google Scholar
• Harada J, Ogawa K, Tomoda S. Molecular motion and conformational interconversion of azobenzenes in crystals as studied by X-ray diffraction. Acta Crystallogr B. 1997;53:662–672.
   Google Scholar
• Biswas N, Umapathy S. Density functional calculations of structures, vibrational frequencies, and normal modes of trans - and cis -azobenzene. J Phys Chem A. 1997;101:5555–5566.
   Web of Science ®Google Scholar
• Stewart JJP. Optimization of parameters for semiempirical methods VI: more modifications to the NDDO approximations and re-optimization of parameters. J Mol Model. 2013;19:1–32.
   PubMed Web of Science ®Google Scholar
• Baker J. An algorithm for the location of transition states. J Comput Chem. 1986;7:385–395.
   Web of Science ®Google Scholar
• Kanis DR, Ratner MA, Marks TJ. Design and construction of molecular assemblies with large second-order optical nonlinearities. Quantum chemical aspects. Chem Rev. 1994;94:195–242.
   Web of Science ®Google Scholar
• Ladanyi BM, Liang YQ. Interaction‐induced contributions to polarizability anisotropy relaxation in polar liquids. J Chem Phys. 1995;103:6325–6332.
   Web of Science ®Google Scholar
• Kurtz HA, Stewart JJP, Dieter KM. Calculation of the nonlinear optical properties of molecules. J Comput Chem. 1990;11:82–87.
   Web of Science ®Google Scholar
• Skaf MS, Vechi SM. Polarizability anisotropy relaxation in pure and aqueous dimethylsulfoxide. J Chem Phys. 2003;119:2181–2187.
   Web of Science ®Google Scholar
• Smith SM, Markevitch AN, Romanov DA, et al. Static and dynamic polarizabilities of conjugated molecules and their cations. J Phys Chem A. 2004;108:11063–11072.
   Web of Science ®Google Scholar
• Choi S-W, Izumi T, Hoshino Y, et al. Circular-polarization-induced enantiomeric excess in liquid crystals of an achiral, bent-shaped mesogen. Angew Chem Int Ed. 2006;45:1382–1385.
   PubMed Web of Science ®Google Scholar
• Vera F, Tejedor RM, Romero P, et al. Light-driven supramolecular chirality in propeller-like hydrogen-bonded complexes that show columnar mesomorphism. Angew Chem Int Ed. 2007;46:1873–1877.
   PubMed Web of Science ®Google Scholar
• Mathews M, Zola RS, Yang D, et al. Thermally, photochemically and electrically switchable reflection colors from self-organized chiral bent-core liquid crystals. J Mater Chem. 2011;21:2098–2103.
   Web of Science ®Google Scholar
• Senyuk B, Wonderly H, Mathews M, et al. Surface alignment, anchoring transitions, optical properties, and topological defects in the nematic phase of thermotropic bent-core liquid crystal A131. Phys Rev E. 2010;82:041711.
   Web of Science ®Google Scholar
• Fischer E. Calculation of photostationary states in systems A .dblarw. B when only A is known. J Phys Chem. 1967;71:3704–3706.
   Web of Science ®Google Scholar
• Victor JG, Torkelson JM. On measuring the distribution of local free volume in glassy polymers by photochromic and fluorescence techniques. Macromolecules. 1987;20:2241–2250.
   Web of Science ®Google Scholar
• Morishima Y, Tsuji M, Kamachi M, et al. Photochromic isomerization of azobenzene moieties compartmentalized in hydrophobic microdomains in a microphase structure of amphiphilic polyelectrolytes. Macromolecules. 1992;25:4406–4410.
   Web of Science ®Google Scholar
• Sasaki T, Ikeda T, Ichimura K. Photoisomerization and thermal isomerization behavior of azobenzene derivatives in liquid-crystalline polymer matrixes. Macromolecules. 1993;26:151–154.
   Web of Science ®Google Scholar
• Wang W, Wang M-Z. Effect of α-cyclodextrin on the photoisomerization of azobenzene functionalized hydroxypropyl methylcellulose in aqueous solution. Polym Bull. 2007;59:537–544.
   Web of Science ®Google Scholar
• Ya Q, Dong X-Z, Chen W-Q, et al. The synthesis of aminoazobenzenes and the effect of intermolecular hydrogen bonding on their photoisomerization. Dyes Pigm. 2008;79:159–165.
   Web of Science ®Google Scholar
• Fischer E. Temperature dependence of photoisomerization equilibria. Part I. Azobenzene and the azonaphthalenes. J Am Chem Soc. 1960;82:3249–3252.
   Web of Science ®Google Scholar
• Naito T, Horie K, Mita I. Photochemistry in polymer solids. 11. The effects of the size of reaction groups and the mode of photoisomerization on photochromic reactions in polycarbonate film. Macromolecules. 1991;24:2907–2911.
   Web of Science ®Google Scholar