Synthesis and mesomorphic properties of a series of dimers derived from thioether-terminated and cholesteryl

References

• Itahara T. Effects of combining of different flexible spacers in liquid crystal trimers and tetramers ontransition properties. Liq Cryst. 2010;37:1157–1163.
   Web of Science ®Google Scholar
• Yelamaggad CV, Mathews M, Fujita T, et al. Mesogenic unsymmetric dimers containing cholesteryl ester and tolane moieties. Liq Cryst. 2003;30:1079–1087.
   Web of Science ®Google Scholar
• Imrie CT. Editorial: 30 years of liquid crystals. Liq Cryst. 2016;43:1.
   Web of Science ®Google Scholar
• Imrie CT, Lu Z, Picken SJ, et al. Oligomeric rod-disc nematic liquid crystals. Chem Commun. 2007;1245–1247.
   PubMed Web of Science ®Google Scholar
• Ciastek S, Szymanska K, Kaszynski P, et al. Smectic behaviour of methyl 4-alkoxybenzoates with a partially fluorinated alkyl chain. Liq Cryst. 2018;45:11–21.
   Web of Science ®Google Scholar
• Chen HR, Zhang RL, Gao HF, et al. Synthesis, self-assembly, metal binding properties of triazole azobenzene based polycatenar dyes through click chemistry. Dyes Pigm. 2018;149:512–520.
   Web of Science ®Google Scholar
• Wang X, He WL, Yang Z, et al. The effects of asymmetric bent-shaped compounds on the temperature range and electro-optical performances of liquid crystalline blue phases. RSC Adv. 2016;112:110750–110757.
   Web of Science ®Google Scholar
• Balamurugan R, Zhang YS, Fitriyani S, et al. Click chemistry-assisted, bis-cholesteryl-appended, isosorbide-based, dual-responsive organogelators and their self-assemblies. Soft Matter. 2016;12:5214–5223.
   PubMed Web of Science ®Google Scholar
• Sankarranarayanan K, Kavitha C, Mohan MLNM. Chemical and optical characterization of linear hydrogen bonded thermotropic liquid crystal dimers. Optik. 2017;143:42–58.
   Web of Science ®Google Scholar
• So BK, Kim WJ, Lee SM, et al. Novel bent-shaped liquid crystalline compounds: III.Synthesis of Schiff base liquid crystal dimmers. Dyes Pigm. 2007;75:619–623.
   Web of Science ®Google Scholar
• Sharma VS, Vekariya RH, Sharma AS, et al. Synthesis and mesomorphic properties of new chalconyl-ester based liquid crystals: the effect of tail group. Mol Cryst Liq Cryst. 2017;652:10–22.
   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
• Varshney SK, Nagayama H, Prasad V, et al. Room temperature columnar phase: influence of 2-ethylhexane peripheral chain on the mesomorphism polyalkynylbenzene-based disc-shaped molecules. Liq Cryst. 2011;38:1321–1329.
   Web of Science ®Google Scholar
• Lee SK, Li X, Kang S, et al. Electric-field-induced transition between ferro- and antiferroelectric ground states observed in the B7 phase of a bent-shaped molecule with alkylthio tails. J Mater Chem. 2010;20:3615–3618.
   Web of Science ®Google Scholar
• Heppke G, Parghi DD, Sawade H. Novel sulphur-containing banana-shaped liquid crystal molecules. Liq Cryst. 2000;27:313–320.
   Web of Science ®Google Scholar
• Minch BA, Xia W, Donley CL, et al. Octakis (2-benzyloxyethylsulfanyl) copper (II) phthalocyanine: a new liquid crystalline discotic material with benzyl-terminated, thioether-linked side chains. Chem Mater. 2005;17:1618–1627.
   Web of Science ®Google Scholar
• Arakawa Y, Kang S, Tsuji H, et al. Development of novel bistolane-based liquid crystalline molecules with an alkylsulfanyl group for highly birefringent materials. RSC Adv. 2016;6:16568–16574.
   Web of Science ®Google Scholar
• Arakawa Y, Sasaki Y, Haraguchi N, et al. Synthesis, phase transitions and birefringence of novel liquid crystalline 1,4-phenylene bis (4-alkylthio benzoates) and insights into the cybotactic nematic behavior. Liq Cryst. 2018;45:821–830.
   Web of Science ®Google Scholar
• Wang W, Sun X, Wu W, et al. Photoinduced deformation of crosslinked liquid-crystalline polymer film oriented by a highly aligned carbon nanotube sheet. Angew Chem Int Ed. 2012;51:4644–4647.
   PubMed Web of Science ®Google Scholar
• Isogai H, Tadano K, Yano S. Liquid crystallinity in polythioethers of 1,4-bis(mercaptomethyl)benzene (MB) and 4,4 ‘-bis(mercaptomethyl)biphenyl (MBP) with alpha,omega-dibromo-n-alkanes and polythioesters of MB and MBP with n-alkanedioyl dichlorides. Liq Cryst. 2008;35:689–694.
   Web of Science ®Google Scholar
• Nishiyama I, Yamamoto J, Goodby JW, et al. Effect of introducing thioether linkages on the molecular organization of chiral twin liquid crystals. Liq Cryst. 2004;31:1495–1502.
   Web of Science ®Google Scholar
• Gowda A, Roy A, Kumar S. Synthesis and mesomorphic properties of novel Schiff base liquid crystalline EDOT derivatives. J Mole Liq. 2017;225:840–847.
   Web of Science ®Google Scholar
• Yu HB, Huang ZG, Yin BZ, et al. Chiral dimesogenic compounds having cholesterol and 4- (trans-4-n-hexylcyclohexyl) benzoic acid moieties. Mater Lett. 2008;62:3284–3287.
   Web of Science ®Google Scholar
• Paul MK, Kalita G, Laskar AR, et al. Synthesis and mesomorphism of new chiral imines and copper (II) complexes. J Mole Struct. 2013;1039:219–266.
   Web of Science ®Google Scholar
• Guo HY, Yang FF, Liu WW, et al. Novel supramolecular liquid crystals: synthesis and mesomorphic properties of calyx [4] arene-cholesterol derivatives. Tetrahedron Lett. 2015;56:866–870.
   Web of Science ®Google Scholar
• Han CY, Guo HY, Lai JB, et al. Calix [4] resorcinarene-cholesterol columnar liquid crystals: synthesis, mesomorphism and the influence of spacers on liquid crystalline behaviors. J Mole Liq. 2017;231:220–224.
   Web of Science ®Google Scholar
• Yeap GY, Hng TC, Yeap SY, et al. Why do nonsymmetric dimers intercalate? The synthesis and characterization of the α - (4-benzylidene-substituted-aniline-4′-oxy) - ω - (2-methylbutyl-4′-(4″-phenyl) benzoateoxy) alkanes. Liq Cryst. 2009;36:1431–1441.
   Web of Science ®Google Scholar
• Yeap GY, Osman F, Imrie CT. Non-symmetric dimers: effectsof varying the mesogenic linking unit and terminal substituent. Liq Cryst. 2015;42:543–554.
   Web of Science ®Google Scholar
• Imrie CT, Henderson PA. Liquid crystal dimers and oligomers. Curr Opin Colloid Interface Sci. 2002;7:298–311.
   Web of Science ®Google Scholar
• Yelamaggad CV, Nagamani SA, Hiremath US, et al. Unsymmetrical trimesogens exhibiting the undulated twist grain boundary (UTGBC*) mesophase. Liq Cryst. 2001;28:1581–1583.
   Web of Science ®Google Scholar
• Yelamaggad CV, Prabhu R, Rao DSS, et al. The first examples of supramolecular discotic C-3h tris (N-salicylideneamine) s featuring inter- and intra-molecular H-bonding: synthesis and characterization. Tetrahedron Lett. 2010;57:4579–4583.
   Web of Science ®Google Scholar
• Yeap GY, Ha ST, Lim PL, et al. Synthesis, physical and mesomorphic properties of Schiff’s base esters containing ortho-, meta- and para-substituents in benzylidene-4 ‘-alkanoyloxyanilines. Liq Cryst. 2006;33:205–211.
   Web of Science ®Google Scholar
• Yelamaggad CV, Prabhu R, Shanker G, et al. Optically active, mesogenic lanthanide complexes: design, synthesis and characterization. Liq Cryst. 2009;36:247–255.
   Web of Science ®Google Scholar
• Yeap GY, Nakata M, Takanishi Y, et al. Smectic A and smectic C materials: partially deuteriated chiral liquid crystals (S)-(-)-2-methylbutyl 4-(4-(d (13))-hexyloxyphenyl) benzoate and (S)-(-)-2-methylbutyl 4-(4-(d (17))-octyloxyphenyl) benzoate. Liq Cryst. 2000;27:1437–1443.
   Web of Science ®Google Scholar
• Wu CC. Synthesis and characterization of a novel series of unsymmetric dimesogenic compounds containing cholesteryl ester and nitroazobenzene moieties. Mater Lett. 2007;61:1380–1383.
   Web of Science ®Google Scholar
• Donaldson T, Henderson PA, Achard MF, et al. Non-symmetric chiral liquid crystal trimers. Liq Cryst. 2011;38:1331–1339.
   Web of Science ®Google Scholar
• Donaldson T, Staesche H, Lu ZB, et al. Symmetric and non-symmetric chiral liquid crystal dimers. Liq Cryst. 2010;37:1097–1110.
   Web of Science ®Google Scholar
• Lee HC, Lu Z, Henderson PA, et al. Cholesteryl-based liquid crystal dimers containing a sulfur-sulfur link in the flexible spacer. Liq Cryst. 2012;39:259–268.
   Web of Science ®Google Scholar
• Ooi YH, Yeap GY. λ-Shaped liquid crystal trimers with dual terminal cholesteryl moieties: synthesis and concomitant of N*, SmA and cholesteric glassy phases. Liq Cryst. 2018;45:204–218.
   Web of Science ®Google Scholar
• Osman F, Yeap GY, Maeta N, et al. Phase transitional behaviour of S-shaped oligomers incorporating biphenylene and cholesterol entities. Liq Cryst. 2017;44:822–832.
   Web of Science ®Google Scholar
• Gorecka E, Vaupotic N, Zep A, et al. A twist-bend nematic (N-TB) phase of chiral materials. Angew Chem Intl Ed. 2015;54:10155–10159.
   PubMed Web of Science ®Google Scholar
• Walker R, Pociecha D, Abberley JP, et al. Spontaneous chirality through mixing achiral components: a twist-bend nematic phase driven by hydrogen-bonding between unlike components. Chem Commun. 2018;54:3383–3386.
   PubMed Web of Science ®Google Scholar
• Abberley JP, Jansze SM, Walker R, et al. Structure-property relationships in twist-bend nematogens: the influence of terminal groups. Liq Cryst. 2017;44:68–83.
   Web of Science ®Google Scholar
• Paterson DA, Abberley JP, Harrison WT, et al. Cyanobiphenyl-based liquid crystal dimers and the twist-bend nematic phase. Liq Cryst. 2017;44:127–146.
   Web of Science ®Google Scholar
• Dawood AA, Grossel MC, Luckhurst GR, et al. Twist-bend nematics, liquid crystal dimers, structure-property relations. Liq Cryst. 2017;44:106–126.
   Web of Science ®Google Scholar
• Archbold CT, Andrews JL, Mandle RJ, et al. Effect of the linking unit on the twist-bend nematic phase in liquid crystal dimers: a comparative study of two homologous series of methylene- and ether-linked dimers. Liq Cryst. 2017;44:84–92.
   Web of Science ®Google Scholar
• Ivsic T, Baumeister U, Dokli I, et al. Sensitivity of the N-TB phase formation to the molecular structure of imino-linked dimers. Liq Cryst. 2017;44:93–105.
   Web of Science ®Google Scholar
• Lu Z, Henderson PA, Paterson BJA, et al. Liquid crystal dimers and the twist-bend nematic phase. The preparation and characterisation of the alpha, omega-bis (4-cyanobiphenyl-4ʹ-yl) alkanedioates. Liq Cryst. 2014;41:471–483.
   Web of Science ®Google Scholar
• Paterson DA, Gao M, Kim YK, et al. Understanding the twist-bend nematic phase: the characterisation of 1- (4-cyanobiphenyl-4ʹ-yloxy) - 6 - (4-cyanobiphenyl-4ʹ-yl) hexane (CB6OCB) and comparison with CB7CB. Soft Matter. 2016;12:6827–6840.
   PubMed Web of Science ®Google Scholar
• Abberley JP, Killah R, Walker R, et al. Heliconical smectic phases formed by achiral molecules. Nat Commun. 2018;9:228.
   PubMed 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.
   Web of Science ®Google Scholar
• Wu CC. Synthesis and liquid crystalline properties of a series of cholesterol-based dimesogenic compounds. Liq Cryst. 2007;34:283–288.
   Web of Science ®Google Scholar
• Arakawa Y, Sasaki Y, Igawa K, et al. Hydrogen bonding liquid crystalline benzoic acids with alkylthio groups: phase transition behavior and insights into cybotactic nematic phase. New J Chem. 2017;41:6514–6522.
   Web of Science ®Google Scholar
• Varshney SK, Nagayama H, Prasad V, et al. Room temperature columnar phase: influence of 2-ethylhexane peripheral chain on the mesomorphism of polyalkynylbenzene-based disc-shaped molecules. Liq Cryst. 2011;38:1321–1329.
   Web of Science ®Google Scholar
• Hu JS, Zhang BY, Liu LM, et al. Synthesis, structures, and properties of side-chain cholesteric liquid-crystalline polysiloxanes. J Appl Poly Sci. 2003;89:3944–3950.
   Web of Science ®Google Scholar
• Foo KL, Ha ST, Lin CM, et al. Synthesis, characterization and mesomorphic properties of new symmetrical dimer liquid crystals derived from benzothiazole. Karbala Inter J Mod Sci. 2015;1:152–158.
   Google Scholar
• Imrie CT, Henderson PA, Yeap GY. Liquid crystal oligomers: going beyond dimers. Liq Cryst. 2009;36:755–777.
   Web of Science ®Google Scholar
• Henderson PA, Inkster RT, Seddon JM, et al. Highly non-linear liquid crystal tetramers. J Mater Chem. 2001;11:2722–2731.
   Web of Science ®Google Scholar
• Chan T-N, Lu Z, Yam W-S, et al. Non-symmetric liquid crystal dimers containing an isoflavone moiety. Liq Cryst. 2012;39:393–402.
   Web of Science ®Google Scholar
• Imrie CT, Stewart D, Remy C, et al. Liquid crystal tetramers. J Mater Chem. 1999;9:2321–2325.
   Web of Science ®Google Scholar
• Osman F, Yeap GY, Nagashima A, et al. Structure property and mesomorphic behaviour of S-shaped liquid crystal oligomers possessing two azobenzene moieties. Liq Cryst. 2016;43:1283–1292.
   Web of Science ®Google Scholar
• Wolska JM, Pociecha D, Mieczkowski J, et al. Double gyroid structures made of asymmetric dimmers. J Liq Cryst. 2016;43:235–240.
   Web of Science ®Google Scholar
• Imrie CT, Henderson PA. Liquid crystal dimers and higher oligomers: between monomers and polymers. Chem Soc Rev. 2007;36:2096–2124.
   PubMed Web of Science ®Google Scholar
• Imrie CT. Non-symmetric liquid crystal dimers: how to make molecules intercalate. Liq Cryst. 2006;33:1449–1454.
   Web of Science ®Google Scholar
• Arakawa Y, Kang S, Watanabe J, et al. Assembly of thioether-containing rod-like liquid crystalline materials assisted by hydrogen-bonding terminal carboxyl groups. RSC Adv. 2015;5:8056–8062.
   Web of Science ®Google Scholar
• Arakawa Y, Kang SM, Tsuji H, et al. The design of liquid crystalline bistolane-based materials with extremely high birefringence. RSC Adv. 2016;6:92845–92851.
   Web of Science ®Google Scholar
• Dewar MJS, Schroeder JP. p-Alkoxy-and p-carbalkoxybenzoates of diphenols. A new series of liquid crystalline compounds. J Org Chem. 1965;30:2296–2300.
   Web of Science ®Google Scholar
• Dewar MJS, Goldberg RS. Role of p-phenylene groups in nematic liquid crystals. J Am Chem Soc. 1970;92:1582–1586.
   Web of Science ®Google Scholar
• Dewar MJS, Goldberg RS. Effects of central and terminal groups on nematic mesophase stability. J Org Chem. 1970;35:2711–2715.
   Web of Science ®Google Scholar
• Zhang LP, Wang M, Wang L, et al. Polymeric infrared reflective thin films with ultra-broad bandwidth. Liq Cryst. 2016;43:750–757.
   Web of Science ®Google Scholar
• Wu XJ, Cao H, Guo RW, et al. Effect of cholesteric liquid crystalline elastomer with binaphthalene crosslinkings on thermal and optical properties of a liquid crystal that show smectic A-cholesteric phase transition. Polym Adv Tech. 2013;24:228–235.
   Web of Science ®Google Scholar
• Zurowska M, Czerwinski M. The new high tilt mixtures with antiferroelectric phase at a broad temperature range and a long helical picth. Liq Cryst. 2017;44:1044–1049.
   Web of Science ®Google Scholar
• Sarman S, Wang YL, Laaksonen A. Thermomechanical coupling in coarse grained cholesteric liquid crystal model systems with pitches of realistic length. Phys Chem Chem Phys. 2016;18:16822–16829.
   PubMed Web of Science ®Google Scholar
• Govindaiah TN, Sreepad HR, Nagappa X. Optical and thermal characterization of binary mixtures of liquid crystals. Mol Cryst Liq Cryst. 2013;574:9–18.
   Web of Science ®Google Scholar
• Gvozdovskyy I. ‘Blue phases’ of highly chiral thermotropic liquid crystals with a wide range of near-room temperature. Liq Cryst. 2015;42:1391–1404.
   Web of Science ®Google Scholar
• Hu JS, Zhang B, Yao D, et al. Cholesteric liquid crystalline thermosets: synthesis, structure and properties of ChLCTs/precusor polymers. Liq Cryst. 2004;31:393–400.
   Web of Science ®Google Scholar
• Wu CC, Yang SS. Synthesis and characterization of linear-shaped and bent-shaped dicholesteryl liquid crystalline compounds. Mod Chem Ind. 2008;28:51–53.
   Google Scholar
• Hu JS, Zhang BY, Jia YG, et al. Side-chain cholesteric liquid crystalline elastomers derived from a mesogenic cross-linking agent. Macromolecules. 2003;36:2849–2858.
   Web of Science ®Google Scholar
• Liu YJ, Wang FR, Sun WM, et al. Tunable capability of dye-doped cholesteric liquid crystal lasers. Acta Phys Sin. 2013;62:7.
   Google Scholar
• Yelamaggad CV, Shanker G, Hiremath US, et al. Cholesterol-based nonsymmetric liquid crystal dimers: an overview. J Mater Chem. 2008;18:2927–2949.
   Web of Science ®Google Scholar
• Chien CC, Liu JH. Optical behaviors of cholesteric liquid-crystalline polyester composites with various chiral photochromic dopants. Langmuir. 2015;31:13410–13419.
   PubMed Web of Science ®Google Scholar