New azo-benzothiazole based liquid crystals: synthesis and study of the effect of lateral ‎substituents on their liquid crystalline behaviour

References

• Singh S, Dunmur DA. Liquid crystals: fundamentals. Singapore: World Scientific; 2002. DOI:10.1142/4369.
   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
• Yu YB, He WL, Jiang ZM, et al. The effects of azo-oxadiazole-based bent-shaped molecules on the temperature range and the light-responsive performance of blue phase liquid crystal. Liq Cryst. 2019;46:1024–1034.
   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
• 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 dinner. J Am Chem Soc. 2016;138:5283–5289.
   PubMed Web of Science ®Google Scholar
• Cruickshank E, Salamonczyk M, Pociecha D, et al. Sulfur-linked cyanobiphenyl-based liquid crystal dimers and the twist-bend nematic phase. Liq Cryst. 2019;46:1595–1609.
   Web of Science ®Google Scholar
• Zong XN, Fang ZM, Wu CC. Synthesis and mesomorphic properties of a series of dimers derived from thioether-terminated and cholesteryl. Liq Cryst. 2018;45:1844–1853.
   Web of Science ®Google Scholar
• Arakawa Y, Inui S, Igawa K, et al. Alkylthio- and alkyl-substituted asymmetric diphenyldiacetylene-based liquid crystals: phase transitions, mesophase and single-crystal structures, and birefringence. Liq Cryst. 2019;46:1621–1630.
   Web of Science ®Google Scholar
• Arakawa Y, Inui S, Tsuji H. Novel diphenylacetylene-based room-temperature liquid crystalline molecules with alkylthio groups, and investigation of the role for terminal alkyl chains in mesogenic incidence and tendency. Liq Cryst. 2018;45:811–820.
   Web of Science ®Google Scholar
• Arakawa Y, Sasaki Y, Haraguchi N, et al. Synthesis, phase transitions andbirefringence of novel liquid crystalline 1,4-phenylene bis(4-alkylthio benzoates) and insightsinto the cybotactic nematic behaviour. Liq Cryst. 2018;45:821–830.
   Web of Science ®Google Scholar
• Ahmed HA, Hagar M, Alhaddad OA. Mesomorphic and geometrical orientation study of the relative position of fluorine atom in some thermotropic liquid crystal systems. Liq Cryst. 2020;47:404–413.
   Web of Science ®Google Scholar
• Saad GR, Ahmed NHS, Fahmi AA, et al. Influence of lateral methyl and terminal substituents on the mesophase behaviour of four rings azo-ester liquid crystal compounds. Liq Cryst. 2019;46:1285–1297.
   Web of Science ®Google Scholar
• Saad GR, Ahmed NHS, Fahmi AA, et al. Effect of orientation of lateral methyl substituent on the thermal behaviour of the mesophase in binary systems of 4-substituted phenyl 4ʹ-(4”-alkoxy phenylazo) benzoates. Liq Cryst. 2018;45:1177–1185.
   Web of Science ®Google Scholar
• Mahmoud NE, Saad GR, Fahmi AA, et al. Effect of including extra phenylazo moiety on the mesophase behaviour of three-ring azo/ester molecules. Liq Cryst. 2018;45:1711–1722.
   Web of Science ®Google Scholar
• Thaker B, Kanojiya J. Mesomorphic properties of liquid crystalline compounds with biphenyl moiety containing azo-ester, azo-cinnamate central linkages and different terminal group. Liq Cryst. 2011;38:1035–1055.
   Web of Science ®Google Scholar
• Varia M, Kumar S, Prajapati A. H-shaped azoester-oxymethylene containing twin liquid crystalline compounds. Liq Cryst. 2012;39:365–371.
   Web of Science ®Google Scholar
• Yeap G, Lee H, Mahmood W, et al. Synthesis, thermal and optical behaviour of non-symmetric liquid crystal dimers α-(4-benzylidene-substituted-aniline-4′-oxy)-ω-[pentyl-4-(4′-phenyl)benzoateoxy]hexane. Phase Transit. 2011;84:29–37.
   Web of Science ®Google Scholar
• Lai L, Lin H. Synthesis and mesogenic properties of azo-dye liquid crystals. Liq Cryst. 2000;27:707–709.
   Web of Science ®Google Scholar
• Yeap G, Osman F, Imrie C. Non-symmetric dimers: effects of varying the mesogenic linking unit and terminal substituent. Liq Cryst. 2015;42:543–554.
   Web of Science ®Google Scholar
• Karim M, Sheikh M, Yahya R, et al. Synthesis of polymerizable liquid crystalline monomers and their side chain liquid crystalline polymers bearing azo-ester linked benzothiazole mesogen. Colloid Polym Sci. 2015;293:1923–1935.
   Web of Science ®Google Scholar
• Belmar J, Parra M, Zuanaiga C, et al. New liquid crystals containing the benzothiazol unit: amides and azo compounds. Liq Cryst. 1999;26:389–396.
   Web of Science ®Google Scholar
• Naoum M, Fahmi A, Abaza A, et al. The effect of orientation of the lateral methyl substituent on the mesophase behaviour of 4-alkoxyphenylazo aryl benzoates. Liq Cryst. 2016;43:1831–1845.
   Web of Science ®Google Scholar
• Dave J, Bhatt H. Synthesis of liquid crystals with lateral methyl group and study of their mesomorphic properties. Mol Cryst Liq Cryst. 2012;562:1–9.
   Web of Science ®Google Scholar
• Jain B, Patel R. Synthesis and mesomorphism of novel chalconyl esters with a lateral nitro group. Mol Cryst Liq Cryst. 2016;637:1–9.
   Web of Science ®Google Scholar
• Ahmed N, Saad G, Naoum M. Effect of lateral bromo substituent on the phase behavior of four-ring azo/ester/azo liquid crystalline materials. Liq Cryst. 2019;46:1631–1642.
   Web of Science ®Google Scholar
• Prajapati A, Varia M. Azomesogens with polar chloro, nitro and phenolic –OH substituents. Liq Cryst. 2008;35:1271–1277.
   Web of Science ®Google Scholar
• Gray GW. liquid crystals and molecular structure-nematics and cholesteries. In: Luckhurst GR, Gray GW, editors. The molecular physics of liquid crystals. London, UK: Academic Press; 1979. p. 285–316.
   Google Scholar
• Goodby JW. Nano-objects-sculpting and shape in molecular material design (The Pierre Gilles de Gennes ILCS prize lecture). Liq Cryst. 2019;46:1901–1924.
   Web of Science ®Google Scholar
• Imrie C, Taylor L. The preparation and properties of low molar mass liquid crystals possessing lateral alkyl chains. Liq Cryst. 1989;6:1–10.
   Web of Science ®Google Scholar
• Weissflog W, Demus D. Compounds with lateral long‐chain substituents-a new molecule structure concept for thermotropic liquid crystals. Cryst Res Technol. 1983;18:K21.
   Web of Science ®Google Scholar
• Weissflog W, Demus D. Thermotropic liquid crystalline compounds with lateral long‐chain substituents (II): synthesis and liquid crystalline properties of 1,4‐Bis [4‐substituted‐ benzoyloxy]‐2‐n‐alkylbenzenes. Cryst Res Technol. 1984;19:K55.
   Web of Science ®Google Scholar
• Weissplog W, Diele S, Demus D. Thermotropic liquid crystalline compounds with lateral long-chain substituents part VIII: liquid crystalline 2.4 and 3,4-di-alkyloxy-benzylidene-amino derivates of 4-cyanobiphenyl and) 4-cyanophenyl benzoate. Mater Chem Phys. 1986;15:475–482.
   Web of Science ®Google Scholar
• Attard G, Imrie C. Trimeric liquid crystals containing lateral alkyl chains. Liq Cryst. 1989;6:387–390.
   Web of Science ®Google Scholar
• Imrie C. Laterally substituted dimeric liquid crystals. Liq Cryst. 1989;6:391–396.
   Web of Science ®Google Scholar
• Chang C, Chien S, Hsu C, et al. Synthesis of laterally substituted α‐methylstilbene‐tolane liquid crystals. Liq Cryst. 2008;35:1–9.
   Web of Science ®Google Scholar
• Al-Hamdani U, Gassim T, Radhy H. Synthesis and characterization of azo compounds and study of the effect of substituents on their liquid crystalline behavior. Molecules. 2010;15:5620–5628.
   PubMed Web of Science ®Google Scholar
• Patel D, Prajapati H, Doshi A. Mesomorphism dependence on lateral substitution of functional groups and their position in series: 4(4′-n-alkoxy benzoyloxy)-3-chloro phenyl azo-2″-methoxy benzenes. Mol Cryst Liq Cryst. 2016;624:51–58.
   Web of Science ®Google Scholar
• Yousif Y, Al-hamdani A. Liquid-crystalline behaviour of some bis(4-alkyloxyphenyl) thiazolo [5,4-d] dithiazoles. Liq Cryst. 1993;15:451–460.
   Web of Science ®Google Scholar
• Ha S-T, Koh T-M, Lin H-C, et al. Heterocyclic benzothiazole-based liquid crystals: synthesis and mesomorphic properties. Liq Cryst. 2009;36:917–925.
   Web of Science ®Google Scholar
• Chakraborty BB, Anwar S, Das S, et al. Aggregation dependent fluorescence switching in benzothiazole derivative based H-bonded mesogen. Liq Cryst. 2018;45:1644–1653.
   Web of Science ®Google Scholar
• Vogel AI. Textbook of practical organic chemistry. 5th ed. New York: John Wiley; 1989.
   Google Scholar
• Al-Hamdani U. Mesomorphic properties of an homologous series of thioalkyl-terminated azomesogens. Int J Mol Sci. 2011;12:3182–3190.
   PubMed Web of Science ®Google Scholar
• Al-Hamdani U, Al-Ibrahim A, Abbo H, et al. Synthesis and mesomorphic properties of new methylene-linked linear symmetrical liquid crystal dimers. Mol Cryst Liq Cryst. 2015;607:13–22.
   Web of Science ®Google Scholar
• Al-Hamdani U, Abbo H, Shaheeb E, et al. Symmetrical and asymmetrical liquid crystal dimers: synthesis, characterisation and mesomorphic behaviour. Liq Cryst. 2019;46:2291–2300.
   Web of Science ®Google Scholar
• Gray GW. Molecular structure and the properties of liquid crystals. 2nd ed. London, UK: Academic Press; 1969. p. 235.
   Google Scholar
• Tschierske C. Mirror symmetry breaking in liquids and liquid crystals. Liq Cryst. 2018;45:2221–2252.
   Web of Science ®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
• Prajapati A, Bonde N. Mesogenic schiff’s base esters with a methoxyethyl tail. Mol Cryst Liq Cryst. 2006;461:15–28.
   Web of Science ®Google Scholar
• Senthil S, Kamalraj VR, Wu SL. Synthesis and characterization of ferroelectric liquid crystal dimers containing thioester and carboxylate linking groups in the inner side of the molecule. J Mol Str. 2008;886(1–3):175–182.
   Web of Science ®Google Scholar
• Ahmed N, Saad G, Naoum M. Effect of position of the lateral fluoro substituent on the mesophase behaviour of aryl 4-alkoxyphenylazo benzoates in pure and binary mixtures. Liq Cryst. 2018;45:1487–1497.
   Web of Science ®Google Scholar
• Kumar S. Liquid crystals: experimental study of physical properties and phase transition. UK: Cambridge University Press; 2001.
   Google Scholar
• Ha S-T, Koh T-M, Yeap G-Y, et al. Synthesis and mesomorphic properties of 6-Methoxy- and 6-Ethoxy-2-(2-Hydroxy-4-alkanoyloxybenzylidenamino) benzothiazoles. Mol Cryst Liq Cryst. 2010;528:10–22.
   Web of Science ®Google Scholar
• Chan TN, Lu ZB, Yam WS, et al. Non-symmetric liquid crystal dimers containing an isoflavone moiety. Liq Cryst. 2012;39:393–402.
   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
• 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
• Martinez-Felipe A, Cook AG, Wallage MJ, et al. Hydrogen bonding and liquid crystallinity of low molar mass and polymeric mesogens containing benzoic acids: a variable temperature Fourier transform infrared spectroscopic study. Phase Transitions. 2014;87:1191–1210.
   Web of Science ®Google Scholar
• Martinez-Felipe A, Cook AG, Abberley JP, et al. An FT-IR spectroscopic study of the role of hydrogen bonding in the formation of liquid crystallinity for mixtures containing bipyridines and 4-pentoxybenzoic acid. RSC Adv. 2016;6:108164–108179.
   Web of Science ®Google Scholar
• Yeap G-Y, Ha S-T, Lim P-L, et al. ‎Synthesis and mesomorphic ‎properties of Schiff base esters ortho-hydroxy-para-alkyloxybenzylidene-para-substituted anilines. ‎Mol ryst Liq Cryst. 2004;423:73–84.
   Web of Science ®Google Scholar
• Demus D, Richter L. Textures of liquid crystals. Weinheim: Wiley; 1978.
   Google Scholar