Chloro-benzothiazole Schiff base ester liquid crystals: synthesis and mesomorphic ‎investigation

References

• Seed A. Synthesis of self-organizing mesogenic materials containing a sulfur-based five-membered heterocyclic core. Chem Soc Rev. 2007;36:2046–2069.
   PubMed Web of Science ®Google Scholar
• Karam N, Sultan M, Badri D, et al. Mesogenic materials incorporating 4H-1,2,4-triazol-3-thiol moiety: synthesis, characterization and liquid crystals study. J Mol Struct. 2018;1171:404–410.
   Web of Science ®Google Scholar
• Ghosh T, Lehmann M. Recent advances in heterocycle-based metal-free calamitics. J Mater Chem C. 2017;5:12308–12337.
   Web of Science ®Google Scholar
• Funahashi M, Hanna J. Photoconductive behavior in smectic a phase of 2-(4’-heptyloxyphenyl)-6-dodecylthiobenzothiazole. Jpn J Appl Phys. 1996;35:L703–L705.
   Web of Science ®Google Scholar
• Funahashi M, Hanna J. Fast hole transport in a new calamitic liquid crystal of 2-(4′-heptyloxyphenyl)-6-dodecylthiobenzothiazole. Phys Rev Lett. 1997;78:2184–2187.
   Web of Science ®Google Scholar
• Iino H, Hanna J. Liquid crystalline organic semiconductors for organic transistor applications. Polym J. 2017;49:23–30.
   Web of Science ®Google Scholar
• Yeap G, Abdul Rahim M, Lin C-M, et al. Synthesis and liquid crystalline studies of disc-shaped molecule on azo-bridged benzothiazole-phenyl ethers. J Mol Liq. 2016;223:734–740.
   Web of Science ®Google Scholar
• Gowda A, Roy A, Kumar S. Synthesis and mesomorphic properties of novel Schiff base liquid crystalline EDOT derivatives. J Mol Liq. 2017;225:840–847.
   Web of Science ®Google Scholar
• Gray G. Thermotropic liquid crystals. New York: Wiley; 1987.
   Google Scholar
• Ha S, Ng M, Subramaniam R, et al. Mesogenic azomethiane esters with different end groups: synthesis and thermotropic properties. Int J Phy Sci. 2010;5:1256–1262.
   Web of Science ®Google Scholar
• Collings P, Goodby J. Introduction to liquid crystals: chemistry and physics. 2nd ed. CRC Press, Taylor and Francis; 2019. DOI:10.1201/9781315098340.
   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
• Naoum M, Fahmi A, Abaza A, et al. Effect of exchange of terminal substituents on the mesophase behaviour of some azo/ester compounds. Liq Cryst. 2014;41:1559–1568.
   Web of Science ®Google Scholar
• Hagar M, Ahmed H, Saad G. Mesophase stability of new Schiff base ester liquid crystals with different polar substituents. Liq Cryst. 2018;45:1324–1332‏.
   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
• Arakawa Y, Inui S, Igawa K, et al. Alkylthio- and alkyl-substituted asymmetric diphenyldiacetylene-based liquid crystals: phase transition, mesophase and single-crystal structures, and birefringence. Liq Cryst. 2019;46:1621–1630.
   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. DOI:10.1039/C4RA15300F
   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 behaviour. Liq Cryst. 2018;45:821–830.
   Web of Science ®Google Scholar
• Cruickshank E, Strachan GJ, Storey JM, et al. Chalcogen bonding and liquid crystallinity: understanding the anomalous behaviour of the 4′-(alkylthio)[1,1′-biphenyl]-4-carbonitriles (nSCB). J Mol Liq. 2022;346(346):117094. DOI:10.1016/j.molliq.2021.117094
   Web of Science ®Google Scholar
• Arakawa Y, Komatsu K, Ishida Y, et al. Thioether-Linked azobenzene-based liquid crystal dimers exhibiting the twist-bend nematic phase over a wide temperature range. Liq Cryst. 2021;48:641–652.
   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
• Arakawa Y, Ishida Y, Sasaki Y, et al. Alkylthio-Based asymmetric liquid crystals: unravelling the substituent effects and intercalated cybotactic nematic and smectic phases. Mater Adv. 2022;3:3218–3228.
   Web of Science ®Google Scholar
• Cruickshank E, Anderson K, Storey JMD, et al. Helical phases assembled from achiral molecules: twist-bend nematic and helical filamentary B-4 phases formed by mesogenic dimers. J Mol Liq. 2022;346:118180.
   Web of Science ®Google Scholar
• Zong X, Fang Z, Wu C. 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
• Ha S, Koh T, Lin H, et al. Heterocyclic benzothiazole-based liquid crystals: synthesis and mesomorphic properties. Liq Cryst. 2009;36:917–925.
   Web of Science ®Google Scholar
• Iwan A, Gorecki L, Pociecha D. Liquid crystalline properties of new unsymmetrical compounds with benzothiazole core detected by TG/DSC-POM-XRD. J Therm Anal Calorim. 2012;110:43–49.
   Web of Science ®Google Scholar
• Ha S, Koh T, Ong S, et al. Synthesis and mesomorphic behavior of benzothiazole-based liquid crystals having terminal methoxyl group. Chin Chem Lett. 2009;20:1449–1452.
   Web of Science ®Google Scholar
• Koh T, Ha S, Lee T, et al. Synthesis and mesomorphic evaluation of new calamitic liquid crystals containing benzothiazole core. Chin Chem Lett. 2011;22:619–622.
   Web of Science ®Google Scholar
• Abberley JP, Killah R, Walker R, et al. Heliconical smectic phases formed by achiral molecules. Nature Commun. 2018;9:228.
   PubMed Web of Science ®Google Scholar
• Salamonczyk M, Vaupotic N, Pociecha D, et al. Multi-Level chirality in liquid crystals formed by achiral molecules. Nature Commun. 2019;10:1922.
   PubMed Web of Science ®Google Scholar
• Ha S, Koh T-M, Yeap G-Y, et al. Mesogenic Schiff base esters with benzothiazole core: synthesis and phase transition studies. Phase Transit. 2010;83:195–204.
   Web of Science ®Google Scholar
• Porta E, Verdaguer I, Perez C, et al. Repositioning Salirasib as a new antimalarial agent. Med Chem Commun. 2019;10:1599–1605.
   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
• 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(2):205–211. DOI:10.1080/02678290500450584
   Web of Science ®Google Scholar
• Ha S, Koh T, Win Y, et al. Phase transition behaviours of calamitic liquid crystals comprising phenylbenzothiazole core. Liq Cryst. 2013;40:1016–1023.
   Web of Science ®Google Scholar
• Nafee S, Hagar M, Ahmed H, et al. The synthesis of new ‎thermal stable Schiff base/ester liquid crystals: a computational, mesomorphic, and ‎optical study. Molecules. 2019;24:3032.
   PubMed Web of Science ®Google Scholar
• Nafee S, Hagar M, Ahmed H, et al. New two rings Schiff base liquid crystals; ball mill synthesis, mesomorphic, Hammett and DFT studies. J Mol Liq. 2020;299:112161.
   Web of Science ®Google Scholar
• Ahmed N, Saad G, Ahmed H, et al. New wide-stability four-ring azo/ester/Schiff base liquid crystals: synthesis, mesomorphic, photophysical, and DFT approaches. RSC Adv. 2020;10:9643–9656.
   PubMed Web of Science ®Google Scholar
• Gray G. Molecular structure and the properties of liquid crystals. 2nd ed. London (UK): Academic Press; 1969.
   Google Scholar
• Prajapati A, Bonde N. Mesogenic benzothiazole derivatives with methoxy substituents. J Chem Sci. 2006;118:203–210.
   Web of Science ®Google Scholar
• Goodby J, Collings P, Kato T, et al. Handbook of liquid crystals. 2nd ed. Vol. 8. Germany: Wiley; 2014
   Google Scholar
• Blinov L. Structure and properties of liquid crystals. London: Springer; 2011.
   Google Scholar
• Prajapati A, Bonde N, Pate H. Mesogenic Schiff’s base ester with chloroethyl tail. Phase Transit. 2005;78:507–513.
   Web of Science ®Google Scholar
• Ha S, Foo K, Yeap G, et al. Mesogenic Schiff base ethers with heterocyclic benzothiazole core: synthesis and phase transition studies. Inter Conf Chem Biolog Environ Eng. 2012;43:149–153.
   Google Scholar
• Ha S, Foo K, Lin HC, et al. Mesomorphic behavior of new benzothiazole liquid crystals having Schiff base linker and terminal methyl group. Chin Chem Lett. 2012;23:761–764.
   Web of Science ®Google Scholar
• Fattepur R, Fattepur K, Ayachit N. Estimation of entropy and enthalpy of a nematic liquid crystal using time domain reflectometry studies. J Therm Anal Calorim. 2012;109:457–460.
   Web of Science ®Google Scholar
• Kumar S. Liquid crystals: experimental study of physical properties and phase transitions. UK: Cambridge University Press; 2001.
   Google Scholar
• Yeap GY, Lee HC, Mahmood WA, et al. Synthesis, thermal and optical behaviour of non-symmetric liquid crystal dimers alpha-(4-benzylidene-substituted-aniline-4 ‘-oxy)-omega- pentyl-4-(4’-phenyl)benzoateoxy hexane. Phase Transitions. 2011;84:29–37.
   Web of Science ®Google Scholar
• Yeap GY, Osman F, Imrie CT. Non-symmetric chiral liquid crystal dimers. Preparation and characterisation of the (S)-(benzylidene-4 ‘-substitutedaniline)-2’‘-methylbutyl-4’’‘-(4’’’’-phenyloxy)-benzoateoxy)hexanoates. J Mol Struct. 2016;1111:118–125.
   Web of Science ®Google Scholar
• Tschierske C. Mirror symmetry breaking in liquids and liquid crystals. Liq Cryst. 2018;45:2221–2252.
   Web of Science ®Google Scholar
• Imrie C, Henderson P, Yeap G. Liquid crystal oligomers: going beyond dimers. Liq Cryst. 2009;36:755–777.
   Web of Science ®Google Scholar
• Chiellini E, Galli G. Liquid crystals and their mesophases: an introduction in structure and ‎transport properties in ‎organized polymeric materials. In: Chiellini E, Giordano M Leporini D, editors. Singapore: World Scientific; 1998.
   Google Scholar
• Ha S. New mesogenic Schiff base esters with polar chloro substituent: synthesis, thermotropic properties and X-ray diffraction studies. Am J Appl Sci. 2010;7:214–220.
   Google Scholar
• Attard GS, Date RW, Imrie CT, et al. Nonsymmetrical dimeric liquid-crystals - the preparation and properties of the alpha-(4-cyanobiphenyl-4’-yloxy)-omega-(4-n-alkylanilinebenzylidene-4’-o xy)alkanes. Liq Cryst. 1994;16:529–581.
   Web of Science ®Google Scholar
• Byron J, Lacey D, Wilson C. Properties of the liquid crystals formed by certain 4”-n-alkoxyphenyl biphenyl-4-carboxylates. Mol Cryst Liq Cryst. 1979;51:265–272.
   Web of Science ®Google Scholar
• Ha S, Lee T. Synthesis and mesomorphic properties of new fluorinated Schiff base liquid crystals. Int Sch Res Notices. 2014;904657. DOI:10.1155/2014/904657
   Google Scholar
• Imrie CT, 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
• Thaker B, Patel B, Dhimmar Y. Mesomorphic studies of novel azomesogens having a benzothiazole core: synthesis and characterisation. Liq Cryst. 2013;40:237–248.
   Web of Science ®Google Scholar
• Ha S, Lee T, Lee S, et al. Schiff base liquid crystals with terminal iodo group: synthesis and thermotropic properties. Sci Res Essays. 2011;6:5025–5035.
   Google Scholar
• Walker R, Pociecha D, Storey JMD, et al. Remarkable smectic phase behaviour in odd-membered liquid crystal dimers: the CT6O.M series. J Mater Chem C. 2021;9:5167–5173‎.
   Web of Science ®Google Scholar
• Dierking I. Textures of liquid crystals. Weinheim: Wiley Verlag; 2003.
   Google Scholar