Improved mesomorphic behaviour and large birefringence of fluorinated liquid crystals containing ethynyl and 1-methyl-1H-benzimidazole moieties

References

• Geelhaar T, Griesar K, Reckmann B. 125 years of liquid crystals—a scientific revolution in the home. Angew Chem Int Ed. 2013;52(34):8798–8809.
   PubMed Web of Science ®Google Scholar
• Luo Z, Peng F, Chen H, et al. Fast-response liquid crystals for high image quality wearable displays. Opt Mater Express. 2015;5(3):603–610.
   Web of Science ®Google Scholar
• Kirsch P, Bremer M. Nematic liquid crystals for active matrix displays: molecular design and synthesis. Angew Chem Int Ed. 2000;39(23):4216–4235.
   PubMed Web of Science ®Google Scholar
• Gray GW, Hird M, Toyne KJ. The synthesis and transition temperatures of some lateral monofluoro-substituted 4,4″- dialkyl- and 4,4″-alkoxyalkyl- 1, 1′: 4′,1″-terphenyls. Mol Cryst Liq Cryst. 1991;195(1):221–237.
   Web of Science ®Google Scholar
• Chan LKM, Gray GW, Lacey D, et al. Synthesis and liquid crystal behaviour of further 4,4″-disubstituted 2ʹ-fluoro-1,1ʹ:4ʹ,1”-terphenyls. Mol Cryst Liq Cryst. 1988;158(2):209–240.
   Web of Science ®Google Scholar
• Chan LKM, Gray GW, Lacey D. Syntheis and evaluation of some 4,4ʹ-disunbstituted lateral fluoro-1,1ʹ,4ʹ,1ʹ- terphenyls. Mol Cryst Liq Cryst. 1985;123(1):185–204.
   Web of Science ®Google Scholar
• Devadiga D, Ahipa TN. Recent synthetic advances in pyridine-based thermotropic mesogens. RSC Adv. 2019;9:23161–23228.
   PubMed Web of Science ®Google Scholar
• Kirsch P. Fluorine in liquid crystal design for display applications. J Fluorine Chem. 2015;177:29–36.
   Web of Science ®Google Scholar
• Weng Q, Duna L, Chen P, et al. Synthesis and mesomorphic properties of benzoxazole derivatives with lateral multifluoro substituents. Liq Cryst. 2019;46(1):59–66.
   Web of Science ®Google Scholar
• Ahmed NHS, Saad GR, Naoum MM. 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(10):1487–1497.
   Web of Science ®Google Scholar
• Pytlarczyk M, Herman J, Harmata P, et al. The influence of the dialkylphenyltolane’s difluorosubstitution on mesomorphic and dielectric properties. Liq Cryst. 2018;45(10):1460–1469.
   Web of Science ®Google Scholar
• Goossens K, Wellens S, Van Hecke K, et al. T-shaped Ionic liquid crystals based on the imidazolium motif: exploring substitution of the C-2 imidazolium carbon atom. Chem Eur J. 2011;17(15):4291–4306.
   PubMed Web of Science ®Google Scholar
• Cheng X, Bai X, Jing S, et al. Self-assembly of imidazolium-based rodlike ionic liquid crystals: transition from lamellar to micellar organization. Chem Eur J. 2010;16(15):4588–4601.
   PubMed Web of Science ®Google Scholar
• Goossens K, Nockemann P, Driesen K, et al. Imidazolium ionic liquid crystals with pendant mesogenic groups. Chem Mater. 2008;20(1):157–168.
   Web of Science ®Google Scholar
• Roddecha S, Anthamatten M. Synthesis and thermotropic behaviour of imidazole-terminated liquid crystals. Liq Cryst. 2010;37(4):389–397.
   Web of Science ®Google Scholar
• Kadkin ON, Tae J, Kim SY, et al. Liquid crystal phases generated by supramolecular self-assembly of biforked amphiphilic imidazoles. Liq Cryst. 2009;36(12):1337–1347.
   Web of Science ®Google Scholar
• Seo SH, Tew GN, Chang JY. Lyotropic columnar liquid crystals based on polycatenar 1H-imidazole amphiphiles and their assembly into bundles at the surface of silicon. Soft Matter. 2006;2(10):886–891.
   PubMed Web of Science ®Google Scholar
• Yeap CW, Haque RA, Yam WS, et al. Asymmetric N-heterocyclic carbene benzimidazolium salts and their silver(I) complexes: potential as ionic liquid crystals. Liq Cryst. 2018;45(8):1210–1222.
   Web of Science ®Google Scholar
• Zhang L, Chen X, Zhao F, et al. Synthesis and mesomorphic properties of 2-(4′-alkoxybiphenyl-4-yl)-1H-benzimidazole derivatives. Liq Cryst. 2013;40(3):396–410.
   Web of Science ®Google Scholar
• Duan L, Shi D, Chen P, et al. Preparation and characterisation of laterally monofluorinated mesogenic benzimidazole-based compounds. Liq Cryst. 2017;44(11):1678–1685.
   Web of Science ®Google Scholar
• Ren L, Duan L, Weng Q, et al. Preparation and mesomorphic properties of 1-methyl-1H-benzimidazole-based compounds. Liq Cryst. 2019;46(1):131–137.
   Web of Science ®Google Scholar
• Dąbrowski R, Kula P, Herman J. High birefringence liquid crystals. Crystals. 2013;3(3):443–482.
   Web of Science ®Google Scholar
• Liao Y-M, Chen H-L, Hsu C-S, et al. Synthesis and mesomorphic properties of super high birefringence isothiocyanato bistolane liquid crystals. Liq Cryst. 2007;34(4):507–517.
   Web of Science ®Google Scholar
• Lin P-T, Wu S-T, Chang C-Y, et al. UV stability of high birefringence liquid crystals. Mol Cryst Liq Cryst. 2004;411(1):185–204.
   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(3):393–402.
   Web of Science ®Google Scholar
• Henderson PA, Niemeyer O, Imrie CT. Methylenelinked liquid crystal dimers. Liq Cryst. 2001;28(3):463–472.
   Web of Science ®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):1–10.
   Web of Science ®Google Scholar
• Lee H-C, Lu Z, Henderson PA, et al. Cholesteryl-based liquid crystal dimers containing a sulfur–sulfur link in the flexible spacer. Liq Cryst. 2012;39(2):259–268.
   Web of Science ®Google Scholar
• Dang J, Du S, Ren L, et al. Preparation and properties of 1-methyl-1H-benzimidazole-based mesogenic compounds incorporating ethynyl moiety. Liq Cryst. TLCT-2019-0336; Submitted. DOI: 10.1080/02678292.2019.1710780.
   Web of Science ®Google Scholar
• Shi D, Hu K, Chen P, et al. Improved nematic mesophase stability of benzoxazole-liquid crystals via modification of inter-ring twist angle of biphenyl unit. Liq Cryst. 2016;43(10):1397–1407.
   Web of Science ®Google Scholar
• Duan L, Shi D, Chen P, et al. Preparation and properties of laterally multifluorinated benzoxazole-based nematic mesogens. Liq Cryst. 2017;44(11):1686–1694.
   Web of Science ®Google Scholar
• Wang L, Lin X, Liang X, et al. Large birefringence liquid crystal material in terahertz range. Opt Mater Express. 2012;2(10):1314–1319.
   Web of Science ®Google Scholar
• Si G, Zhao Y, Leong E, et al. Liquid-crystal-enabled active plasmonics: a review. Materials. 2014;7(2):1296–1317.
   PubMed Web of Science ®Google Scholar
• Hu K, Weng Q, Chen R, et al. Benzoxazole-terminated liquid crystals with high birefringence and large dielectric anisotropy. Liq Cryst. TLCT-2019-0299; Submitted. DOI:10.1080/02678292.2019.1710777.
   Web of Science ®Google Scholar
• Hu M, An Z, Li J, et al. Tolane liquid crystals bearing fluorinated terminal group and their mid-wave infrared properties. Liq Cryst. 2014;41(12):1696–1702.
   Web of Science ®Google Scholar
• Frisch MJ, Trucks G, Schlegel HB, et al. Gaussian 09 revision a.1. Gaussian inc; 2009.
   Google Scholar
• Chen R, An Z, Wang W, et al. Lateral substituent effects on UV stability of high-birefringence liquid crystals with the diaryl-diacetylene core: DFT/TD-DFT study. Liq Cryst. 2017;44(10):1515–1524.
   Web of Science ®Google Scholar