Synthesis of novel (-)-menthol-based azobenzene chiral liquid crystals and effect of terminal alkyl chains on mesomorphic behaviour

References

• 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
• Lintuvuori JS, Yu G, Walker M, et al. Emergent chirality in achiral liquid crystals: insights from molecular simulation models of the behaviour of bent-core mesogens. Liq Cryst. 2018;45:1996–2009.
   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
• Wang L, Urbas AM, Li Q. Nature-inspired emerging chiral liquid crystal nanostructures: from molecular self-assembly to DNA mesophase and nanocolloids. Adv Mater. 2018;30:1801335.
   Web of Science ®Google Scholar
• Goodby JW. Chirality in liquid crystals. J Mater Chem. 1991;1:307–318.
   Web of Science ®Google Scholar
• Yoshizawa A. Molecular design of flexible liquid crystal oligomers stabilising the chiral frustrated phases. Liq Cryst. 2017;44:1877–1893.
   Web of Science ®Google Scholar
• Yoshizawa A, Kato H. Coexistence of nematic and chiral nematic phases of an achiral liquid crystal trimer possessing an octafluorobiphenyl unit. Liq Cryst. 2018;45:1443–1450.
   Web of Science ®Google Scholar
• Kim Y, Tamaoki N. Asymmetric dimers of chiral azobenzene dopants exhibiting unusual helical twisting power upon photoswitching in cholesteric liquid crystals. Acs Appl Mater Interface. 2016;8:4918–4926.
   PubMed Web of Science ®Google Scholar
• Donaldson T, Henderson PA, Achard MF, et al. Chiral liquid crystal tetramers. J Mater Chem. 2011;21:10935–10941.
   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
• Huang CC, Hsu CC, Chen LW, et al. The effect of position of (S)-2-octyloxy tail on the formation of frustrated blue phase and antiferroelectric phase in Schiff base liquid crystals. Soft Matter. 2014;10:9343–9351.
   PubMed Web of Science ®Google Scholar
• Novotna V, Fekete L, Hamplova V, et al. Effect of lactate group in the chiral chain of new compounds exhibiting short-pitch cholesteric or TGBA phase. Liq Cryst. 2018;45:1155–1163.
   Web of Science ®Google Scholar
• Wu SL, Chen TS. Synthesis and frustrated phases of chiral liquid crystals derived from (R)-3-alkoxy-2-methylpropionic acids. Liq Cryst. 2005;32:63–68.
   Web of Science ®Google Scholar
• Parra ML, Saavedra CG, Hidalgo PI, et al. Novel chiral liquid crystals based on amides and azo compounds derived from 2-amino-1,3,4-thiadiazoles: synthesis and mesomorphic properties. Liq Cryst. 2008;35:55–64.
   Web of Science ®Google Scholar
• Rokunohe J, Yoshizawa A. An unusual phase sequence of iso liq-blue phase-smectic A observed for novel binaphthyl mesogenic derivatives. J Mater Chem. 2005;15:275–279.
   Web of Science ®Google Scholar
• Wu SL, Yen PC, Hsieh WJ. TGB(A) phase in a series of swallow tailed chiral liquid crystals. Liq Cryst. 1998;24:741–746.
   Web of Science ®Google Scholar
• Ely F, Conte G, Merlo AA, et al. A new synthetic approach based on (-)-menthone for chiral liquid crystals. Liq Cryst. 2004;31:1413–1425.
   Web of Science ®Google Scholar
• Ho WM, Wong HNC, Navailles L, et al. Chiral liquid crystalline compounds from D-(+)-glucose. Tetrahedron. 1995;51:7373–7388.
   Web of Science ®Google Scholar
• Cowling SJ, Hall AW, Goodby JW. Effect of terminal functional group size on ferroelectric and antiferroelectric properties of liquid crystals. Liq Cryst. 2005;32:1483–1498.
   Web of Science ®Google Scholar
• Donaldson T, Henderson PA, Achard MF, et al. Non-symmetric chiral liquid crystal trimers. Liq Cryst. 2011;38(10):1331–1339.
   Web of Science ®Google Scholar
• Ge SJ, Zhao TP, Wang M, et al. A homeotropic main-chain tolane-type liquid crystal elastomer film exhibiting high anisotropic thermal conductivity. Soft Matter. 2017;13:5463–5468.
   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
• 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
• Yelamaggad CV, Bonde NL, Achalkumar AS, et al. Frustrated liquid crystals: synthesis and mesomorphic behavior of unsymmetrical dimers possessing chiral and fluorescent entities. Chem Mater. 2007;19:2463–2472.
   Web of Science ®Google Scholar
• Zhang CB, Jin LY, Yin BZ, et al. Synthesis and properties of non-symmetric liquid crystal dimers containing a cholesteryl moiety. Liq Cryst. 2008;35:39–44.
   Web of Science ®Google Scholar
• Marcelis ATM, Koudijs A, Karczmarzyk Z, et al. Cholesterol-containing liquid crystal dimers with ether linkages between the spacer and mesogenic units. Liq Cryst. 2003;30:1357–1364.
   Web of Science ®Google Scholar
• Abraham S, Mallia VA, Ratheesh KV, et al. Reversible thermal and photochemical switching of liquid crystalline phases and luminescence in diphenylbutadiene-based mesogenic dimers. J Am Chem Soc. 2006;128:7692–7698.
   PubMed Web of Science ®Google Scholar
• Marcelis ATM, Koudijs A, Sudholter EJR. Dimer liquid crystals with bent mesogenic units. Liq Cryst. 2000;27:1515–1523.
   Web of Science ®Google Scholar
• He WL, Li M, Liu SQ, et al. Synthesis of chiral azobenzene derivatives and the performance in photochemical control of blue phase liquid crystal. Liq Cryst. 2018;45:370–380.
   Web of Science ®Google Scholar
• Chen XW, Wang L, Li CY, et al. Light-controllable reflection wavelength of blue phase liquid crystals doped with azobenzene-dimers. Chem Commun. 2013;49:10097–10099.
   PubMed Web of Science ®Google Scholar
• He WL, Gu H, Zhao P, et al. Synthesis and mesophase behaviour of branched azobenzene-based supramolecular hydrogenbonded liquid crystals. Liq Cryst. 2017;44:593–602.
   Web of Science ®Google Scholar
• Zheng ZG, Yuan CL, Hu W, et al. Light-patterned crystallographic direction of a self-organized 3D soft photonic crystal. Adv Mater. 2017;29:1703165.
   Web of Science ®Google Scholar
• Luo CC, Jia YG, Sun BF, et al. The effect of chain length in terminal groups on the mesomorphic behavior of novel (-)-menthol-based chiral liquid crystal compounds with a blue phase. New J Chem. 2017;41:3677–3686.
   Web of Science ®Google Scholar
• Jia YG, Luo CC, Zhu ZX, et al. Synthesis and properties of new (-)-menthol-derived chiral liquid crystal compounds with alkyl or alkoxy terminal groups. Liq Cryst. 2017;44:526–537.
   Web of Science ®Google Scholar
• Luo CC, Sun SL, Wang YS, et al. The effect of various functional groups on mesophase behavior and optical property of blue phase liquid crystal compounds based on (-)-menthol. J Mol Liq. 2108;269:755–765.
   Google Scholar
• Luo CC, Meng QL, Wang JW, et al. Effect of spacer length on mesomorphic behaviours of chiral liquid crystal compounds containing (-)-menthyl. Liq Cryst. 2018;45:1760–1770.
   Web of Science ®Google Scholar
• Zhu ZX, Luo CC, Wang JW, et al. Synthesis and properties of (-)-menthol-derived chiral liquid crystals by introducing adipoyloxy spacer between mesogenic core and chiral menthyl. Liq Cryst. 2018;45:1525–1534.
   Web of Science ®Google Scholar
• Ma X, Wang QC, Qu DH, et al. A light-driven pseudo[4]rotaxane encoded by induced circular dichroism in a hydrogel. Adv Funct Mater. 2007;17:829–837.
   Web of Science ®Google Scholar
• Collings PJ, Hird M. Introduction to liquid crystal chemistry and physics. London: Taylor & Francis; 1997.
   Google Scholar
• Arakawa Y, Inui S, Tsuji H. Novel diphenylacety-lene-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
• Dierking I. Textures of liquid crystals. Weinheim: Wiley-VCH; 2003.
   Google Scholar
• Li Q. Anisotropic nanomaterials: preparation, properties, and applications. Cham: Springer; 2015.
   Google Scholar
• Yu HF. Recent advances in photoresponsive liquid crystalline polymers containing azobenzene chromophores. J Mater Chem C. 2014;2:3047–3054.
   Web of Science ®Google Scholar