Synthesis and properties of (−)-menthol-derived chiral liquid crystals by introducing adipoyloxy spacer between mesogenic core and chiral menthyl

References

• Solladie G, Zimmermann RG. Liquid crystals: a tool for studies on chirality. Angew Chem Int Ed. 1984;23:348–362.
   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
• 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
• 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
• 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
• Lemieux RP. Molecular recognition in chiral smectic liquid crystals: the effect of core core interactions and chirality transfer on polar order. Chem Soc Rev. 2007;36:2033–2045.
   PubMed Web of Science ®Google Scholar
• Abberley JP, Killah R, Walker R, et al. Heliconical smectic phases formed by achiral molecules. Nat Commun. 2018;9:1–7.
   PubMed Web of Science ®Google Scholar
• Lee M, Hur ST, Higuchi H, et al. Liquid crystalline blue phase I observed for a bent-core molecule and its electro-optical performance. J Mater Chem. 2010;20:5813–5816.
   Web of Science ®Google Scholar
• Li MH, Laux V, Nguyen HT, et al. Blue phases and twist grain boundary phases (TGBA and TGBC) in a series of fluoro-substituted chiral tolane derivatives. Liq Cryst. 1997;23:389–408.
   Web of Science ®Google Scholar
• Brettar J, Burgi T, Donnio B, et al. Ferrocene-containing optically active liquid-crystalline side-chain polysiloxanes with planar chirality. Adv Funct Mater. 2006;16:260–267.
   Web of Science ®Google Scholar
• Hu JS, Li Q, Liu YN, et al. New chiral liquid crystal monomers and cholesteric polyacrylates: synthesis and characterisation. Liq Cryst. 2013;40:1095–1104.
   Web of Science ®Google Scholar
• Suda K, Akagi K. Electro-optical behavior of ferroelectric liquid crystalline polyphenylene derivatives. J Polymer Sci a-Polymer Chem. 2008;46:3591–3610.
   Web of Science ®Google Scholar
• Shibaev PV, Kopp VI, Genack AZ. Photonic materials based on mixtures of cholesteric liquid crystals with polymers. J Phys Chem B. 2003;107:6961–6964.
   Web of Science ®Google Scholar
• Shibaev V, Bobrovsky A, Boiko N, et al. Field-responsive chiral-photochromic side-chain liquid-crystalline polymers. Polym Int. 2000;49:931–936.
   Web of Science ®Google Scholar
• Singh U, Davis F, Mohan S, et al. Electro-active nanofibres electrospun from blends of poly-vinyl cinnamate and a cholesteric liquid crystalline silicone polymer. J Mater Sci. 2013;48:7613–7619.
   Web of Science ®Google Scholar
• Wang W, Liu RG, Liu WL, et al. Hierarchical mesoporous silica prepared from ethyl-cyanoethyl cellulose cholesteric liquid crystalline phase. J Mater Sci. 2010;45:5567–5573.
   Web of Science ®Google Scholar
• Wu SL, Huang FK, Uang BJ, et al. Antiferroelectric liquid crystals derived from a new optically active (R)-3-ethylmercapto-2-methylpropionic acid. Liq Cryst. 1995;18(5):715–721.
   Web of Science ®Google Scholar
• Hiremath US. Synthesis and characterization of novel chiral dimers exhibiting highly frustrated liquid crystal phases. Tetrahedron. 2014;70:4745–4753.
   Web of Science ®Google Scholar
• Guo ZH, Li Q, Liu XF, et al. Synthesis and phase behaviour of new biodegradable liquid crystalline polycarbonate derived from side chain cholesteryl derivative. Liq Cryst. 2016;43:91–101.
   Web of Science ®Google Scholar
• Gorecka E, Vaupotic N, Zep A, et al. A twist-bend nematic (N-TB) phase of chiral materials. Angewandte Chemie-International Edition. 2015;54:10155–10159.
   PubMed Web of Science ®Google Scholar
• Cseh L, Mang XB, Zeng XB, et al. Helically twisted chiral arrays of gold nanoparticles coated with a cholesterol mesogen. J Am Chem Soc. 2015;137:12736–12739.
   PubMed 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 Interfaces. 2016;8:4918–4926.
   PubMed Web of Science ®Google Scholar
• Jia YG, Han LJ, Sun T, et al. Synthesis and mesomorphic behavior of chiral liquid crystalline elastomers derived from (S)-(-)-2-Methyl-1-butanol. Advanced Mater Res. 2013;750-752:863–866.
   Google Scholar
• Lee SK, Tokita M, Shimbo Y, et al. Ferroelectric and antiferroelectric behavior in chiral bent-shaped molecules with an asymmetric central naphthalene core. Bull Korean Chem Soc. 2007;28:2241–2247.
   Web of Science ®Google Scholar
• Merlo AA, Ritter OMS, Pereira FV, et al. Chiral liquid-crystalline polyacrylates from (S)-(-)-2-methyl-1-butanol. Synthesis, mesomorphic properties and light scattering. J Braz Chem Soc. 2001;12:184–191.
   Web of Science ®Google Scholar
• Zhang BY, Hu JS, Yang LQ, et al. Synthesis, structure and mesomorphic properties of side-chain chiral liquid crystalline polysiloxanes based on (S)-(+)-2-methyl-1-butanol derivatives. Eur Polym J. 2007;43:2017–2027.
   Web of Science ®Google Scholar
• Wang AH, Kawabata K, Kawashima H, et al. Synthesis of a pyrimidine-based new chiral inducer for construction of cholesteric liquid crystal electrolyte solution and its electrochemical polymerization, and stimulated emission like interference. Polymer. 2013;54:3821–3827.
   Web of Science ®Google Scholar
• Chiang WY, Hong LD. The synthesis and properties of side chain liquid crystal polymers with a chiral center. J Polym Sci Part A: Polym Chem. 2000;38:1609–1617.
   Web of Science ®Google Scholar
• Nishiyama I, Chin E, Goodby JW. Ferrielectric and antiferroelectric properties of a fluoro-substituted biphenyl ester. J Mater Chem. 1993;3:161–168.
   Web of Science ®Google Scholar
• Garic M, Bubnov A, Novotna V, et al. New ferroelectric liquid crystalline materials containing one and two lactate groups attached to the molecular core. Liq Cryst. 2005;32:565–572.
   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, Hamplova V, Sasnouski G, et al. Lactic acid derivatives with terphenyl molecular core. Liq Cryst. 2016;43:1251–1258.
   Web of Science ®Google Scholar
• Nguyen HT, Ismaili M, Isaert N, et al. Novel chiral liquid crystal with two chiral butyl lactate chains exhibiting several frustrated mesophases including smectic Q and TGB phases separated by an optically isotropic phase. J Mater Chem. 2004;14:1560–1566.
   Web of Science ®Google Scholar
• Kohout M, Bubnov A, Sturala J, et al. Effect of alkyl chain length in the terminal ester group on mesomorphic properties of new chiral lactic acid derivatives. Liq Cryst. 2016;43:1472–1485.
   Web of Science ®Google Scholar
• Xu ZX, Yao M, Feng WJ, et al. 1,2-Propanediol-linked chiral symmetric and non-symmetric liquid crystal dimers containing trifluoromethyl. Liq Cryst. 2016;43:1846–1861.
   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
• 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
• Li YY, Cong YH, Chu HS, et al. Blue phases induced by rod-shaped hydrogen-bonded supermolecules possessing no chirality or mesomorphic behaviour. J Mater Chem C. 2014;2:1783–1790.
   Web of Science ®Google Scholar
• Prajapati AK, Patel NS, Lad VG. Induction of chirality by doping mesogens with non-mesogenic chiral dopant. Molecular Crystals Liquid Crystals. 2000;348:41–51.
   Web of Science ®Google Scholar
• Kozachenko A, Nazarenko V, Sorokin V, et al. Synthesis and properties of chiral dopants synthesized on the base of 2-methylbutanol and e-menthol. Mol Cryst Liquid Cryst Sci Technol Section a-Mol Cryst Liquid Cryst. 1998;324:251–256.
   Web of Science ®Google Scholar
• Chilaya CDGS, Elashvili ZM, Loginov BA, et al. Ferroelectric liquid crystal mixtures induced by mentol derivatives. Ferroelectrics. 1988;85:479–484.
   Web of Science ®Google Scholar
• Yoshioka T, Ogata T, Nonaka T, et al. Reversible-photon-mode full-color display by means of photochemical modulation of a helically cholesteric structure. Advanced Mater. 2005;17:1226–1229.
   Web of Science ®Google Scholar
• Bobrovsky AY, Boiko NI, Shibaev VP, et al. New chiral nematic materials with photovariable helical supramolecular structure for reversible optical data recording. Advanced Mater. 2000;12:1180–1183.
   Web of Science ®Google Scholar
• Liu JH, Yang PC. Synthesis and characterization of novel monomers and polymers containing chiral (-)-menthyl groups. Polymer. 2006;47:4925–4935.
   Web of Science ®Google Scholar
• Jim CKW, Lam JWY, Leung CWT, et al. Helical and luminescent disubstituted polyacetylenes: synthesis, helicity, and light emission of poly(diphenylacetylene)s bearing chiral menthyl pendant groups. Macromolecules. 2011;44:2427–2437.
   Web of Science ®Google Scholar
• Hu JS, Li D, Zhang WC, et al. Synthesis, structure, and properties of chiral liquid crystal monomers and polymers based on menthol. J Polymer Sci a-Polymer Chem. 2012;50:5049–5059.
   Web of Science ®Google Scholar
• Hu JS, Liu XF, Meng QB, et al. New chiral liquid crystalline monomers, polymers, and elastomers derived from menthol derivatives: synthesis and mesomorphism. J Mater Sci. 2014;49:1229–1239.
   Web of Science ®Google Scholar
• Hu JS, Wei KQ, Zhang BY, et al. Synthesis, structure and properties of new chiral liquid crystalline monomers and homopolysiloxanes containing menthyl groups. Liq Cryst. 2008;35:925–935.
   Web of Science ®Google Scholar
• Hu JS, Zhang X, Jia YG, et al. Synthesis and phase behaviour of chiral liquid crystalline monomers based on menthyl groups, smectic polymers and cholesteric elastomers. Liq Cryst. 2012;39:121–131.
   Web of Science ®Google Scholar
• Jia YG, Hu JS, Li D, et al. Synthesis and phase behavior of chiral liquid crystalline polymeric networks derived from menthol. High Perform Polym. 2012;24:673–682.
   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, 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
• 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
• 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
• Naoum MM, Fahmi AA, Ahmed NHS, et al. The effect of lateral methyl substitution on the mesophase behaviour of aryl 4-alkoxyphenylazo benzoates. Liq Cryst. 2015;2:1627–1637.
   Google Scholar
• Naoum MM, Fahmi AA, Ahmed NHS, et al. The effect of inversion of the ester group on the mesophase behaviour of some azo/ester compounds. Liq Cryst. 2015;42:1298–1308.
   Web of Science ®Google Scholar
• Chan TN, Lu Z, Yam WS, et al. Non-symmetric liquid crystal dimers containing an isoflavone moiety. Liq Cryst. 2012;39:393–402.
   Web of Science ®Google Scholar
• Henderson PA, Seddon JM, Imrie CT. Methylene- and ether-linked liquid crystal dimers II. Effects of Mesogenic Linking Unit and Terminal Chain Length. Liq Cryst. 2005;32:1499–1513.
   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
• Dierking I. Textures of liquid crystals. Weinheim: Wiley-VCH; 2003.
   Google Scholar