Synthesis and liquid crystalline investigation of chiral 6-alkoxy-2-naphathoic acid derivatives

References

• Renitzer F. Beiträgezurkenntniss des cholesterins. Monatsh Chem. 1888;9:421–441. doi:10.1007/BF01516710.
   Google Scholar
• Linesmn ME, Glass AM. Principles and applications of ferroelectric and related materials. Oxford: Oxford University Press; 2001.
   Google Scholar
• Pardon L, Ricote J. Multifunctional polycrystalline ferroelectric materials. Dordrech: Springer; 2011.
   Google Scholar
• Kitzerow HS, Bahr C, editors. For an excellent collection of article on this topic, see chirality in liquid crystals. New York, NY: Springer-Verlag; 2001.
   Google Scholar
• Kitzerow HS. Blue phases at work. Chem Phys Chem. 2006;7:63–66. doi:10.1002/cphc.200500506.
   Web of Science ®Google Scholar
• Goodby JW, Nishiyama I, Slaney AJ, et al. Chirality in liquid crystals. The remarkable phenylpropiolates. Liq Cryst. 1993;14:37–66. doi:10.1080/02678299308027303.
   Web of Science ®Google Scholar
• Osipov M. Molecular theories of liquid crystals. In: Goodby JW, Collings PJ, Kato T, et al., editors. Chapter 5, Handbook of liquid crystals. Vol. 1. 2nd ed. Weinheim: Wiley VCH; 2014. p. 115–165.
   Google Scholar
• Yang DK. Flexible bistable cholesteric reflective displays. J Display Technol. 2006;2:32–37. doi:10.1109/JDT.2005.861595.
   Web of Science ®Google Scholar
• A Review by Shashidhar R, Naciri J, Ratna BR. Advances in liquid crystals, a special volume of advances in chemical sciences. Vij JK, editor. New York, NY: John Wiley and Sons Inc.; 2000.
   Google Scholar
• Davis EJ, Goodby JW. Symmetry and chirality in liquid crystals. In: Goodby JW, Collings PJ, Kato T, et al., editors. Chapter 7, handbook of liquid crystals vol 1: fundamentals of liquid crystals. Weinheim: Wiley-VCH; 2014. p. 197–230. ISBN 978-3-527-32773-7.
   Google Scholar
• Chandani DL, Ouchi Y, Takezoe H, et al. Novel phases exhibiting tristables witching. Jpn J Appl Phys. 1989;28:L1261–L1265. doi:10.1143/JJAP.28.L1261.
   Web of Science ®Google Scholar
• Fukuda A, Takanishi Y, Isozaki T, et al. Antiferroelectric chiral smectic liquid crystals. J Mater Chem. 1994;4:997–1016. doi:10.1039/JM9940400997.
   Web of Science ®Google Scholar
• Dhave K, Dahlgren A, Rudquist P, et al. Antiferroelectric liquid crystals with 45° tilt - a new class of promising electro-optic materials. Ferroelectrics. 2000;244:115–128. doi:10.1080/00150190008228422.
   Web of Science ®Google Scholar
• Murthy HNS, Sadashiva BK. Ferroelectric and antiferroelectric switching behaviour in new unsymmetrical bent-core compounds derived from 3-hydroxybenzoic acid. J Mater Chem. 2005;15:2056–2064. doi:10.1039/B419404G.
   Web of Science ®Google Scholar
• Lagerwall ST. Ferroelectric and antiferroelectric liquid crystals. Weinheim: Wiley-VCH; 1999.
   Google Scholar
• Jones JC, Towler MJ, Hughes JR. Fast, high-contrast ferroelectric liquid crystal displays and the role of dielectric biaxiality. Displays. 1993;14:86–93. doi:10.1016/0141-9382(93)90075-G.
   Web of Science ®Google Scholar
• Goodby JW, Leslie TM. Ferroelectric liquid crystals - structure and design. Mol Cryst Liq Cryst. 1984;110:175–203. doi:10.1080/00268948408074505.
   Web of Science ®Google Scholar
• Goodby JW. Properties and structures of ferroelectric liquid crystals in ferroelectric liquid crystals. Taylor GW, editor. Vol. 7, Philadelphia: Gordon and Breach; 1991. p. 99–248.
   Google Scholar
• Meyer RB, Liebert L, Strzelecki L, et al. Ferroelectric liquid crystal. J Phys Lett. 1975;36:L69 L71. doi:10.1051/jphyslet:0197500360306900.
   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. Euro Polym J. 2007;43:2017–2027. doi:10.1016/j.eurpolymj.2007.01.053.
   Web of Science ®Google Scholar
• Griffin AC, Fisher RF, Havens SJ. Effect of molecular structure on mesomorphism.7. Enhancement of smectic-isotropic transition temperatures in binary mixtures of a new liquid crystal series: the 4-nitrophenyl 4ʹ-n-alkoxybenzoates. J Am Chem Soc. 1978;100:6329–6333. doi:10.1021/ja00488a006.
   Web of Science ®Google Scholar
• Kang YS, Kim H, Zin WC. Phase behaviour of hydrogen-bonded liquid crystalline complexes of alkoxyl cinnamic acids with 4,4ʹ-bipyridine. Liq Cryst. 2001;28:709–715. doi:10.1080/02678290010025855.
   Web of Science ®Google Scholar
• Chia WL, Lin CW. Synthesis and thermotrophic studies of a novel series of nematogenic liquid crystals 2-(6-alkoxynaphthalen-2-yl)5-cyanopyridines. Liq Cryst. 2013;40:922–931. doi:10.1080/02678292.2013.786793.
   Web of Science ®Google Scholar
• Thaker BT, Patel BS, Dhimmar YT, et al. Mesomorphic studies of novel azomesogens having a benzothiazole core: synthesis and characterisation. Liq Cryst. 2013;40:237–248. doi:10.1080/02678292.2012.737478.
   Web of Science ®Google Scholar
• Kovarova A, Kozmik V, Svoboda J, et al. Naphthalene-based bent shaped liquid crystals with a semifluorinated terminal chain. Liq Cryst. 2012;39:755–767. doi:10.1080/02678292.2012.678396.
   Web of Science ®Google Scholar
• Thaker BT, Chothani NJ, Dhimmar YT, et al. Synthesis, characterisation and liquid crystalline properties of some Schiff base-ester central linkage involving 2, 6-disubstituted naphthalene ring system. Liq Cryst. 2012;39:551–569. doi:10.1080/02678292.2012.664175.
   Web of Science ®Google Scholar
• Praveen PL, Ojha DP. Photosensitivity, substituent and solvent-induced shifts in UV-visible absorption bands of naphthyl-ester liquid crystals: a comparative theoretical approach. Liq Cryst. 2014;41:872–882. doi:10.1080/02678292.2014.882423.
   Web of Science ®Google Scholar
• Vajda A, Kaspar M, Hamplova V, et al. Phase diagrams and physical properties of binary ferroelectric mixtures based on a series of chiral α-cyanocinnamate derivatives. Liq Cryst. 2002;29:1347–1354. doi:10.1080/713935627.
   Web of Science ®Google Scholar
• Yelamaggad CV, Shanker G. Synthesis and characterization of non‐symmetric chiral dimmers. Liq Cryst. 2007;34:1045–1057. doi:10.1080/02678290701616280.
   Web of Science ®Google Scholar
• Bialecka-Florjanczyk E, Przedmojski J. Liquid crystalline esters of (E)-3-phenoxyacrylic acid. J Mater Chem. 2002;12:553–556. doi:10.1039/B105961K.
   Web of Science ®Google Scholar
• Prajapati AK, Patel HN. Mesogenic cinnamates with a substituted ethyl terminal chain. Liq Cryst. 2007;34:903–910. doi:10.1080/02678290701243846.
   Web of Science ®Google Scholar
• Van der Zande BMI, Lub J, Verhoef HJ, et al. Patterned retarders prepared by photoisomerization and photopolymerization of liquid crystalline films. Liq Cryst. 2006;29:723–737. doi:10.1080/02678290600647345.
   Web of Science ®Google Scholar
• Enz E, Tandel SF, Dabrowski R, et al. On the balance between syn- and anticlinicity in smectic phases formed by achiral hockey-stick mesogens with and without chiral dopants. J Mater Chem. 2009;19:2950–2957. doi:10.1039/B820717H.
   Web of Science ®Google Scholar
• Bobrovsky A, Shibaev V, Hamplova V, et al. Photoinduced phase transitions and helix untwisting in the SmC* phase of a novel cinnamoyl-based liquid crystal. Liq Cryst. 2009;36:989–997. doi:10.1080/02678290903171696.
   Web of Science ®Google Scholar
• Chakraborty A, Das B, Das MK, et al. New hockey stick compounds with a lateral methyl group showing nematic, synclinic and anticlinic smectic C phases. Liq Cryst. 2011;38:1085–1097. doi:10.1080/02678292.2011.596227.
   Web of Science ®Google Scholar
• Li X, Cui J, Zhang W, et al. Controllable photo-switching of cinnamate-based photonic films with remarkable stability. J Mater Chem. 2011;21:17953–17959. doi:10.1039/C1JM11708D.
   Web of Science ®Google Scholar
• Tokita M, Uitoh M, Marumo K, et al. Macrocyclised pheynylcinnamate dimer utilisable as photoresponsive chiral dopant for nematic liquid crystals. Liq Cryst. 2013;40:900–905. doi:10.1080/02678292.2013.790094.
   Web of Science ®Google Scholar
• Tandel RC, Patel NK. Synthesis and mesomorphic properties of chiral nematic liquid crystals based on cholesterol. Liq Cryst. 2014;41:514–521. doi:10.1080/02678292.2013.861031.
   Web of Science ®Google Scholar
• Jones FB, Ratto JJ In proceedings of the Fifth International Liquid Crystal Conference, Stockholm, Sweden; 1974.
   Google Scholar
• Cui L, Xie P, Zhang RB. Photo-driven liquid crystal cell with high sensitivity. Liq Cryst. 1999;26:1541–1546. doi:10.1080/026782999203878.
   Web of Science ®Google Scholar
• Kishikawa K, Itoh H, Akiyama S, et al. Stabilization of the blue phases of simple rodlike monoester compounds by addition of their achiral homologues. J Mater Chem. 2012;22:8484–8491. doi:10.1039/C2JM16359D.
   Web of Science ®Google Scholar
• Hird M. Ferroelectricity in liquid crystals—materials, properties and applications. Liq Cryst. 2011;38:1467–1493. doi:10.1080/02678292.2011.625126.
   Web of Science ®Google Scholar
• Melon-Ksyta D, Orzeszko A, Borys W, et al. Synthesis and liquid crystalline properties of monothio- and dithioimides with chiral N-substituents. J Mater Chem. 2002;12:1311–1315. doi:10.1039/B111391G.
   Web of Science ®Google Scholar
• Kaminska A, Mieczkowski J, Pociecha D, et al. Synthesis and liquid crystalline properties of monothio- and dithioimides with chiral N-substituents. J Mater Chem. 2003;13:475–478. doi:10.1039/B111391G.
   Web of Science ®Google Scholar
• Sun GX, Chen B, Tang H, et al. Synthesis and physical properties of novel liquid crystals containing 2,3-difluorophenyl and 1,3-dioxane units. J Mater Chem. 2003;13:742–748. doi:10.1039/B210765A.
   Web of Science ®Google Scholar
• Dzik E, Mieczkowski J, Gorecka E, et al. Ferroelectric, ferrielectric and antiferroelectric mesophases in compounds with a polybenzyloxycarbonyl mesogenic core. J Mater Chem. 2005;15:1255–1262. doi:10.1039/B417144F.
   Web of Science ®Google Scholar
• Yang H, Wang L, Shao R, et al. Novel liquid-crystalline mesogens and main-chain chiral smectic thiol-ene polymers based on trifluoromethylphenyl moieties. J Mater Chem. 2009;19:7208–7215. doi:10.1039/B907907F.
   Web of Science ®Google Scholar
• Fergusson KM, Hird M. The dramatic influence of the location of bend and of lateral fluoro substitution on the mesomorphic properties of angular chiral esters based on a 1,3-disubstituted benzene ring. J Mater Chem. 2010;20:3069–3078. doi:10.1039/b923267b.
   Web of Science ®Google Scholar
• Novotna V, Hamplova V, Podoliak N, et al. Chiral liquid crystalline compounds with a re-entrant SmA* phase. J Mater Chem. 2011;21:14807–14814. doi:10.1039/C1JM12131F.
   Web of Science ®Google Scholar
• Ho CY, Wang LS, Lin FH, et al. Synthesis and mesomorphic properties of chiral smectic A phase liquid crystals of wide temperature range. Liq Cryst. 2011;38:381–390. doi:10.1080/02678292.2010.550068.
   Web of Science ®Google Scholar
• Hu JS, Zhang WC, Su D, et al. New side chain ferroelectric liquid crystalline polymers based on (2S, 3S)-2-chloro-3-methylpentanoic acid: synthesis and phase behavior. Liq Cryst. 2014;41:1526–1536. doi:10.1080/02678292.2014.929751.
   Web of Science ®Google Scholar
• Coates D. Development and applications of cholesteric liquid crystals. Liq Cryst. 2000;27:1103–1112. doi:10.1080/02678292.2015.1020454.
   Web of Science ®Google Scholar
• Gray GW, Jones B. Mesomorphism and chemical constitution. Part II. The trans-p-n-alkoxycinnamic acids. J Chem Soc. 1954;678–683. doi:10.1039/JR9540001467.
   Web of Science ®Google Scholar
• Lin HC, Shiaw JM, Wu CY, et al. Fused-ring and linking group effects of proton donors and acceptors on simple H-bonded liquid crystals. Liq Cryst. 2000;27:1103–1112. doi:10.1080/02678290050080869.
   Web of Science ®Google Scholar
• Neises B, Steglich W. Simple method for the esterification of carboxylic acids. Angew Chem Int Edit Engl. 1978;17:522–524. doi:10.1002/anie.197805221.
   Web of Science ®Google Scholar
• Subrahmanyam SV, Chalapathi PV, Mahabaleswara S, et al. Ferroelectric phases in non-symmetric achiral bent liquid crystals towards ambient temperatures: a novel series with oxadiazol as central. Liq Cryst. 2014;41:1130–1151. doi:10.1080/02678292.2014.908478.
   Web of Science ®Google Scholar
• Chan TN, Lu Z, Yam WY, et al. Non-symmetric liquid crystal dimers containing an isoflavone moiety. Liq Cryst. 2012;39:393–402. doi:10.1080/02678292.2012.658712.
   Web of Science ®Google Scholar
• Lohar JM, Mashru U. Schiffs base homologous series of new mesogens: p-(p′-n-alkoxycinnamoyloxy) benzylidene-p″-N, N-dimethylaminoanilines and p-(p′-n-alkoxycinnamoyloxy) benzylidene-p″-N, N-diethylaminoanilines. Mol Cryst Liq Cryst. 1981;70:29–38. doi:10.1080/00268948108073577.
   Google Scholar
• Gray GW. Molecular structure and properties of liquid crystals. London: Academic Press; 1962.
   Google Scholar