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Articles

Smectic behaviour of methyl 4-alkoxybenzoates with a partially fluorinated alkyl chain

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Pages 11-21 | Received 09 Dec 2016, Accepted 30 Jan 2017, Published online: 15 Feb 2017

References

  • Tschierske C. Microsegregation in liquid crystalline systems: basic concepts. In: Goodby JW, Collings PJ, Kato T, et al., editors. Handbook of liquid crystals. Weinheim: wiley-VCH. Vol. 5. 2014. pp. 1–43. Weinheim: Wiley-VCH Verlag&Co.
  • Tschierske C. Fluorinated liquid crystals: design of soft nanostructures and increased complexity of self-assembly by perfluorinated segments. Top Curr Chem. 2012;318:1–108.
  • Tschierske C. Non-conventional liquid crystals - the importance of micro-segregation for self-organisation. J Mater Chem. 1998;8:1485–1508.
  • Hird M. Fluorinated liquid crystals - properties and applications. Chem Soc Rev. 2007;36:2070–2095.
  • Ciastek S, Kaszyński P, Pociecha D, et al. Induction of smectic polymorphism in bent-core derivatives of the 6-oxoverdazyl by partial fluorination of alkyl chains. RSC Adv. 2016;6:102343–102347.
  • Viney C, Russell TP, Depero LE, et al. Transitions to liquid crystalline phases in a semifluorinated alkane. Mol Cryst Liq Cryst. 1989;168:63–82.
  • Viney C, Twieg RJ, Russell TP, et al. The structural basis of transitions between highly ordered smectic phases in semifluorinated alkanes. Liq Cryst. 1989;5:1783–1788.
  • Krafft MP, Riess JG. Chemistry, physical chemistry, and uses of molecular fluorocarbon−hydrocarbon diblocks, triblocks, and related compoundsↃunique “apolar” components for self-assembled colloid and interface engineering. Chem Rev. 2009;109:1714–1792. doi:10.1021/cr800260k
  • Takenaka S. Thermal properties of novel liquid crystals having a single benzene unit. J Chem Soc Chem Commun. 1992;1992:1748–1749.
  • Bao X, Dix LR. Smectic phases observed in 1, 1,2,2,-tetrahydroperfluoroalkyl-4-nitrobenzoates. Mol Cryst Liq Cryst. 1996;281:291–294.
  • Johansson G, Percec V, Ungar G, et al. Fluorophobic effect generates a systematic approach to the synthesis of the simplest class of rodlike liquid crystals containing a single benzene unit. Chem Mater. 1997;9:164–175.
  • Duan M, Okamoto H, Petrov VF, et al. A new mesomorphism of the alkyl 4-(2-perfluoroalkyl)ethoxybenzoate derivatives. Bull Chem Soc Jpn. 1998;71:2735–2739.
  • Okamoto H, Murai H, Takenaka S. Liquid-crystalline properties of alkyl 4-[2-(perfluorooctyl)ethoxy]benzoates. Bull Chem Soc Jpn. 1997;70:3163–3166.
  • Fornasieri G, Guittard F, Géribaldi S. Microphasic separation-induced enantiotropic liquid crystal behaviour single phenyl unit series based on the fluorophobic effect. Liq Cryst. 2003;30:663–669.
  • Twieg R, Betterton K, DiPietro R, et al. Remarkable influence of fluorination in smectic and ferroelectric liquid crystals. Mol Cryst Liq Cryst. 1992;217:201–206.
  • Schaz A, Valaityte E, Lattermann G. Investigations on liquid crystalline partially fluorinated ‘one-chain’ and ‘two-chain’ benzoic acids. Liq Cryst. 2004;31:1311–1321.
  • Khairuddean M, Twieg RJ. Liquid crystals derived from semifluorinated alkoxybenzoyl hydrazines. Mol Cryst Liq Cryst. 2009;503:3–31.
  • Schaz A, Valaityte E, Lattermann G. Investigations on liquid crystalline partially fluorinated alkyl and succinimidyl benzoates. Liq Cryst. 2005;32:513–525.
  • Nguyen HT, Rouillon JC, Babeau A, et al. Synthesis, properties and crystal structure of chiral semiperfluorinated liquid crystals with ferro and anticlinic smectic phases. Liq Cryst. 1999;26:1007–1019.
  • Woody KB, Nambiar R, Brizius GL, et al. Synthesis and properties of amphiphilic poly(1,4-phenylene ethynylene)s bearing alkyl and semifluoroalkyl substituents. Macromolecules. 2009;42:8102–8111.
  • Luscombe CK, Proemmel S, Huck WTS, et al. Synthesis of supercritical carbon dioxide soluble perfluorinated dendrons for surface modification. J Org Chem. 2007;72:5505–5513.
  • Chiba K, Kurogi K, Monde K, et al. Super water- and highly oil-repellent films made of fluorinated poly(alkylpyrroles). Colloids and surfaces A: physicochem. Eng Aspects. 2010;354:234–239.
  • Anh DT, Blancou H, Commeyras A. Synthèse d’acides ω perfluoroalkylalcanoı̈ques et d’ω perfluoroalkylalcanols [Synthesis of ω-perfluoroalkylalkanoic acids from ω-perfluoroalkonols]. J Fluorine Chem. 1999;96:167–174.
  • Foulard G, Brigaud T, Portella C. Sequential radical perfluoroalkylation - nucleophilic cyclization. Synthesis of 2-perfluoroalkylidenemethyl and 2-perfluoroalkylmethyl-1,4-dioxanes from 1-O-allyl-1,2-diols. Tetrahedron. 1996;52:6187–6200.
  • Guo J, Resnick P, Efimenko K, et al. Alternative fluoropolymers to avoid the challenges associated with perfluorooctanoic acid. Ind Eng Chem Res. 2008;47:502–508.
  • Parlato MC, Jee J-P, Teshite M, et al. Synthesis, characterization, and applications of hemifluorinated dibranched amphiphiles. J Org Chem. 2011;76:6584–6591.
  • Nguyen JD, D’Amato EM, Narayanam JMR, et al. Engaging unactivated alkyl, alkenyl and aryl iodides in visible-light-mediated free radical reactions. Nature Chemistry. 2012;4:854–859.
  • Kohlmeier A, Janietz D. Hydrogen-bonded polyphilic block mesogens with semiperfluorinated segments. Chem Mater. 2006;18:59–68.
  • Ragnoli M, Pucci E, Bertolucci M, et al. Effects of chemical variations on the mesophase behavior of new fluorinated poly(vinylcyclopropane)s. J Fluorine Chem. 2004;125:283–292.
  • Alvey LJ, Meier R, Soós T, et al. Syntheses and carbonyliridium complexes of unsymmetrically substituted fluorous trialkylphosphanes: precision tuning of electronic properties, including insulation of the perfluoroalkyl groups. Eur J Inorg Chem. 2000;2000:1975–1983.
  • Zenasni O, Jamison AC, Marquez MD, et al. Self-assembled monolayers on gold generated from terminally perfluorinated alkanethiols bearing propyl vs. ethyl hydrocarbon spacers. J Fluorine Chem. 2014;168:128–136.
  • Jo JC, Kim JM, Ahn SO, et al., inventors; Chugai Seiyaku Kabushiki Kaisha (Tokyo, JP), assignee. 3-ethyl-, 3-propyl- or 3-butyl-chroman and thiochroman derivatives. United States Patent 6,552,068. 2003 Apr 22.
  • Jo JC, Na YJ, Heo HI, et al., inventors; Chugai Seiyaku Kabushiki Kaisha (Tokyo, JP), assignee. 3-methyl-chroman and -thiochroman derivatives. United States Patent 6,552,069. 2003 Apr 22.
  • Lukáč M, Garajová M, Mrva M, et al. Novel fluorinated dialkylphosphonatocholines: synthesis, physicochemical properties and antiprotozoal activities against acanthamoeba spp. J Fluorine Chem. 2014;164:10–17.
  • De Campo F, Lastécouères D, Vincent J-M, et al. Copper(I) complexes mediated cyclization reaction of unsaturated ester under fluoro biphasic procedure. J Org Chem. 1999;64:4969–4971.
  • Ang WJ, Lam Y. Allylic and benzylic sp3 C-H oxidation in water. Org Biomol Chem. 2015;13:1048–1052.
  • Ocak H, Bilgin-Eran B, Tschierske C, et al. Effect of fluorocarbon chains on the mesomorphic properties of chiral imines and their complexes with copper(II). J Mater Chem. 2009;19:6995–7001.
  • Ober CK, Malliaras G, Lee J-K, et al., inventors; Cornell University, assignee. Orthogonal processing of organic materials used in electronic and electrical devices. United States Patent 9,500,952. 2016 Nov 22.
  • Pociecha D, Ohta K, Januszko A, et al. Symmetric bent-core mesogens with m-carborane and adamantane as the central units. J Mater Chem. 2008;18:2978–2982.
  • Kovářová A, Kozmík V, Svoboda J, et al. Naphthalene-based bent-shaped liquid crystals with a semifluorinated terminal chain. Liq Cryst. 2012;39:755–767.
  • Small AC, Pugh C. Induction of smectic layering in nematic liquid crystals using immiscible components. 5. Laterally attached side-chain liquid crystalline poly(norbornene)s and their low molar mass model compounds with short fluorocarbon segments. Macromolecules. 2002;35:2105–2115.
  • Arehart SV, Pugh C. Induction of smectic layering in nematic liquid crystals using immiscible components. 1. Laterally attached side-chain liquid crystalline poly(norbornene)s and their low molar mass analogs with hydrocarbon/fluorocarbon substituents. J Am Chem Soc. 1997;119:3027–3037.
  • Percec V, Schlueter D, Kwon YK, et al. Dramatic Stabilization of a Hexagonal Columnar Mesophase Generated from Supramolecular and Macromolecular Columns by the Semifluorination of the Alkyl Groups of Their Tapered Building Blocks. Macromolecules. 1995;28:8807–8818.
  • Percec V, Johansson G, Ungar G, et al. Fluorophobic Effect Induces the Self-Assembly of Semifluorinated Tapered Monodendrons Containing Crown Ethers into Supramolecular Columnar Dendrimers Which Exhibit a Homeotropic Hexagonal Columnar Liquid Crystalline Phase. J Am Chem Soc. 1996;118:9855–9866.
  • Andruzzi L, Chiellini E, Galli G, et al. Engineering low surface energy polymers through molecular design: synthetic routes to fluorinated polystyrene-based block copolymers. J Mater Chem. 2002;12:1684–1692.
  • Yano M, Taketsugu T, Hori K, et al. The effect of fluorination: a crystallographic and computational study of mesogenic alkyl 4-[2-(perfluorooctyl)ethoxy]benzoates. Chem Eur J. 2004;10:3991–3999.
  • Hori K, Maeda M, Yano M, et al. The effect of fluorination (2): dependence of alkyl chain length on the crystal structures of mesogenic alkyl 4-[2-(perfluorohexyl)ethoxy]benzoates. Liq Cryst. 2011;38:287–293.
  • Martin A, Mügge C, Gin DL, et al. Combined stabilizing effects of trifluoromethyl groups and semifluorinated side chains on the thermotropic liquid-crystal behavior of β-enamino ketone ligands and their bischelate Pd II complexes. Eur J Inorg Chem. 2014;5609–5617.

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