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Original Articles

Influence of terminal groups on liquid-crystalline polymorphism of selected azobenzene derivatives

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Pages 113-125 | Received 09 Aug 2013, Accepted 27 Aug 2013, Published online: 25 Sep 2013

References

  • Bahadur B. Liquid crystals: applications and uses. Singapore: World Scientific; 1992.
  • Bogojawlenski A, Winogradov N. Über das Verhalten von Schmelz- und Klärungs kurven flüssiger Kristalle und ihrer Mischungen. Z Phys Chemie. 1908;64:229–242.
  • Kosa T, Sukhomlinova L, Su L, Taheri B, White TJ, Bunning TJ. Light-induced liquid crystallinity. Nature. 2012;485:347–349.
  • Vorländer D. Die Richtung der Kohlenstoff-Valenzen in Benzol-Abkömmlingen. Berichte. 1929;62:2831–2836.
  • Vorländer D, Apel A. Die Richtung der Kohlenstoff-Valenzen in Benzolabkömmlingen (II). Berichte. 1932;65:1101–1109.
  • Vorländer D, Hollatz J, Fischer J. Alkali-borfluoride, Alkali-fluorsulfonate und Kalium-perrhenat. Berichte. 1932;65:535–538.
  • Alaasar M, Prehm M, Tschierske C. Influence of halogen substituent on the mesomorphic properties of five-ring banana-shaped molecules with azobenzene wings. Liq Cryst. 2013;40:656–668.
  • Chan T-N, Lu Z, Yam W-S, Yep G-Y, Imrie CT. Non-symmetric liquid crystal dimers containing an isoflavone moiety. Liq Cryst. 2012;39:393–402.
  • Yeap GY, Balamurugan S, Rakesh S. Synthesis and mesomorphic properties of chiral liquid crystal dimers derived from azobenzene and substituted naphthol. Liq Cryst. 2013;40:555–563.
  • Tomczyk J, Sobolewska A, Nagy ZT, Daniel Guillon D, Donnio B, Stumpe J. Photo- and thermal-processing of azobenzene-containing star-shaped liquid crystals. J Mat Chem C. 2013;1:924–932.
  • Chen S, Ling A, Zhang HL. Synthesis and phase behaviors of side-chain liquid-crystalline polymers containing azobenzene mesogen with the different length alkyl tail. J Polymer Sci A. 2013;51:2759–2768.
  • Yang C, Xie H, Zhong G, Zhang H. The effects of para-, meta- and ortho-mono substituted azobenzene moiety in the side chain on phase behavior of mesogen-jacketed liquid crystalline polymers. Polymer. 2013;54:3238–3247.
  • Martinez-Felipe A, Lu Z, Henderson PA, Picken SJ, Norder B, Imrie CT, Ribes-Greus A. Synthesis and characterisation of side chain liquid crystal copolymers containing sulfonic acid groups. Polymer. 2012;53:2604–2612.
  • Cook AG, Inkster RT, Martinez-Felipe A, Ribes-Greus A, Hamley IW, Imrie CT. Synthesis and phase behaviour of a homologous series of polymethacrylate-based side-chain liquid crystal polymers. Eur Polymer J. 2012;48:821–829.
  • Gutierrez-Cuevas KG, Larios-Lopez L, Rodriguez-Gonzalez JL, Donnio B, Navarro-Rodriguez D. On the liquid-crystalline properties of methacrylic polymers containing 4′-(4- alkyloxyphenyl)azobenzene mesogens. Liq Cryst. 2013;40:534–545.
  • Martinez-Felipe A. Liquid crystal polymers and ionomers for membrane applications. Liq Cryst. 2011;38:1607–1626.
  • Jian-She H, Xia Z, Ying-Gang J, Qing-Bao M. Synthesis and phase behaviour of chiral liquid crystalline monomers based on menthyl groups, smectic polymers and cholesteric elastomers. Liq Cryst. 2012;39:121–131.
  • Gonzales-Antuna A, Lavandera I, Rodrigues-Gonzales P, Rodrigues J, Alonso JIG, Gotor V. A straightforward route to obtain 13C1-labeled clenbuterol. Tetrahedron. 2011;67:5577–5581.
  • Stewart D, Imrie CT. Synthesis and characterization of spin-labelled and spin-probed side-chain liquid crystal polymers. Polymer. 1996;37:3419–3425.
  • Dąbrowski R, Kenig K. Mesomorphic properties of the Homologous Series of 4-n-Propyl-4′-n-alkylazobenzenes and 4-n-Propyl-4′-n-alkyloazoxybenzenes. Biul Pol Acad Sci. 1986;34:183–189.
  • Zienkiewicz J, Galewski Z. Smectic polymorphism of 4-butyl-4′-alkyloxyazobenzenes and 4-pentyl-4′-alkyloxyazobenzenes. Liq Cryst. 1997;23:9–16.
  • Slaney AJ, Goodby JW. Novel chiral mesomorphic compounds based on a-amino acid derivatives: synthesis and properties. J Mat Chem. 1985;5:663–674.
  • Galewski Z, Coles HJ. Liquid crystalline properties and phase situations in 4-chlorobenzylidene-4′-alkylanilines. J Mol Liq. 1999;79:77–87.
  • Murase K, Watanabe H. Liquid crystalline properties of substituted azo and azoxybenzenes. I. Bull Chem Soc Jpn. 1973;46:3142–3143.
  • Zienkiewicz J, Galewski Z. Liquid crystalline properties of 4-methyl-, 4-ethyl- and 4-propyl-4′-alkyloxyazobenzenes. Pol J Chem. 2002;76:359–366.
  • Galewski Z, Hofmanska A, Zielinska K. Liquid crystalline properties of azobenzenes: I: 4-methyloxy-4′-alkyloxyazobenzenes, 4-ethyloxy-4′-alkyloxyazobenzenes, propyloxy-4′-alkyloxyazobenzenes and 4-butyloxy-4′-alkyloxyazobenzenes. Pol J Chem. 1999;73:1357–1371.
  • Galewski Z. Liquid crystalline properties of azobenzenes: II: 4-pentyloxy-4′-alkyloxyazobenzenes, 4-hexyloxy-4′-alkyloxyazobenzenes and 4-heptyloxy-4′-alkyloxyazobenzenes. Pol J Chem. 1999;73:1503–1511.
  • Demus D, Sackmann H. Isomorphiebeziehungen zwischen kristallin-flüssigen Phasen. 5. Mitteilung: Die Umwandlungsvorgänge von 67 Verbindungen mit smektischen Phasen [1,2]. Z Phys Chem. 1963;222:127–142.
  • Dave JS, Menon M. Synthesis and mesomorphic characterization of azoketones. Mol Cryst Liq Cryst. 1998;319:51–60.
  • Galewski Z. unpublished results.
  • Shah NH, Vora RA, Jadav ND. Azomesogens-(II): (A) methyl 4-(4′-n-alkoxyphenylazo)benzoates, (B) n-propyl 4-(4′-n-alkoxyphenylazo)benzoates. In: Chandrasekhar S, editor. Liquid crystals . Proceedings; 1979 Dec 3. Bangalore: Heyden; 1980. p. 56–59.
  • Steinsträsser R, Pohl L. Niedrigschmelzende p-Alkyl-p′-alkoxy und p-Alkyl-p′-acyloxy-azobenzole Z. Naturforsch B. 1972;26:577–580.
  • Vorländer D. Über die Natur der Kohlenstoffketonen in Kristallin-flüssigen Substancen. Z Phys Chem. 1927;126:449–472.
  • McCaffrey M, Castellano J. Liquid crystals VII. The mesomorphic behavior of homologous: p-Alkoxy-p′-Acyloxyazoxybenzenes. Mol Cryst Liq Cryst. 1972;18:209–225.
  • Rondeau R, Berwick M, Steppel R, Serve M. Central linkage influence upon mesomorphic and electrooptical behavior of diary1 nematics. A general proton magnetic resonance method employing a lanthanide shift reagent for analysis of isomeric azoxybenzenes. J Am Chem Soc. 1972;94:1096–1102.
  • Albertini G, Fanelli E, Guillon D, Melone S, Poeti G, Rustichelli F, Torquati G. Mesomorphic properties and molecular structure. II. Structure of the smectic A phase in the 4-propionyl-4′ -n-alkanoyloxy-azo-benzene series. J Phys (Paris). 1984;45:341–346.
  • Albertini G, Fanelli E, Melone S, Rustichelli F, Torquati G. Evidence by X-ray diffraction for hexatic B and crystal B structures in a pure compound. Solid State Comm. 1984;49:1143–1146.
  • Bikchantaev I, Szydlowska J, Pociecha D, Krowczynski A, Gorecka E. Restricted molecular rotation in hexatic B and crystalline B mesophases as studied by the electron paramagnetic resonance method. J Chem Phys. 1997;107:9208–9213.
  • Pyzuk W, Krowczynski A, Szydłowska J, Górecka E. Orthogonal hexatic smectic phase-rare or common? Liq Cryst. 1995;19:85–91.
  • Iannacchione G, Gorecka E, Pyzuk W, Kumar S, Finotello D. Ac-calorimetry studies at the hexatic-B–smectic-A and crystal-B–hexatic-B phase transitions in two compounds with hydrogen bonding. Phys Rev E. 1995;51:3346–3349.
  • Gorecka E, Chen L, Pyzuk W, Krowczynski A, Kumar S. X-ray studies of the hexatic phase in liquid crystals with a crystal-B–hexatic-B–smectic-A phase sequence. Phys Rev E. 1994;50:2863–2867.
  • Imrie CT, Taylor L. The preparation and properties of low molar mass liquid crystals possessing lateral alkyl chains. Liq Cryst. 1989;6:1–10.
  • Donaldson T, Staesche H, Lu ZB, Henderson PA, Achard MF, Imrie CT. Symmetric and non-symmetric chiral liquid crystal dimmers. Liq Cryst. 2010;37:1097–1110.
  • Henderson PA, Niemeyer O, Imrie CT. Methylene-linked liquid crystal dimmers. Liq Cryst. 2001;28:463–472.
  • Henderson PA, Imrie CT. Methylene-linked liquid crystal dimers and the twist-bend nematic phase. Liq Cryst. 2011;38:1407–1414.
  • Nessim RI, Naoum MM, Mohamed SZ, Nessim MI. Effect of molecular structure on the phase behaviour of some liquid crystalline compounds and their mixtures XIII. 4-(4-Substituted phenylazo)phenyl 4-alkoxybenzoates. Liq Cryst. 2004;31:649–654.

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