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Article

Experimental and theoretical approaches of molecular geometry and mesophase behaviour relationship of laterally substituted azopyridines

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Pages 1440-1451 | Received 30 Dec 2018, Accepted 07 Feb 2019, Published online: 01 Mar 2019

References

  • Chen H-W, Lee J-H, Lin B-Y, et al. Liquid crystal display and organic light-emitting diode display: present status and future perspectives. Light Sci Appl. 2018;7:17168.
  • Muševič I. Liquid-crystal micro-photonics. Liq Cryst Rev. 2016;4:1–34.
  • Zhou P, Li Y, Li X, et al. Holographic display and storage based on photo-responsive liquid crystals. Liq Cryst Rev. 2016;4:83–100.
  • Foffano G, Lintuvuori J, Tiribocchi A, et al. The dynamics of colloidal intrusions in liquid crystals: a simulation perspective. Liq Cryst Rev. 2014;2:1–27.
  • Lin Y-H, Wang Y-J RV. Liquid crystal lenses with tunable focal length. Liq Cryst Rev. 2017;5:111–143.
  • Klimusheva G, Mirnaya T, Garbovskiy Y. Versatile nonlinear-optical materials based on mesomorphic metal alkanoates: design, properties, and applications. Liq Cryst Rev. 2015;3:28–57.
  • Bogojawlensky A, Winogradow N. Über das Verhalten von Schmelz-und Klärungskurven flüssiger Kristalle und ihrer Mischungen. Z Phys Chem. 1908;64:229–242.
  • Liu D, Broer DJ. Liquid crystal polymer networks: switchable surface topographies. Liq Cryst Rev. 2013;1:20–28.
  • Saravanan C, Senthil S, Kannan P. Click chemistry‐assisted triazole‐substituted azobenzene and fulgimide units in the pendant‐based copoly (decyloxymethacrylate) s for dual‐mode optical switches. J Polym Sci A Polym Chem. 2008;46:7843–7860.
  • Rochon P, Batalla E, Natansohn A. Optically induced surface gratings on azoaromatic polymer films. Appl Phys Lett. 1995;66:136–138.
  • Eremin A, Nádasi H, Hirankittiwong P, et al. Azodendrimers as a photoactive interface for liquid crystals. Liq Cryst. 2018;45:2121–2131.
  • Ube T, Yoda T, Ikeda T. Fabrication of photomobile polymer materials with phase-separated structure of crosslinked azobenzene liquid-crystalline polymer and poly (dimethylsiloxane). Liq Cryst. 2018;45:2269–2273.
  • Natansohn A, Rochon P. Photoinduced motions in azo-containing polymers. Chem Rev. 2002;102:4139–4176.
  • Yuquan S, Ling Q, Zao L, et al. The second-order nonlinear optical properties of a series of polyesters containing push-pull azobenzene chromophore in their side chain. J Mater Sci. 1999;34:1513–1517.
  • Qiu L, Shen Y, Hao J, et al. Study on novel second-order NLO azo-based chromophores containing strong electron-withdrawing groups and different conjugated bridges. J Mater Sci. 2004;39:2335–2340.
  • 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.
  • 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 dimer. J Am Chem Soc. 2016;138:5283–52899.
  • Pelzl G, Diele S, Weissflog W. Banana‐shaped compounds—a new field of liquid crystals. Adv Mater. 1999;11:707–724.
  • Yu H, Szilvási T, Rai P, et al. Computational chemistry‐guided design of selective chemoresponsive liquid crystals using pyridine and pyrimidine functional groups. Adv Funct Mater. 2018;28:1703581.
  • Ong L-K, Ha S-T, Yeap G-Y, et al. Heterocyclic pyridine-based liquid crystals: synthesis and mesomorphic properties. Liq Cryst. 2018;45:1574–1584.
  • Ren Y, Zhang Y, Yao X. QSPRs for estimating nematic transition temperatures of pyridine-containing liquid crystalline compounds. Liq Cryst. 2018;45:238–249.
  • Chia W-L, Huang Y-S. Effect of pyridine on the mesophase of teraryl liquid crystals: a new series of nematic liquid crystals named 2-(4-alkoxybiphen-4′-yl)-5-methylpyridines. Int J Mol Sci. 2016;17:344.
  • Chen R, Qin Y, An Z, et al. The effect of phenyl ring on the physical properties of liquid crystals containing 4-pyridyl terminal group. Liq Cryst. 2018;45:1825–1833.
  • Zaki AA, Ahmed H, Hagar M. Impact of fluorine orientation on the optical properties of difluorophenylazophenyl benzoates liquid crystal. Mater Chem Phys. 2018;216:316–324.
  • Ahmed HA, El-Sayed TH, Alnoman R. Schiff base/ester liquid crystals with different lateral substituents: mesophase behaviour and DFT calculations. Liq Cryst. in press. doi: 10.1080/02678292.2019.1566581
  • Naoum MM, Metwally NH, Abd Eltawab MM, et al. Polarity and steric effect of the lateral substituent on the mesophase behaviour of some newly prepared liquid crystals. Liq Cryst. 2015;42:1351–1369.
  • Ahmed H, Saad G. Mesophase behaviour of laterally di-fluoro-substituted four-ring compounds. Liq Cryst. 2015;42:1765–1772.
  • Naoum M, Fahmi A, Ahmed H. Effect of the relative orientation of the two fluoro-substituents on the mesophase behavior of phenylazophenyl benzoates. Mol Cryst Liq Cryst. 2012;562:43–65.
  • Naoum M, Fahmi A, Ahmed H. Liquid crystalline behaviour of model compounds di-laterally substituted with different polar groups. Liq Cryst. 2011;38:511–519.
  • Naoum M, Ahmed H. Effect of dipole moment and conformation on the mesophase behavior of di-laterally substituted phenylazophenyl benzoate liquid crystals. Thermochim Acta. 2011;521:202–210.
  • Naoum M, Mohammady S, Ahmed H. Lateral protrusion and mesophase behaviour in pure and mixed states of model compounds of the type 4-(4′-substituted phenylazo)-2-(or 3-) methyl phenyl-4ʹ-alkoxy benzoates. Liq Cryst. 2010;37:1245–1257.
  • K- C. Crystal structure, hydrogen-bonding properties, and DFT studies of 2-((2-(2-hydroxyphenyl) benzo [d] thiazol-6-yl) methylene) malononitrile. Mol Cryst Liq Cryst. 2015;623:285–296.
  • Shoji M, Tanaka F. Theoretical study of hydrogen-bonded supramolecular liquid crystals. Macromolecules. 2002;35:7460–7472.
  • Sundaram S, Jayaprakasam R, Dhandapani M, et al. Theoretical (DFT) and experimental studies on multiple hydrogen bonded liquid crystals comprising between aliphatic and aromatic acids. J Mol Liq. 2017;243:14–21.
  • Hagar M, Ahmed H, Alhaddadd O. DFT calculations and mesophase study of Coumarin esters and its azoesters. Crystals. 2018;8:359.
  • Hagar M, Soliman SM, Ibid F, et al. Quinazolin-4-yl-sulfanylacetyl-hydrazone derivatives; synthesis, molecular structure and electronic properties. J Mol Struct. 2013;1049:177–188.
  • Soliman SM, Hagar M, Ibid F, et al. Experimental and theoretical spectroscopic studies, HOMO–LUMO, NBO analyses and thione–thiol tautomerism of a new hybrid of 1, 3, 4-oxadiazole-thione with quinazolin-4-one. Spectrochim Acta A Mol Biomol Spectrosc. 2015;145:270–279.
  • Hagar M, Soliman SM, Ibid F, et al. Synthesis, molecular structure and spectroscopic studies of some new quinazolin-4 (3H)-one derivatives; an account on the N-versus S-alkylation. J Mol Struct. 2016;1108:667–679.
  • Aboelnaga A, Hagar M, Soliman SM. Ultrasonic synthesis, molecular structure and mechanistic study of 1, 3-dipolar cycloaddition reaction of 1-alkynylpyridinium-3-olate and acetylene derivatives. Molecules. 2016;21:848.
  • Paterson DA, Gao M, Kim Y-K, et al. Understanding the twist-bend nematic phase: the characterisation of 1-(4-cyanobiphenyl-4′-yloxy)-6-(4-cyanobiphenyl-4′-yl) hexane (CB6OCB) and comparison with CB7CB. Soft Matter. 2016;12:6827–6840.
  • Martinez-Felipe A, Cook AG, Abberley JP, et al. An FT-IR spectroscopic study of the role of hydrogen bonding in the formation of liquid crystallinity for mixtures containing bipyridines and 4-pentoxybenzoic acid. RSC Adv. 2016;6:108164–108179.
  • Hagar M, Ahmed H, Saad G. Synthesis and mesophase behaviour of Schiff base/ester 4-(arylideneamino) phenyl-4 ″-alkoxy benzoates and their binary mixtures. J Mol Liq. 2019;273:266–273.
  • Chen R, An Z, Wang W, et al. Lateral substituent effects on UV stability of high-birefringence liquid crystals with the diaryl-diacetylene core: DFT/TD-DFT study. Liq Cryst. 2017;44:1515–1524.
  • Naoum MM, Fahmi AA, Alaasar MA, et al. Supramolecular liquid crystals in binary and ternary systems. Thermochim Acta. 2011;517:63–73.
  • Naoum MM, Fahmi AA, Mohammady SZ, et al. Effect of lateral substitution on supramolecular liquid crystal associates induced by hydrogen-bonding interactions between 4-(4′-pyridylazo-3-methylphenyl)-4′′-alkoxy benzoates and 4-substituted benzoic acids. Liq Cryst. 2010;37:475–486.
  • Naoum M, Fahmi A, Alaasar M. Supramolecular hydrogen-bonded liquid crystals formed from 4-(4′-pyridylazophenyl)-4 ″-alkoxy benzoates and 4-substituted benzoic acids. Mol Cryst Liq Cryst. 2008;487:74–91.
  • Alaasar M. Azobenzene-containing bent-core liquid crystals: an overview. Liq Cryst. 2016;43:2208–2243.
  • Senyuk B, Wonderly H, Mathews M, et al. Surface alignment, anchoring transitions, optical properties, and topological defects in the nematic phase of thermotropic bent-core liquid crystal A131. Phys Rev E. 2010;82:041711.
  • Frisch M, Trucks G, Schlegel HB, et al. Gaussian 09, revision a. 02. Wallingford (CT): Gaussian. Inc; 2009. p. 200.
  • Dennington R, Keith T, Millam J. 2009. GaussView, version 5. Semichem Inc., Shawnee Mission.
  • Goodby JW. Free volume, molecular grains, self-organisation, and anisotropic entropy: machining materials. Liq Cryst. 2017;44:1755–1763.
  • Singh S, Dunmur DA. 2002. Liquid crystals: fundamentals: world scientific. World Scientific Publishing Co. Pte. Ltd., London, pp. 92–277.
  • Thaker B, Kanojiya J, Tandel R. Effects of different terminal substituents on the mesomorphic behavior of some azo-schiff base and azo-ester-based liquid crystals. Mol Cryst Liq Cryst. 2010;528:120–137.
  • Gray GW. (Ed.).Molecular structure and the properties of liquid crystals. London, UK: Academic press, Inc., 1962.
  • Luckhurst G. and Gray GW. (Eds.). The molecular physics of liquid crystals. London, UK: Academic Press; 1979.
  • Yeap G-Y, Lee H-C, Mahmood WAK, et al. Synthesis, thermal and optical behaviour of non-symmetric liquid crystal dimers α-(4-benzylidene-substituted-aniline-4′-oxy)-ω-[pentyl-4-(4′-phenyl) benzoateoxy] hexane. Phase Transitions. 2011;84:29–37.
  • Imrie CT, Taylor L. The preparation and properties of low molar mass liquid crystals possessing lateral alkyl chains. Liq Cryst. 1989;6:1–10.
  • Imrie CT. Laterally substituted dimeric liquid crystals. Liq Cryst. 1989;6:391–396.

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