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Original Articles

Molecular symmetry effects on the stability of highly ordered smectic phases

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Pages 76-85 | Received 14 Feb 2018, Accepted 29 Apr 2018, Published online: 22 May 2018

References

  • Hsiao Y-C, E-R Y, Lee W. Advanced color-reflective dual-frequency cholesteric liquid crystal displays and the driving matrix. Mol Cryst Liq Cryst. 2017;644:12–18.
  • Gupta RK, Manjuladevi V, Karthik C, et al. Thin films of discotic liquid crystals and their applications. Liq Cryst. 2016;43:2079–2091.
  • Raynes P. TN, STN, and guest–host liquid crystal display devices. Goodby JW, Collings PJ, Kato T, et al., editors. Handbook of liquid crystals. 2nd ed. Weinheim:Wiley-VCH Verlag GmbH & Co. KGaA; 2014. p.3–20.
  • Hong H. In-plane switching display devices. Goodby JW, Collings PJ, Kato T, et al., editors. Handbook of liquid crystals. 2nd ed. Weinheim:Wiley-VCH Verlag GmbH & Co. KGaA; 2014. p.21–40.
  • He Q, Lei H, Luo S, et al. Liquid crystal biosensor for detecting ischemia modified albumin. Res Chem Intermed. 2017;43:353–360.
  • Setia S, Sidiq S, De J, et al. Applications of liquid crystals in biosensing and organic light-emitting devices: future aspects. Liq Cryst. 2016;43:2009–2050.
  • Gleeson HF. Thermography using liquid crystals. Goodby JW, Collings PJ, Kato T, et al., editors. Handbook of liquid crystals. 2nd ed. Weinheim:Wiley-VCH Verlag GmbH & Co. KGaA; 2014. p.517–538.
  • Chapran M, Angioni E, Findlay NJ, et al. An ambipolar BODIPY derivative for a white exciplex OLED and cholesteric liquid crystal laser toward multifunctional devices. ACS Appl Mater Interfaces. 2017;9:4750–4757.
  • Chen C-W, Huang H-P, Jau H-C, et al. Polarization-asymmetric bidirectional random laser emission from a twisted nematic liquid crystal. J Appl Phys. 2017;121:33102.
  • Zhao K-Q, Du J-Q, Long X-H, et al. Design of Janus triphenylene mesogens: facile synthesis, mesomorphism, photoluminescence, and semiconductivity. Dyes Pigments. 2017;143:252–260.
  • Volpi R, Camilo ACS, Filho DA DA S, et al. Modelling charge transport of discotic liquid-crystalline triindoles: the role of peripheral substitution. Phys Chem Chem Phys. 2017;19:24202–24208.
  • Pisula W, Müllen K. Discotic liquid crystals as organic semiconductors. Goodby JW, Collings PJ, Kato T, et al., editors. Handbook of liquid crystals. 2nd ed. Weinheim:Wiley-VCH Verlag GmbH & Co. KGaA; 2014. p.627–674.
  • Voisin E, Williams VE. The impact of molecular symmetry and shape on the stability of discotic liquid crystals. Can J Chem. 2017;1–7. DOI:10.1139/cjc-2017-0317
  • Voisin E, Williams VE. Side-chain shuffling: regioselective synthesis of mixed tail discotic mesogens. RSC Adv. 2016;6:11262–11265.
  • Voisin E, Johan Foster E, Rakotomalala M, et al. Effects of symmetry on the stability of columnar liquid crystals. Chem Mater. 2009;21:3251–3261.
  • Foster EJ, Babuin J, Nguyen N, et al. Synthesis of unsymmetrical dibenzoquinoxaline discotic mesogens. Chem Commun. 2004;18:2052–2053.
  • Iino H, Hanna J. Liquid crystalline organic semiconductors for organic transistor applications. Polym J. 2017;49:23–30.
  • Iino H, Usui T, Hanna J. Liquid crystals for organic thin-film transistors. Nat Commun. 2015;6:6828.
  • Funahashi M, Yasuda T, Kato T. Liquid crystal semiconductors: oligothiophene and related materials. Goodby JW, Collings PJ, Kato T, et al., editors. Handbook of liquid crystals. 2nd ed. Weinheim:Wiley-VCH Verlag GmbH & Co. KGaA; 2014. p.675–708.
  • Ruiz C, Pandey UK, Termine R, et al. Mobility versus alignment of a semiconducting π-extended discotic liquid-crystalline triindole. ACS Appl Mater Interfaces. 2016;8:26964–26971.
  • Bashir A, Heck A, Narita A, et al. Charge carrier mobilities in organic semiconductors: crystal engineering and the importance of molecular contacts. Phys Chem Chem Phys. 2015;17:21988–21996.
  • Iino H, Hanna J-I. Liquid crystal and crystal structures of a phenyl-benzothienobenzothiophene derivative. Mol Cryst Liq Cryst. 2017;647:37–43.
  • Hanna J, Ohno A, Iino H. Charge carrier transport in liquid crystals. Thin Solid Films. 2014;554:58–63.
  • Tokunaga K, Takayashiki Y, Iino H, et al. One-dimensional to three-dimensional electronic conduction in liquid crystalline mesophases. Mol Cryst Liq Cryst. 2009;510:1384–1392.
  • Chen G-H, Springer J, Thyen W, et al. Surface phenomena of liquid crystalline substances. Mol Cryst Liq Cryst Sci Technol Sect Mol Cryst Liq Cryst. 1998;325:99–116.
  • Kubo TSK. Synthesis and mesomorphic properties of liquid crystals with a 5,5ʹ-bitropolone skelton. Chem Lett. 2001;7:690–691.
  • Murashige R, Hayashi Y, Ohmori S, et al. Comparisons of O-acylation and Friedel–Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: effective synthesis of optically active homotyrosines. Tetrahedron. 2011;67:641–649.
  • Goodby JW. Structures and properties of smectic liquid crystals. Goodby JW, Collings PJ, Kato T, et al., editors. Handbook of liquid crystals. 2nd ed. Weinheim:Wiley-VCH Verlag GmbH & Co. KGaA; 2014. p.43–68.
  • Getmanenko YA, Kang S-W, Shakya N, et al. Bis(5-alkylthiophen-2-yl)arene liquid crystals as molecular semiconductors. J Mater Chem C. 2014;2:2600–2611.
  • Getmanenko YA, Kang S-W, Shakya N, et al. 5,5′-Bis-(alkylpyridinyl)-2,2′-bithiophenes: synthesis, liquid crystalline behaviour and charge transport. J Mater Chem C. 2013;2:256–271.
  • Dierking I. Ch. 9 - The hexatic phases. In: Textures of liquid crystals. 1st ed. Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA; 2003. p. 135–140.
  • The Sm F and Sm I phases have similar structures that vary only in the orientation of the tilt of the molecules (towards the side of the hexagon for Sm F and towards the apex for Sm I) making them virtually indistinguishable without well-aligned XRD samples. The same goes for the respective analogous soft crystalline phases; G/J and H/K, commonly observed at lower temperatures.
  • Martinelli E, Paoli F, Gallot B, et al. Mesophase structure of low-wetting liquid crystalline polyacrylates with new perfluoroalkyl benzoate side groups. J Polym Sci Part Polym Chem. 2010;48:4128–4139.
  • Gallot B, Galli G, Ceccanti A, et al. X-ray studies on the smectic polymorphism of chiral polysiloxanes with a sulfide substituent. Polymer. 1999;40:2561–2568.
  • Gane PAC, Leadbetter AJ, Wrighton PG. Structure and correlations in smectic B, F and I phases. Mol Cryst Liq Cryst. 1981;66:247–266.
  • Gane PAC, Leadbetter AJ, Moussa F, et al. Structural correlations in smectic-F and smectic-I phases. Physical Review A. 1981;24:2694–2700.
  • Carnelley T XIII. Chemical symmetry, or the influence of atomic arrangement on the physical properties of compounds. Lond Edinb Dublin Philos Mag J Sci. 1882;13:112–130.
  • Carnelley T XXI. Chemical symmetry, or the influence of atomic arrangement on the physical properties of compounds. Lond Edinb Dublin Philos Mag J Sci. 1882;13:180–193.
  • Yalkowsky SH. Carnelley’s rule and the prediction of melting point. J Pharm Sci. 2014;103:2629–2634.
  • Dziubek KF, Katrusiak A. Structure-melting relations in isomeric dibromobenzenes. Acta Crystallogr Sect B Struct Sci Cryst Eng Mater. 2014;70:492–497.
  • Brown RJC, Brown RFC. Melting point and molecular symmetry. J Chem Educ. 2000;77:724–731.
  • Goodby JW. Free volume, molecular grains, self-organisation, and anisotropic entropy: machining materials. Liq Cryst. 2017;44:1755–1763.
  • Ishikawa M, Hashimoto Y. Improvement in aqueous solubility in small molecule drug discovery programs by disruption of molecular planarity and symmetry. J Med Chem. 2011;54:1539–1554.
  • Pinal R. Effect of molecular symmetry on melting temperature and solubility. Org Biomol Chem. 2004;2:2692–2699.
  • Lavigueur C, Foster EJ, Williams VE. A simple and inexpensive capillary furnace for variable-temperature X-ray diffraction. J Appl Crystallogr. 2008;41:214–216.

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