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Articles

Liquid crystalline benzothiophenes. Part 3: 2,4- and 2,7-disubstituted benzothiophenes

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Pages 839-852 | Received 17 Dec 2015, Accepted 19 Jan 2016, Published online: 16 Feb 2016

References

  • Perepichka IF, Perepicha DF, editors. Handbook of thiophene-based materials. Chichester: John Wiley & Sons; 2009.
  • Iino H, Hanna J. Availability of liquid crystallinity in solution processing for polycrystalline thin films. Adv Mater. 2011;23:1748–1751. doi:10.1002/adma.201004474.
  • Iino H, Kobori T, Hanna J. Improved thermal stability in organic FET fabricated with a soluble BTBT derivative. J Non-Crystall Solids. 2012;358:2516–2519. doi:10.1016/j.jnoncrysol.2012.03.021.
  • Hanna J, Ohno A, Iino H. Charge carrier transport in liquid crystals. Thin Solid Films. 2014;554:58–63. doi:10.1016/j.tsf.2013.10.051.
  • Seed A. Synthesis of self-organizing mesogenic materials containing a sulfur-based five-membered heterocyclic core. Chem Soc Rev. 2007;36:2046–2069. doi:10.1039/b612666a.
  • Campbell NL, Duffy WL, Thomas GI, et al. Nematic 2,5-disubstituted thiophenes. J Mater Chem. 2002;12:2706–2721. doi:10.1039/b202073b.
  • Seed AJ, Toyne KJ, Goodby JW. Synthesis of some 2,4- and 2,5-disubstituted thiophene systems and the effect of the pattern of substitution on the refractive indexes, optical anisotropies, polarizabilities and order parameters in comparison with those of the parent biphenyl and dithienyl systems. J Mater Chem. 1995;5:653–661.
  • Kurfürst M, Kozmík V, Svoboda J, et al. Liquid crystalline benzothiophene derivatives. Liq Cryst. 2008;35:21–31. doi:10.1080/02678290701743019.
  • Kozmík V, Henke A, Řehová L, et al. Liquid crystalline benzothiophene derivatives. Part 2: 2,5-disubstituted benzothiophenes. Liq Cryst. 2011;38:1245–1261. doi:10.1080/02678292.2011.605177.
  • Kovářová A, Svoboda J, Novotná V, et al. [2]Benzothiophene bent-shaped liquid crystals. Liq Cryst. 2010;37:1501–1513. doi:10.1080/02678292.2010.530299.
  • Majumdar KC, Mondal S, Ghosh T. Synthesis and mesomorphic behavior of novel liquid-crystalline thiophene derivatives. Mol Cryst Liq Cryst. 2010;524:17–25. doi:10.1080/15421400903568112.
  • Matharu AS, Karadakov PB, Cowling SJ, et al. Exploring the mesomorphic potential of 2,4-disubstituted thiophenes: a structure–property study. Liq Cryst. 2011;38:207–232. doi:10.1080/02678292.2010.539786.
  • Thaker BT, Patel BS, Dhimmar YT, et al. Synthesis, characterization and mesomorphic properties of new rod-like thiophene based liquid crystals. Mol Cryst Liq Cryst. 2012;562:98–113. doi:10.1080/10426507.2012.673943.
  • Han J, Wang Q, Chang X-Y, et al. Fluorescent liquid crystalline compounds with 1,3,4-oxadiazole and benzo[b]thiophene units. Liq Cryst. 2012;39:669–674. doi:10.1080/02678292.2012.671966.
  • Reddy MK, Reddy KS, Prakash M, et al. Synthesis and characterization of two phenyl ring core-based thiophene mesogens. Mol Cryst Liq Cryst. 2013;582:1–14. doi:10.1080/15421406.2013.790635.
  • Gipson RM, Sampson P, Seed AJ. The synthesis and mesogenic behaviour of the first series of low molar mass thieno[3,2-b]thiophene-2-carboxylate ester-based mesogens. Liq Cryst. 2010;37:101–108. doi:10.1080/02678290903390965.
  • Dong J, Kawabata K, Seino T, et al. Synthesis and characterisation of thieno[3,2-b]thiophene-based linear shaped liquid crystals. Liq Cryst. 2013;40:1455–1465. doi:10.1080/02678292.2013.835453.
  • 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. doi:10.1039/c3tc32211d.
  • Kovářová A, Kohout M, Svoboda J, et al. New liquid crystal based on 2-phenylthiophene central core. Liq Cryst. 2014;41:1703–1718. doi:10.1080/02678292.2014.949887.
  • Folcia CL, Ortega J, Etxebarria J, et al. Spontaneous and field-induced mesomorphism of a silyl-terminated bent-core liquid crystal as determined from second-harmonic generation and resonant X-ray scattering. Soft Matter. 2014;10:196–205. doi:10.1039/C3SM51277K.
  • Kozmík V, Polášek P, Seidler A, et al. The effect of a thiophene ring in the outer position on mesomorphic properties of the bent-shaped liquid crystals. J Mater Chem. 2010;20:7430–7435. doi:10.1039/c0jm00375a.
  • Yasuda T, Shimizu T, Liu F, et al. Electro-functional octupolar π-conjugated columnar liquid crystals. J Am Chem Soc. 2011;133:13437–13444. doi:10.1021/ja2035255.
  • Zhang L, Hughes DL, Cammidge AN. Discotic triphenylene twins linked through thiophene bridges: controlling nematic behavior in an intriguing class of functional organic materials. J Org Chem. 2012;77:4288–4297. doi:10.1021/jo3002886.
  • Lincker F, Heinrich B, De Bettignies R, et al. Synthesis, liquid crystalline behaviour, and photovoltaic applications of fluorenone core donor-acceptor-donor п-conjugated molecules end-capped with dendritic oligo(thiophene)s. J Mater Chem. 2011;21:5238–5247. doi:10.1039/c0jm02437f.
  • Baklar M, Barard S, Sparrowe D, et al. Bulk charge transport in liquid crystalline polymer semiconductors based on poly(2,5-bis(3-alkylthiophen-2-yl)thieno[3,2-b]thiophene). Polymer Chem. 2010;1:1448–1452. doi:10.1039/c0py00056f.
  • Wang A, Kawabata K, Goto H. Synthesis of isothianaphthene (ITN) and 3,4-ethylenedioxy-thiophene (EDOT)-based low band-gap liquid crystalline conjugated polymers. Materials. 2013;6:2218–2228. doi:10.3390/ma6062218.
  • Watanabe M, Kijima M. Smectic-phase-induced interdigitated orientation of polythiophenes bearing phenylnaphthalene mesogens. Liq Cryst. 2014;41:897–907. doi:10.1080/02678292.2014.891766.
  • Link DR, Natale G, Shao R, et al. Spontaneous formation of macroscopic chiral domains in a fluid smectic phase of achiral molecules. Science. 1997;278:1924–1927. doi:10.1126/science.278.5345.1924.
  • Weissflog W, Naumann G, Kosata B, et al. Ten isomeric five-ring bent-core mesogens: the influence of the direction of the carboxyl connecting groups on the mesophase behaviour. J Mater Chem. 2005;15:4328–4337. doi:10.1039/b508488a.
  • Kohout M, Svoboda J, Novotná V, et al. Non-symmetrical bent-shaped liquid crystals based on a laterally substituted naphthalene central core with four ester groups. Liq Cryst. 2011;38:1099–1110. doi:10.1080/02678292.2011.596949.
  • Szydlowska J, Mieczkowski J, Matraszek J, et al. Bent-core liquid crystals forming two- and three-dimensional modulated structures. Phys Rev E. 2003;67:031702. doi:10.1103/PhysRevE.67.031702.
  • Gorecka E, Vaupotić N, Pociecha D, et al. Switching mechanism in polar columnar mesophases made of bent-core molecules. Chem Phys Chem. 2005;6:1087–1093.
  • Gorecka E, Vaupotič N, Pociecha D. Electron density modulations in columnar banana phases. Chem Mater. 2007;19:3027–3031. doi:10.1021/cm0625575.
  • Coleman DA, Jones CD, Nakata M, et al. Polarization splay as the origin of modulation in the B1 and B7 smectic phases of bent-core molecules. Phys Rev E. 2008;77:021703. doi:10.1103/PhysRevE.77.021703.
  • Amarantha Reddy R, Tschierske C. Bent-core liquid crystals: polar order, superstructural chirality and spontaneous desymmetrisation in soft matter systems. J Mater Chem. 2006;16:907–961. doi:10.1039/B504400F.
  • Hinkel LE, Ayling EE, Morgan WH. Substituted aromatic aldehydes in Hantzsch’s pyridine condensation. Part III. Nitromethoxy- and nitrohydroxy-benzaldehydes. J Chem Soc. 1932;1112–1118. doi:10.1039/jr9320001112.
  • Bridges AJ, Lee A, Maduakor EC, et al. Fluorine as an ortho-directing group in aromatic metalation: a two-step preparation of substituted benzo[b]thiophene-2-carboxylates. Tetrahedron Let. 1992;33:7499–7502. doi:10.1016/S0040-4039(00)60806-7.
  • Kohout M, Svoboda J, Novotná V, et al. A nematic-polar columnar phase sequence in new bent-shaped liquid crystals based on a 7-hydroxynaphthalene-2-carboxylic acid core. J Mater Chem. 2009;19:3153–3160. doi:10.1039/b821234a.
  • Bubnov A, Hamplova V, Kaspar M, et al. New ferroelectric liquid crystalline substances with lateral groups in the core. Mol Cryst Liq Cryst A. 2001;366:547–556. doi:10.1080/10587250108023995.
  • 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. doi:10.1080/02678292.2012.678396.
  • Rahman LKA, Scrowston RM. 7-Substituted benzo[b]thiophenes and 1,2-benzisothiazoles. Part 1. Hydroxy- or methoxy-derivatives. J Chem Soc, Perkin Trans 1. 1983;2973–2977. doi:10.1039/p19830002973.

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