Abstract
Liquid crystalline molecules are extensively used for technological applications such as liquid crystal displays, and there is a great deal of research underway in various fields exploring other uses. The carbon–carbon bond-forming cross-coupling reactions can provide innovative synthetic methods for new liquid crystalline molecules with novel physical properties. Moreover, the organic molecules synthesized with the cross-coupling reactions may be used in new areas such as organic electroluminescence (EL) and thin film transistors (TFT).
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References
Reinitzer F (1888) Beiträge zur kenntniss des cholesterins. Monatsh Chem 9:421–441
de Gennes PG (1975) The physics of liquid crystals. Clarendon Press, Oxford
Chandrasekhar S (1977) Liquid crystals. Cambridge University Press, Cambridge
Ciferri A, Krigbaum WR, Meyer RB (1982) Polymer liquid crystals. Academic Press, New York
Chapoy LL (1985) Recent advances in liquid crystalline polymers. Elsevier Applied Science Publishers, London
Blumstein A (1985) Polymeric liquid crystals. Plenum Press, New York
Gray GW (1987) Thermotropic liquid crystal. Wiley, New York
Demus D, Goodby J, Gray GW, Spiess HW, Vill V (1998) Handbook of liquid crystals, vols. 1–4. Wiley, Weinheim
Goodby J (2007) Liquid crystals (theme issue). Chem Soc Rev 36:1845–2128
Pakiari AH, Aazami SM, Ghanadzadeh A (2008) Electronic interactions of typical liquid crystal molecules with typical contacted species generated from the surface of different materials. J Mol Liq 139:8–13
Kumar S, Varshney K (2000) A room-temperature discotic nematic liquid crystal. Angew Chem Int Ed 39:3140–3142
Kumar S, Bisoyi HK (2010) Discotic nematic liquid crystals: science and technology. Chem Soc Rev 39:264–285
Adam D, Closs F, Frey T, Funhoff D, Harrer D, Ringsdorf J, Schuhmacher P, Siemensmeyer K (1993) Transient photoconductivity in a discotic liquid crystal. Phys Rev Lett 70:457–460
Ponomarenko S, Kirchmeyer S (2003) Synthesis and thermal behaviour of α, α’-didecyloligothiophenes. J Mater Chem 13:197–202
Cheng XH, Dong X, Zheng T, Ye H, Wei GH (2008) Synthesis and mesomorphic behavior of 3-alkyl-2,5- bis[p-(hexa-2,4-dienoyloxy)phenyl]-thiophene derivatives. Chin J Chem 26:146–149
Meng Q, Sun XH, Lu Z, Xia PF, Shi Z, Chen D, Wong MS, Wakim S, Lu J, Baribeau JM, Tao Y (2009) Syntheses, phase behavior, supramolecular chirality, and field-effect carrier mobility of asymmetrically end-capped mesogenic oligothiophenes. Chem Eur J 15:3474–3487
Babudri F, Cicco SR, Farinola GM, Naso F (1996) Synthesis, characterization and properties of a soluble polymer with a poly(phenylenevinylene) structure. Macromol Rapid Commun 17:905–911
Toudic F, Heynderickx A, Plé N, Turck A, Quéguiner G (2003) Regioselective synthesis and metallation of tributylstannylfluoropyrazines. Application to the synthesis of some new fluorinated liquid crystals diazines. Part 34. Tetrahedron 59:6375–6384
Choi JH, Cho DW, Jin SH, Yoon UC (2007) Synthesis and properties of hexyl end-capped thiophene oligomers containing anthracene moiety in the center. Bull Korean Chem Soc 28:1175–1182
Getmanenko YA, Twieg RJ (2008) Unprecedented Negishi coupling at C-Br in the presence of a stannyl group as a convenient approach to pyridinylstannanes and their application in liquid crystal synthesis. J Org Chem 73:830–839
Hsu HF, Kuo CH, Chen CF, Lin YH, Huang LY, Chen CH, Cheng KC, Chen HH (2004) Synthesis and mesomorphic properties of multiynylthiophenes: 2,3,4,5-tetrakis(4-alkoxyphenylethynyl)thiophenes and 2,3,5-tris(4-alkoxyphenylethynyl)thiophenes. Chem Mater 16:2379–2385
Luo J, Zhao B, Shao J, Lim KA, Chan HSO, Chi C (2009) Room-temperature discotic liquid crystals based on oligothiophenes-attached and fused triazatruxenes. J Mater Chem 19:8327–8334
Hird M, Seed AJ, Toyne KJ, Goodby JW, Grayb GW, McDonnell DG (1993) Synthesis, transition temperatures and optical anisotropy of some isothiocyanato-substituted biphenyls. J Mater Chem 3:851–859
Liu P, Yan M, He R (2010) Bis(imino)pyridine palladium(II) complexes as efficient catalysts for the Suzuki–Miyaura reaction in water. Appl Organomet Chem 24:131–134
Liu P, Feng X, He R (2010) Salen and half-salen palladium(II) complexes: synthesis, characterization and catalytic activity toward Suzuki–Miyaura reaction. Tetrahedron 66:631–636
Kiryanov AA, Sampson P, Seed AJ (2001) Synthesis and mesomorphic properties of 1,1-difluoroalkyl-substituted biphenylthienyl and terphenyl liquid crystals. A comparative study of mesomorphic behavior relative to alkyl, alkoxy and alkanoyl analogs. J Mater Chem 11:3068–3077
Vlachos P, Kelly SM, Mansoor B, O’Neill M (2002) Electron-transporting and photopolymerisable liquid crystals. Chem Commun, 874–875
Larios-LĂłpez L, Navarro-RodrĂguez D, Donnio B, Guillon D (2006) Synthesis and liquid-crystalline properties of bromoalkyloxy-substituted terphenylenes. Chem Lett 35:652–653
Bhalla V, Singh H, Kumar M (2010) Facile cyclization of terphenyl to triphenylene: A new chemodosimeter for fluoride ions. Org Lett 12:628–631
Schultz A, Laschat S, Saipa A, Gieβelmann F, Nimtz M, Schulte JL, Baro A, Miehlich B (2004) Columnar liquid crystals with a central crown ether unit. Adv Funct Mater 14:163–168
Jin L, Li Y, Ma J, Li Q (2010) Synthesis of novel thermally reversible photochromic axially chiral spirooxazines. Org Lett 12:3552–3555
Matsui A, Funahashi M, Tsuji T, Kato T (2010) High hole mobility for a side-chain liquid-crystalline smectic polysiloxane exhibiting a nanosegregated structure with a terthiophene moiety. Chem Eur J 16:13465–13472
Lim E, Lee S, Lee KK (2011) Improved photovoltaic performance of P3HT: PCBM cells by addition of a low band-gap oligomer. Chem Commun, 914–916
Yang GZ, Chen XL, Wang LM, Shi JG, Li CZ, Liu T (2009) Synthesis and characterization of fluorene-based rod-coil liquid crystal polymers. Polym Adv Technol 20:104–110
Yao K, Chen Y, Chen L, Kong H, Zhou W, Li F, He X, Wei Y (2010) Photoluminescent, liquid-crystalline, and electrochemical properties of para-phenylene-based alternating conjugated copolymers. J Polym Sci Part A Polym Chem 48:434–442
Kouwer PHJ, Jager WF, Mijs WJ, Picken SJ (2003) Specific interactions in discotic liquid crystals. J Mater Chem 13:458–469
Nishihara Y, Ikegashira K, Hirabayashi K, Ando J, Mori A, Hiyama T (2000) Coupling reactions of alkynylsilanes mediated by a Cu(I) salt: novel syntheses of conjugate diynes and disubstituted ethynes. J Org Chem 65:1780–1787
Ito S, Inabe H, Morita N, Ohta K, Kitamura T, Imafuku K (2003) Synthesis of poly(6-azulenylethynyl)benzene derivatives as a multielectron redox system with liquid crystalline behavior. J Am Chem Soc 125:1669–1680
Wu J, Watson MD, Zhang L, Wang Z, Müllen K (2003) Hexakis(4-iodophenyl)-peri-hexabenzocoronene- a versatile building block for highly ordered discotic liquid crystalline materials. J Am Chem Soc 126:177–186
Zhaohui W, Watson MD, Jishan W, Müllen K (2004) Partially stripped insulated nanowires: a lightly substituted hexa-perihexabenzo-coronene-based columnar liquid crystal. Chem Commun, 336–337
Vasconcelos UB, Merlo AA (2006) Synthesis and mesomorphic behavior of new N-heterotolane liquid crystals containing a naphthyl-pyridyl framework. Synthesis, 1141–1147
Hennrich G, Ortiz PD, Cavero E, Hanes RE, Serrano JL (2008) Biphenyl-based disc- vs. rod-shaped phenylacetylenes: Mesomorphism and electronic properties. Eur J Org Chem, 4575–4579
Achelle S, Plé N, Kreher D, Mathevet F, Turck A, Attias AJ (2008) Oligomers containing ethynylpyridazine moieties: Synthesis, fluorescence and liquid crystalline properties. Diazines 50. Heterocycles 75:357–374
Tannaci JF, Noji M, McBee JL, Tilley TD (2008) 9,10-Disubstituted octafluoroanthracene derivatives via palladium-catalyzed cross-coupling. J Org Chem 73:7895–7900
Gallardo H, Cristiano R, Vieira AA, Rawn F, Srivastava RM (2008) Sonogashira coupling applied in the synthesis of 1,2,4-oxadiazole-based nonsymmetrical liquid crystals. Synthesis, 605–609
Hongyong S, Ruimao H, Qingwei Z, Jianli Z, Xiao L, Qiming Z (2010) An improved practical Pd/C-catalyzed Sonogashira cross-coupling reaction for the synthesis of liquid crystals of trans-cyclohexyltolans. Appl Organomet Chem 24:473–476
Vega LD, Ortiz PD, Hennrich G, Omenat A, Tejedor RM, Barberá J, Gómez-Lor B, Serrano JL (2010) Chiral biphenylacetylene smectic liquid crystals. J Phys Chem B 114:4811–4815
Majumdar KC, Mondal S, De N, Sinha RK, Pal N, Roy B (2010) Synthesis and mesomorphic behaviour of new discotic liquid crystalline compounds containing triphenylamine as a core moiety via Sonogashira coupling. Tetrahedron Lett 51:521–524
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Chang, NH., Kinoshita, M., Nishihara, Y. (2013). Liquid Crystals. In: Nishihara, Y. (eds) Applied Cross-Coupling Reactions. Lecture Notes in Chemistry, vol 80. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-32368-3_5
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DOI: https://doi.org/10.1007/978-3-642-32368-3_5
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