Synthesis of new wide nematic diaryl-diacetylenes containing thiophene-based heteromonocyclic and heterobicyclic structures, and their birefringence properties

References

• Contoret AEA, Farrar SR, O’Neill M, Nicholls JE, Richards GJ, Kelly SM, Hall AW. The photopolymerization and cross-linking of electroluminescent liquid crystals containing methacrylate and diene photopolymerizable end groups for multilayer organic light-emitting diodes. Chem Mater. 2002;14:1477–1487. doi:10.1021/cm011111f
   Web of Science ®Google Scholar
• Woon KL, Aldred MP, Vlachos P, Mehl GH, Stirner T, Kelly SM, O’Neill M. Electronic charge transport in extended nematic liquid crystals. Chem Mater. 2006;18:2311–2317. doi:10.1021/cm0601335
   Web of Science ®Google Scholar
• Radhakrishnan S, Somanathan N, Narasimhaswamy T. Structure–property studies and orientation effects of polythiophenes containing mesogenic side chains. J Polym Sci B: Polym Phys. 2008;46:1463–1477. doi:10.1002/polb.21482
   Web of Science ®Google Scholar
• Han J, Wang Q, Chang XY, Zhu LR. 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
   Web of Science ®Google Scholar
• Aldred MP, Carrasco-Orozco M, Contoret AEA, Dong D, Farrar SR, Kelly SM, Kitney SP, Mathieson D, O’Neill M, Tsoi WC, Vlachos P. Organic electroluminescence using polymer networks from smectic liquid crystals. Liq Cryst. 2006;33:459–467. doi:10.1080/02678290500487073
   Web of Science ®Google Scholar
• Asai K, Konishi G, Nakajima Y, Kawauchi S, Ozawa F, Mizuno K. Enhanced absorption and fluorescence efficiency of silylethynyl-functionalized oligothiophenes and thieno[3,2–b]thiopahene. J Organomet Chem. 2011;696:1266–1271. doi:10.1016/j.jorganchem.2010.10.044
   Web of Science ®Google Scholar
• Li F, Chen W, Chen Y. Mesogen induced self-assembly for hybrid bulk heterojunction solar cells based on a liquid crystal D–A copolymer and ZnO nanocrystals. J Mater Chem. 2012;22:6259–6266. doi:10.1039/c2jm16853g
   Web of Science ®Google Scholar
• Lincker F, Heinrich B, Bettignies RD, Rannou P, Pécaut J, Grévin B, Pron A, Donnio B, Demadrille R. Fluorenone core donor–acceptor–donor π-conjugated molecules end-capped with dendritic oligo(thiophene)s: synthesis, liquid crystalline behaviour, and photovoltaic applications. J Mater Chem. 2011;21:5238–5247. doi:10.1039/c0jm02437f
   Web of Science ®Google Scholar
• Yao K, Chen L, Chen Y, Li F, Ren X, Wang H, Li Y. Tuning the photovoltaic parameters of thiophene-linked donor–acceptor liquid crystalline copolymers for organic photovoltaics. Polym Chem. 2012;3:710–717. doi:10.1039/c2py00523a
   Web of Science ®Google Scholar
• Li X, Chen L, Chen Y, Li F, Yao K. Photocrosslinkable liquid-crystalline polythiophenes with oriented nanostructure and stabilization for photovoltaics. Org Electron. 2012;13:104–113. doi:10.1016/j.orgel.2011.10.012
   Web of Science ®Google Scholar
• Oikawa K, Monobe H, Nakayama K, Kimoto T, Tsuchiya K, Heinrich B, Guillon D, Shimizu Y, Yokoyama M. High carrier mobility of organic field-effect transistors with a thiophene–naphthalene mesomorphic semiconductor. Adv Mater. 2007;19:1864–1868. doi:10.1002/adma.200602608
   Web of Science ®Google Scholar
• Funahashi M, Hanna J. High carrier mobility up to 0.1 cm2 V-1 s-1 at ambient temperatures in thiophene-based smectic liquid crystals. Adv Mater. 2005;17:594–598. doi:10.1002/adma.200401274
   Web of Science ®Google Scholar
• Garnier F, Hajlaoui R, El Kassmi A, Horowitz G, Laigre L, Porzio W, Armanini M, Provasoli F. Dihexylquaterthiophene, a two-dimensional liquid crystal-like organic semiconductor with high transport properties. Chem Mater. 1998;10:3334–3339. doi:10.1021/cm970704g
   Web of Science ®Google Scholar
• He B, Tian H, Yan D, Geng Y, Wang F. Novel liquid crystalline conjugated oligomers based on phenanthrene for organic thin film transistors. J Mater Chem. 2011;21:14793–14799. doi:10.1039/c1jm13086b
   Web of Science ®Google Scholar
• Janssen PGA, Pouderoijen MA, van Breemen AJJM, Herwig PT, Koeckelberghs G, Popa-Merticaru AR, Meskers SCJ, Valeton JJP, Meijer EW, Schenning APHJ. Synthesis and properties of α,ω-phenyl-capped bithiophene derivatives. J Mater Chem. 2006;16:4335–4342. doi:10.1039/b608441a
   Web of Science ®Google Scholar
• Lim E, Jung BJ, Lee J, Shim HK, Lee JI, Yang YS, Do LM. Thin-film morphologies and solution-processable field-effect transistor behavior of a fluorene−thieno[3,2-b]thiophene-based conjugated copolymer. Macromolecules. 2005;38:4531–4535. doi:10.1021/ma048128e
   Web of Science ®Google Scholar
• Mcculloch I, Heeney M, Bailey C, Genevicius K, Macdonald I, Shkunov M, Sparrowe D, Tierney S, Wagner R, Zhang W, Chabinyc ML, Kline R, Mcgehee MD, Toney MF. Liquid-crystalline semiconducting polymers with high charge-carrier mobility. Nat Mater. 2006;5:328–333. doi:10.1038/nmat1612
   PubMed Web of Science ®Google Scholar
• Funahashi M. Development of liquid-crystalline semiconductors with high carrier mobilities and their application to thin-film transistors. Polym J. 2009;41:459–469. doi:10.1295/polymj.PJ2008324
   Web of Science ®Google Scholar
• Liu P, Wu Y, Pan H, Li Y, Gardner S, Ong BS, Zhu S. Novel high-performance liquid-crystalline organic semiconductors for thin-film transistors. Chem Mater. 2009;21:2727–2732. doi:10.1021/cm900265q
   Web of Science ®Google Scholar
• Nuita M, Sakuda J, Hirai Y, Funahashi M, Kato T. Hole transport of a liquid-crystalline phenylterthiophene derivative exhibiting the nematic phase at ambient temperature. Chem Lett. 2011;40:412–413. doi:10.1246/cl.2011.412
   Web of Science ®Google Scholar
• Matsui A, Funahashi M, Tsuji T, Kato T. High hole mobility for a side-chain liquid-crystalline smectic polysiloxane exhibiting a nanosegregated structure with a terthiophene moiety. Chem Eur J. 2010;16:13465–13472. doi:10.1002/chem.200902440
   PubMed Web of Science ®Google Scholar
• Yasuda T, Shimizu T, Liu F, Ungar G, Kato T. Electro-functional octupolar π-conjugated columnar liquid crystals. J Am Chem Soc. 2011;133:13437–13444. doi:10.1021/ja2035255
   PubMed Web of Science ®Google Scholar
• Miyajima D, Araoka F, Takezoe H, Kim J, Kato K, Takata M, Aida T. Electric-field-responsive handle for large-area orientation of discotic liquid-crystalline molecules in millimeter-thick films. Angew Chem Int Ed. 2011;50:7865–7869. doi:10.1002/anie.201102472
   PubMed Web of Science ®Google Scholar
• Watanabe K, Osaka I, Yorozuya S, Akagi K. Helically π-stacked thiophene-based copolymers with circularly polarized fluorescence: high dissymmetry factors enhanced by self-ordering in chiral nematic liquid crystal phase. Chem Mater. 2012;24:1011–1024. doi:10.1021/cm2028788
   Web of Science ®Google Scholar
• Yamao T, Yamamoto K, Taniguchi Y, Miki T, Hotta S. Laser oscillation in a highly anisotropic organic crystal with a refractive index of 4.0. J Appl Phys. 2008;103:093115. doi:10.1063/1.2919710
   Web of Science ®Google Scholar
• Fukuzaki N, Higashihara T, Ando S, Ueda M. Synthesis and characterization of highly refractive polyimides derived from thiophene-containing aromatic diamines and aromatic dianhydrides. Macromolecules. 2010;43:1836–1843. doi:10.1021/ma902013y
   Web of Science ®Google Scholar
• Asai K, Konishi G, Sumi K, Mizuno K. Synthesis of silyl-functionalized oligothiophene-based polymers with bright blue light-emission and high refractive index. J Organomet Chem. 2011;696:1236–1243. doi:10.1016/j.jorganchem.2010.11.013
   Web of Science ®Google Scholar
• Nakagawa Y, Suzuki Y, Higashihara T, Ando S, Ueda M. Synthesis of highly refractive poly(phenylene thioether)s containing a binaphthyl or diphenylfluorene unit. Polym Chem. 2012;3:2531–2536. doi:10.1039/c2py20325a
   Web of Science ®Google Scholar
• An YC, Konishi G. Facile synthesis of high refractive index thiophene-containing polystyrenes. J Appl Polym Sci. 2012;124:789–795. doi:10.1002/app.35077
   Web of Science ®Google Scholar
• 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 indices, optical anisotropies, polarisabilities and order parameters in comparison with those of the parent biphenyl and dithienyl systems. J Mater Chem. 1995;5:653–661
   Web of Science ®Google Scholar
• Campbell NL, Duffy WL, Thomas GI, Wild JH, Kelly SM, Bartle K, O’Neill M, Minter V, Tuffin RP. Nematic 2,5-disubstituted thiophenes. J Mater Chem. 2002;12:2706–2721. doi:10.1039/b202073b
   Web of Science ®Google Scholar
• Brettle R, Dunmur DA, Marson CM, Piñol M, Toriyama K. New liquid-crystalline compounds based on thiophene. Chem Lett. 1992;21:613–616. doi:10.1246/cl.1992.613
   Web of Science ®Google Scholar
• Brettle R, Dunmur DA, Marson CM, Piñol M, Toriyama K. New liquid crystalline compounds based on 2-arylthiophenes and 2-(biphenyl-4-yl)thiophenes. Liq Cryst. 1993;13:515–529. doi:10.1080/02678299308026324
   Web of Science ®Google Scholar
• Kuiper S, Jager WF, Dingemans TJ, Picken SJ. Liquid crystalline properties of all symmetric p-phenylene and 2,5-thiophene pentamers. Liq Cryst. 2009;36:389–396. doi:10.1080/02678290902923410
   Web of Science ®Google Scholar
• Matharu AS, Grover C, Komitov L, Andersson G. Ferro-, ferri- and antiferro-electric behaviour in a bent-shaped mesogen. J Mater Chem. 2000;10:1303–1310. doi:10.1039/b000128g
   Web of Science ®Google Scholar
• Geese K, Prehm M, Tschierske C. Bent-core mesogens with thiophene units. J Mater Chem. 2010;20:9658–9665. doi:10.1039/c0jm01919d
   Web of Science ®Google Scholar
• Mcdonald R, Lacey D, Watson P, Cowling S, Wilson P. Synthesis and evaluation of some novel chiral heterocyclic liquid crystalline materials exhibiting ferro‐ and antiferro‐electric phases. Liq Cryst. 2005;32:319–330. doi:10.1080/02678290500033711
   Web of Science ®Google Scholar
• Cernovska K, Kosata B, Svoboda J, Novotna V, Glogarova M. Novel ferroelectric liquid crystals based on fused thieno[3,2-b]furan and thieno[3,2-b]thiophene cores. Liq Cryst. 2006;33:987–996. doi:10.1080/02678290600905404
   Web of Science ®Google Scholar
• Pintre IC, Serrano JL, Ros MB, Ortega J, Alonso I, Martínez-Perdiguero J, Folcia CL, Etxebarria J, Goc F, Amabilino DB, Puigmartí-Luis J, Gomar-Nadal E. TTF-based bent-core liquid crystals. Chem Commun. 2008;22:2523–2525. doi:10.1039/b801196f
   PubMed Web of Science ®Google Scholar
• Kozmík V, Polášek P, Seidler A, Kohout M, Svoboda J, Novotná V, Glogarová M, Pociecha D. 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
   Web of Science ®Google Scholar
• Sekine C, Konya N, Minai M,. Fujisawa K. Synthesis and properties of high birefringence liquid crystals: thiophenylacetylene and benzothiazolylacetylene derivatives. Liq Cryst. 2001;28:1361–1367. doi:10.1080/02678290110061386
   Web of Science ®Google Scholar
• Zhang Z, Zhang L, Guan X, Shen Z, Chen X, Xing G, Fan X, Zhou Q. Synthesis and properties of highly birefringent liquid crystalline materials: 2,5-bis(5-alkyl-2-butadinylthiophene-yl) styrene monomers. Liq Cryst. 2009;37:69–76. doi:10.1080/02678290903370272
   Web of Science ®Google Scholar
• Seed AJ, Toyne KJ, Goodby JW, Hird M. Synthesis, transition temperatures, and optical properties of various 2,6-disubstituted naphthalenes and related 1-benzothiophenes with butylsulfanyl and cyano or isothiocyanato terminal groups. J Mater Chem. 2000;10:2069–2080. doi:10.1039/b003818k
   Web of Science ®Google Scholar
• Seed AJ, Cross GJ, Toyne KJ, Goodby JW. Novel, highly polarizable thiophene derivatives for use in nonlinear optical applications. Liq Cryst. 2003;30:1089–1107. doi:10.1080/0267829031000154363
   Web of Science ®Google Scholar
• Seed AJ, Toyne KJ, Hird M, Goodby JW. Synthesis and mesomorphic behaviour of high polarisability materials for non-linear optical applications. Liq Cryst. 2012;39:403–414. doi:10.1080/02678292.2012.658090
   Web of Science ®Google Scholar
• Grant B. Diacetylenic liquid crystals: synthesis and preliminary characterization of 4,4′-dialkyl and 4,4′-dialkoxy derivatives of diphenyldiacetylene. Mol Cryst Liq Cryst. 1978;48:175–182. doi:10.1080/00268947808083757
   Web of Science ®Google Scholar
• Wu ST, Meng HB, Dalton LR. Diphenyl-diacetylene liquid crystals for electro-optic application. J Appl Phys. 1991;70:3013–3017. doi:10.1063/1.349331
   Web of Science ®Google Scholar
• Hudson CM, Shenoy RA, Neubert ME Petschek RG. Synthesis and mesomorphic properties of some asymmetrical pyrimidinylphenyldiacetylenes. Liq Cryst. 1999;26:241–250. doi:10.1080/026782999205380
   Web of Science ®Google Scholar
• Goto Y, Inukai T, Fujita A, Demus D. New nematics with high birefringence. Mol Cryst Liq Cryst. 1995;260:23–38. doi:10.1080/10587259508038681
   Web of Science ®Google Scholar
• Neubert ME, Keast SS, Kim JM, Miller KJ, Murray RM, Norton AG, Shenoy RA, Walsh ME, Petschek RG. The effect of replacing a benzene ring with a saturated six-membered ring on the mesomorphic properties of 4,4′-disubstituted diphenyldiacetylenes. Liq Cryst. 2004;31:175–184. doi:10.1080/0267829032000159114
   Web of Science ®Google Scholar
• Hsu HF, Lai YH, Lin SY, Lin WC, Chen JF. Impact on the mesophase transition temperatures of 1,4-bis(naphthyl)-1,3-butadiyne of the attachment of terminal alkoxy chains. Liq Cryst. 2003;30:325–329. doi:10.1080/0267829031000071257
   Web of Science ®Google Scholar
• Arakawa Y, Nakajima S, Ishige R, Uchimura M, Kang S. Synthesis of diphenyl-diacetylene-based nematic liquid crystals and their high birefringence properties. J Mater Chem. 2012;22:8394–8398. doi:10.1039/c2jm16002a
   Web of Science ®Google Scholar
• Arakawa Y, Nakajima S, Kang S, Shigeta M, Konishi G. Design of an extremely high birefringence nematic liquid crystal based on a dinaphthyl-diacetylene mesogen. J Mater Chem. 2012;22:13908–13910. doi:10.1039/c2jm32448b
   Web of Science ®Google Scholar
• Arakawa Y, Nakajima S, Kang S, Konishi G, Watanabe J. Synthesis and evaluation of high-birefringence polymethacrylate having a diphenyl-diacetylene LC moiety in the side chain. J Mater Chem. 2012;22:14346–14348. doi:10.1039/c2jm32489j
   Web of Science ®Google Scholar
• Uchimura M, Kang S, Ishige R, Watanabe J, Konishi G. Synthesis of liquid crystal molecules based on bis(biphenyl)diacetylene and their liquid crystallinity. Chem Lett. 2010;39:513–515. doi:10.1246/cl.2010.513
   Web of Science ®Google Scholar
• Miao ZC, Wang D, Zhang YM, Jin ZK, Liu F, Wang F, Yang H. Asymmetrical phenyldiacetylenes liquid crystalline compounds with high birefringence and characteristics of selective reflection. Liq Cryst. 2012;39:1291–1296. doi:10.1080/02678292.2012.714801
   Web of Science ®Google Scholar
• Tietz JI, Mastriana JR, Sampson P, Seed AJ. Novel 5-(4-alkoxyphenyl)thieno[3,2-b]thiophene-2-carboxylate esters: highly efficient synthesis and mesogenic evaluation of a new class of materials exhibiting the smectic C phase. Liq Cryst. 2012;39:515–530. doi:10.1080/02678292.2012.657698
   Web of Science ®Google Scholar
• Friedman MR, Toyne KJ, Goodby JW, Hird M. The synthesis and transition temperatures of 2-(4-alkyl- and 4-alkoxy-phenyl)-5-cyano-1-benzofurans and related diaryl-1-benzofurans—an assessment of how deviations from linearity and conformational effects in a core unit affect mesogenicity. J Mater Chem. 2001;11:2759–2772. doi:10.1039/b102837p
   Web of Science ®Google Scholar
• Kovářová A, Svoboda J, Novotná V, Glogarová M, Salamonczyk M, Pociecha D, Gorecka E. [2]Benzothiophene bent-shaped liquid crystals. Liq Cryst. 2010;37:1501–1513. doi:10.1080/02678292.2010.530299
   Web of Science ®Google Scholar
• Kang S, Nakajima S, Arakawa Y, Konishi G, Watanabe J. Large extraordinary refractive index in highly birefringent nematic liquid crystals of dinaphthyldiacetylene-based materials. J Mater Chem C. 2013;1:4222–4226. doi:10.1039/c3tc30640b
   Web of Science ®Google Scholar
• Chai JD, Head-Gordon M. Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. Phys Chem Chem Phys. 2008;10:6615–6620. doi:10.1039/b810189b
   PubMed Web of Science ®Google Scholar
• Hehre WJ, Ditchfield R, Pople JA. Self—consistent molecular orbital methods. XII. Further extensions of gaussian—type basis sets for use in molecular orbital studies of organic molecules. J Chem Phys. 1972;56:2257–2261. doi:10.1063/1.1677527
   Web of Science ®Google Scholar
• Hariharan PC, Pople JA. The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chim Acta. 1973;28:213–222. doi:10.1007/BF00533485
   Google Scholar
• Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery J Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ. Gaussian 09, Revision A.02. Gaussian: Wallingford CT; 2009.
   Google Scholar
• Eakins GL, Alford JS, Tiegs BJ, Breyfogle BE, Stearman CJ. Tuning HOMO–LUMO levels: trends leading to the design of 9-fluorenone scaffolds with predictable electronic and optoelectronic properties. J Phys Org Chem. 2011;24:1119–1128. doi:10.1002/poc.1864
   Web of Science ®Google Scholar
• Niko Y, Kawauchi S, Otsu S, Tokumaru K, Konishi G. Fluorescence enhancement of pyrene chromophores induced by alkyl groups through σ–π conjugation: systematic synthesis of primary, secondary, and tertiary alkylated pyrenes at the 1, 3, 6, and 8 positions and their photophysical properties. J Org Chem. 2013;78:3196–3207. doi:10.1021/jo400128c
   PubMed Web of Science ®Google Scholar
• Zhang LY, Guan XL, Zhang ZL, Chen XF, Shen ZH, Fan XH, Zhou QF. Preparation and properties of highly birefringent liquid crystalline materials: styrene monomers with acetylenes, naphthyl, and isothiocyanate groups. Liq Cryst. 2010;37:453–462. doi:10.1080/02678291003653641
   Web of Science ®Google Scholar
• Kula P, Aptacy A, Herman J, Wójciak W, Urban S. The synthesis and properties of fluoro-substituted analogues of 4-butyl-4′-[(4-butylphenyl)ethynyl]biphenyls. Liq Cryst. 2013;40:482–491. doi:10.1080/02678292.2012.757813
   Web of Science ®Google Scholar
• Kula P, Herman J, Chojnowska O. Synthesis and properties of terphenyl- and quaterphenyl-based chiral diesters. Liq Cryst. 2013;40:83–90. doi:10.1080/02678292.2012.733033
   Web of Science ®Google Scholar
• Jiang Y, Lu LL, Chen P, Chen XB, Li J, An ZW. Synthesis and properties of allyloxy-based biphenyl liquid crystals with multiple lateral fluoro substituents. Liq Cryst. 2012;39:957–963. doi:10.1080/02678292.2012.688224
   Web of Science ®Google Scholar
• Zhang YM, Wang D, Miao ZC, Jin SK, Yang H. Novel high birefringence bistolane liquid crystals with lateral fluorosubstituent. Liq Cryst. 2012;39:1330–1339. doi:10.1080/02678292.2012.725871
   Web of Science ®Google Scholar
• Arakawa Y, Nakajima S, Kang S, Shigeta M, Konishi G. Synthesis and evaluation of dinaphthylacetylene nematic liquid crystals for high-birefringence materials. Liq Cryst. 2012;39:1063–1069. doi:10.1080/02678292.2012.696730
   Web of Science ®Google Scholar
• Herman J, Dziaduszek J, Dąbrowski R, Kędzierski J, Kowiorski K, Dasari VS, Dhara S, Kula P. Novel high birefringent isothiocyanates based on quaterphenyl and phenylethynyltolane molecular cores. Liq Cryst. 2013;40:1174–1182. doi:10.1080/02678292.2013.808768
   Web of Science ®Google Scholar