Low molar mass thieno[3,2-b] and thieno[2,3-b]thiophenes in liquid crystal materials science: recent synthetic approaches

References

• Kline RJ, DeLongchamp DM, Fischer DA, Lin EK, Heeney M, McCulloch I, Toney MF. Significant dependence of morphology and charge carrier mobility on substrate surface chemistry in high performance polythiophene semiconductor films. Appl Phys Lett. 2007;90:062117–3. doi:10.1063/1.2472533.
   Web of Science ®Google Scholar
• DeLongchamp DM, Kline RJ, Jung Y, Germack DS, Lin EK, Moad AJ, Richter LJ, Toney MF, Heeney M, McCulloch I. Controlling the orientation of terraced nanoscale “ribbons” of a poly(thiophene) semiconductor. ACS Nano. 2009;3:780–787. doi:10.1021/nn800574f.
   PubMed Web of Science ®Google Scholar
• Lee J-Y, Shin W-S, Haw J-R, Moon D-K. Low band-gap polymers based on quinoxaline derivatives and fused thiophene as donor materials for high efficiency bulk-heterojunction photovoltaic cells. J Mater Chem. 2009;19:4938–4945. doi:10.1039/b823536h.
   Web of Science ®Google Scholar
• Biniek L, Chochos CL, Leclerc N, Hadziioannou G, Kallitsis JK, Bechara R, Lévêque P, Heiser T. A [3,2-b]thienothiophene-alt-benzothiadiazole copolymer for photovoltaic applications: design, synthesis, material characterization and device performances. J Mater Chem. 2009;19:4946–4951. doi:10.1039/b819177h.
   Web of Science ®Google Scholar
• Zhang L, Liu F, Diao Y, Marsh HS, Colella NS, Jayaraman A, Russell TP, Mannsfeld SCB, Briseno AL. The good host: formation of discrete one-dimensional fullerene “channels” in well-ordered poly(2,5-bis(3-alkylthiophen-2-yl)thieno[3,2-b]thiophene) oligomers. J Am Chem Soc. 2014;136:18120–18130. doi:10.1021/ja510976n.
   PubMed Web of Science ®Google Scholar
• Lucas LA, DeLongchamp DM, Vogel BM, Lin EK, Fasolka MJ, Fischer DA, McCulloch I, Heeney M, Jabbour GE. Combinatorial screening of the effect of temperature on the microstructure and mobility of a high performance polythiophene semiconductor. Appl Phys Lett. 2007;90:012112–3. doi:10.1063/1.2404934.
   Web of Science ®Google Scholar
• Umeda T, Kumaki D, Tokito S. Surface-energy-dependent field-effect mobilities up to 1 cm2/V s for polymer thin-film transistor. J Appl Phys. 2009;105:024516–5. doi:10.1063/1.3072669.
   Web of Science ®Google Scholar
• Heeney M, Bailey C, Genevicius K, Shkunov M, Sparrowe D, Tierney S, McCulloch I. Stable polythiophene semiconductors incorporating thieno[2,3-b]thiophene. J Am Chem Soc. 2005;127:1078–1079. doi:10.1021/ja043112p.
   PubMed Web of Science ®Google Scholar
• Fu Y, Shen W, Li M. Molecular design and density functional theory investigation of novel low-band-gap benzobisthiadiazole-based systems: from monomer to polymer. Polym Int. 2011;60:211–221. doi:10.1002/pi.2928.
   Web of Science ®Google Scholar
• Mashraqui SH, Ghadigaonkar S, Ashraf M, Ranjini AS, Ghosh S, Das PK. Optically transparent and thermally stable nonlinear optic chromophores featuring a thieno[2,3-b]thiophene donor. Tetrahedron. 2007;63:10011–10017. doi:10.1016/j.tet.2007.07.059.
   Web of Science ®Google Scholar
• Blenkle M, Boldt P, Bräuchle C, Grahn W, Ledoux I, Nerenz H, Stadler S, Wichern J, Zyss J. Chalcogens as electron donors for selected nonlinear optic phores.J Chem Soc, Perkin Trans. 1996;2:1377–1384. doi:10.1039/p29960001377.
   Google Scholar
• Yue R, Chen S, Lu B, Liu C, Xu J. Facile electrosynthesis and thermoelectric performance of electroactive free-standing polythieno[3,2-b]thiophene films. J Solid State Electrochem. 2011;15:539–548. doi:10.1007/s10008-010-1095-8.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• Fuller LS, Iddon B, Smith KA. Thienothiophenes. Part 2. Synthesis, metallation and bromine->lithium exchange reactions of thieno[3,2-b]thiophene and its polybromo derivatives. J Chem Soc, Perkin Trans. 1997;1:3465–3470. doi:10.1039/a701877k.
   Google Scholar
• Prugh JD, Hartman GD, Mallorga PJ, McKeever BM, Michelson SR, Murcko MA, Schwam H, Smith RL, Sondey JM, Springer JP, Sugrue MF. New isomeric classes of topically active ocular hypotensive carbonic anhydrase inhibitors: 5-Substituted thieno[2,3-b]thiophene-2-sulfonamides and 5-substituted thieno [3,2-b]thiophene-2-sulfonamides. J Med Chem. 1991;34:1805–1818. doi:10.1021/jm00110a008.
   PubMed Web of Science ®Google Scholar
• Rutherford DR, Stille JK, Elliott CM, Reichert VR. Poly(2,5-ethynylenethiophenediylethynylenes), related heteroaromatic analogs, and poly(thieno[3,2-b]thiophenes): synthesis and thermal and electrical properties. Macromolecules. 1992;25:2294–2306. doi:10.1021/ma00035a003.
   Web of Science ®Google Scholar
• Prim D, Kirsch G. Synthesis of new 2-arylthieno[3,2-b]thiophenes. J Chem Soc., Perkin Trans. 1994;1:2603–2606. doi:10.1039/p19940002603.
   Google Scholar
• Hassner A, Alexanian V. Direct room temperature esterification of carboxylic acids. Tetrahedron Lett. 1978;19:4475–4478. doi:10.1016/S0040-4039(01)95256-6.
   Google Scholar
• Neises B, Steglich W. 4-dialkylaminopyridines as acylation catalysts. Part 5. Simple method for the esterification of carboxylic acids. Angew Chem, Int Ed. 1978;17:522–524. doi:10.1002/anie.197805221.
   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
• Trofimov BA, Sobenina LN, Mikhaleva AI, Sergeeva MP, Nesterenko RN, Golovanova NI, Polovnikova PI. Addition of methyl mercaptoacetate to N-vinylpyrroles. Chem Heterocycl Comp. 1992;28:403–405. doi:10.1007/BF00766997.
   Google Scholar
• Woulfe SR, Miller MJ. The synthesis of substituted [[3(S)-(acylamino)-2-oxo-1-azetidinyl]thio]acetic acids. J Org Chem. 1986;51:3133–3139. doi:10.1021/jo00366a010.
   Web of Science ®Google Scholar
• Boutevin B, Hervaud Y, Mouledous G, Pelaprat N. Synthesis of thiols bearing phosphonate groups. Phosphorus, Sulfur Silicon Relat Elem. 1998;140:125–133. doi:10.1080/10426509808035738.
   Web of Science ®Google Scholar
• Baker BR, Querry MV, Safir SR, Bernstein S, Biotin I. 2-Alkylthiophane-3,4-dicarboxylic acids. J Org Chem. 1947;12:138–154. doi:10.1021/jo01165a018.
   PubMed Web of Science ®Google Scholar
• Seliger H, Görtz -H-H. Synthesis of aliphatic sulfenyl halides containing ester groups. Synth Commun. 1980;10:175–182. doi:10.1080/00397918008064219.
   Web of Science ®Google Scholar
• Hanif RM, Qineng P, Fenzhu M. Synthesis and effect of two new penetration enhancers on the transdermal delivery of 5-fluorouracil through excised rat skin. Chem Pharm Bull. 1998;46:1428–1431. doi:10.1248/cpb.46.1428.
   PubMed Web of Science ®Google Scholar
• Sánchez-Carrera RS, Odom SA, Kinnibrugh TL, Sajoto T, Kim E-G, Timofeeva TV, Barlow S, Coropceanu V, Marder SR, Brédas J-L. Electronic Properties of the 2,6-Diiododithieno[3,2-b:2′,3′-d]thiophene molecule and crystal: a joint experimental and theoretical study. J Phys Chem B. 2010;114:749–755. doi:10.1021/jp909164w.
   PubMed Web of Science ®Google Scholar
• Wong H-L, Tao C-H, Zhu N, Yam V-W-W. Photochromic alkynes as versatile building blocks for metal alkynyl systems: design, synthesis, and photochromic studies of diarylethene-containing platinum(II) phosphine alkynyl complexes. Inorg Chem. 2011;50:471–481. doi:10.1021/ic101298c.
   PubMed Web of Science ®Google Scholar
• Sato M, Kitamura T, Masiko T, Unoura K. Synthesis and some properties of binuclear ruthenocene derivatives bridged by both ethene and thiophene derivatives. J Organomet Chem. 2008;693:247–256. doi:10.1016/j.jorganchem.2007.07.057.
   Web of Science ®Google Scholar
• Gillis EP, Burke MD. A simple and modular strategy for small molecule synthesis:  iterative Suzuki−Miyaura coupling of B-protected haloboronic acid building blocks. J Am Chem Soc. 2007;129:6716–6717. doi:10.1021/ja0716204.
   PubMed Web of Science ®Google Scholar
• Knapp DM, Gillis EP, Burke MD. A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates. J Am Chem Soc. 2009;131:6961–6963. doi:10.1021/ja901416p.
   PubMed Web of Science ®Google Scholar
• Molander GA, Ellis N. Organotrifluoroborates: protected boronic acids that expand the versatility of the Suzuki coupling reaction. Acc Chem Res. 2007;40:275–286. doi:10.1021/ar050199q.
   PubMed Web of Science ®Google Scholar
• Molander GA, Canturk B. Organotrifluoroborates and monocoordinated palladium complexes as catalysts - A perfect combination for Suzuki-Miyaura coupling, Angew. Chem Int Ed. 2009;48:9240–9261. doi:10.1002/anie.200904306.
   PubMed Web of Science ®Google Scholar
• Hayashi N, Mazaki Y, Kobayashi K. Solid-state photosolvolysis of clathrate crystals including ethanol as a guest component. Tetrahedron Lett. 1994;35:5883–5886. doi:10.1016/S0040-4039(00)78209-8.
   Web of Science ®Google Scholar
• Gunasekaran B, Sureshbabu R, Mohanakrishnan AK, Chakkaravarthi G, Manivannan V. Diethyl 3,4-bis(acetoxymethyl)thieno[2,3-b]thiophene-2,5-dicarboxylate. Acta Crystallogr, Sect E: Struct Rep Online. 2009;65:o2455. doi:10.1107/S1600536809036149.
   Google Scholar
• Umadevi M, Sureshbabu R, Mohanakrishnan AK, Chakkaravarthi G, Manivannan V. Diethyl 3,4-bis(2,5-dimethoxybenzyl)thieno[2,3-b]thiophene-2,5-dicarboxylate. Acta Crystallogr., Sect E: Struct Rep Online. 2009;65:o2790. doi:10.1107/S1600536809042214.
   Google Scholar
• Tietz JI. Thienothiophene-based liquid crystals: synthesis and comparative evaluation of mesophase properties [MS thesis]. Kent (OH): Kent State University, 2012.
   Google Scholar
• Gronowitz S, Persson B. A convenient synthesis of thieno[2,3-b]thiophene. Acta Chem Scand. 1967;21:812–813. doi:10.3891/acta.chem.scand.21-0812.
   Google Scholar
• Hawkins DW, Iddon B, Longthorne DS, Rosyk PJ. Synthesis of thieno-[2,3-b]-, -[3,2-b]- and -[3,4-b]-thiophenes and thieno-[3ʹ,2ʹ:4,5]-, -[2ʹ,3ʹ:4,5]- and -[3ʹ,4ʹ:4,5]-thieno[3,2-d]pyrimidin-7(6H)-ones starting from thiophene. J Chem Soc., Perkin Trans. 1994;1:2735–2743. doi:10.1039/p19940002735.
   Google Scholar
• Comel A, Sommen G, Kirsch G. Thienothiophenes: synthesis and applications. Mini-Rev Org Chem. 2004;1:367–374. doi:10.2174/1570193043403118.
   Web of Science ®Google Scholar
• Kiryanov AA, Sampson P, Seed AJ. Synthesis of 2-alkoxy-substituted thiophenes, 1,3-thiazoles, and related S-Heterocycles via Lawesson’s reagent-mediated cyclization under microwave irradiation: applications for liquid crystal synthesis. J Org Chem. 2001;66:7925–7929. doi:10.1021/jo016063x.
   PubMed Web of Science ®Google Scholar
• Sonpatki VM, Herbert MR, Sandvoss LM, Seed AJ. Troublesome alkoxythiophenes. A highly efficient synthesis via cyclization of γ-keto esters. J Org Chem. 2001;66:7283–7286. doi:10.1021/jo015644j.
   PubMed Web of Science ®Google Scholar
• Kiryanov AA, Sampson P, Seed AJ. 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. 2001;11:3068–3077. doi:10.1039/b102059p.
   Web of Science ®Google Scholar
• Gronowitz S, Hoffman RA. Unsaturated γ-thiolactones I. Structures of 2-thienol and the so-called thiotenol. Ark Kemi. 1960;15:499–512.
   Google Scholar
• Tietz JI, Seed AJ, Sampson P. Preparation of brominated 2-alkoxythiophenes via oxidation and etherification of 2-thienyltrifluoroborate salts. Org Lett. 2012;14:5058–5061. doi:10.1021/ol3022897.
   PubMed Web of Science ®Google Scholar
• Kano S, Yuasa Y, Yokomatsu T, Shibuya S. Synthesis of 2-substituted 3,5-dibromothiophenes through base-catalyzed halogen dance reaction of 2,5-dibromothiophene. Heterocycles. 1983;20:2035–2037. doi:10.3987/R-1983-10-2035.
   Web of Science ®Google Scholar
• Fröhlich J. Halogen dance reactions at thiophenes and furans: selective access to a variety of new trisubstituted derivatives. Bull Soc Chim Belg. 1996;105:615–634.
   Google Scholar
• Molander GA, Cavalcanti LN. Oxidation of organotrifluoroborates via Oxone. J Org Chem. 2011;76:623–630. doi:10.1021/jo102208d.
   PubMed Web of Science ®Google Scholar
• Harris CS, Germain H, Pasquet G. Facile preparation of thiophene C2-ethers using the Mitsunobu reaction. Tetrahedron Lett. 2008;49:5946–5949. doi:10.1016/j.tetlet.2008.07.153.
   Web of Science ®Google Scholar
• Yu Y, Sampson P, Seed AJ. New methodological developments in the synthesis of fluorinated and non-fluorinated liquid crystalline thieno[2,3-b] and [3,2-b]thiophene derivatives [MS thesis]. Kent (OH): Kent State University; 2015.
   Google Scholar
• Pedulli GF, Tiecco M, Alberti A, Martelli G. Radical anions of substituted thienothiophens. J Chem Soc. Perkin Trans 2. 1973;1816–1820. doi:10.1039/p29730001816.
   Google Scholar
• Bugge A. Proton magnetic resonance of thieno[2,3-b]thiophene and thieno[3,2-b]thiophene - α-substituent effects on proton chemical shifts. Chem Scr. 1973;3:190–192.
   Google Scholar
• Catel J-M, Mollier Y. Heterocyclic sulfur compounds. XCVII. Reactivity of 3-(methylthio)-1,2-dithiolylium ions with propenenitrile derivatives in a basic medium. Bull Soc Chim Fr. 1982;343–351.
   Google Scholar
• Kantlehner W, Haubner M, Vettel M, Orthoamides IL. Reactions of orthoamide derivatives with sulfur and selenium, syntheses of 1,3-thiazole- and 1,3-selenazole derivatives. J Prakt Chem/Chem- Ztg. 1996;338:403–413. doi:10.1002/prac.19963380180.
   Web of Science ®Google Scholar
• Gaumont AC, Wazneh L, Denis JM. Thiocyanohydrins, a new class of compounds, precursors of unstabilized thiocarbonyl derivatives. Tetrahedron. 1991;47:4927–4940. doi:10.1016/S0040-4020(01)80958-3.
   Web of Science ®Google Scholar