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Synthesis 2016; 48(23): 4126-4130
DOI: 10.1055/s-0035-1562531
DOI: 10.1055/s-0035-1562531
paper
A Convenient Synthesis of Dithieno[3,2-b:2′,3′-d]thiophenes from Thiophene
Further Information
Publication History
Received: 07 June 2016
Accepted after revision: 15 July 2016
Publication Date:
24 August 2016 (online)
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Abstract
A new synthetic method for dithieno[3,2-b:2′,3′-d]thiophenes was developed. The approach involves three steps starting from thiophene: tetraiodation of thiophene, selective dialkynylations on the 2,5-positions of the tetraiodothiophene, and finally CuI/TMEDA catalyzed double annulations of 2,5-dialkynyl-3,4-diiodothiophenes by Na2S, to afford dithieno[3,2-b:2′,3′-d]thiophene and its derivatives.
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References
- 1a Handbook of Conducting Polymers . 3rd ed.; Skotheim TA, Reynolds JR. CRC Press; New York: 2007
- 1b Fichou D. Handbook of Oligo- and Polythiophene . Wiley-VCH; Weinheim: 1999
- 2a Katz HE. J. Mater. Chem. 1997; 7: 369
- 2b Garnier F. Pure Appl. Chem. 1996; 68: 1455
- 2c Garnier F, Hajlaoui R, Yassar A, Srivastava P. Science 1994; 265: 1684
- 2d Horowitz G, Fichou D, Peng XZ, Xu ZG, Garnier F. Solid State Commun. 1989; 72: 381
- 3a Boudreault PT, Najari A, Leclerc M. Chem. Mater. 2011; 23: 456
- 3b Dennler G, Scharber MC, Brabec CJ. Adv. Mater. 2009; 21: 1313
- 3c Thompson BC, Fréchet JM. J. Angew. Chem. Int. Ed. 2008; 47: 58
- 3d Günes S, Neugebauer H, Sariciftci NS. Chem. Rev. 2007; 107: 1324
- 4 Xiao K, Liu Y, Qi T, Zhang W, Wang F, Gao J, Qiu W, Ma Y, Cui G, Chen S, Zhan X, Yu G, Qin J, Hu W, Zhu D. J. Am. Chem. Soc. 2005; 127: 13281
- 5 Zhang X, Côté AO, Matzger AJ. J. Am. Chem. Soc. 2005; 127: 10502
- 6 Brédas JL, Calbert JP, da Silva DA, Cornil J. Proc. Natl. Acad. Sci. U.S.A. 2002; 99: 5804 ; (calculation)
- 7a Yang YS, Yasuda T, Kakizoe H, Mieno H, Kino H, Tateyama Y, Adachi C. Chem. Commun. 2013; 49: 6483
- 7b Chen M.-C, Chiang Y.-J, Kim C, Guo Y.-J, Chen S.-Y, Liang Y.-J, Huang Y.-W, Hu T.-S, Lee G.-H, Facchetti A, Marks TJ. Chem. Commun. 2009; 1846
- 7c Li X.-C, Sirringhaus H, Garner F, Holmes AB, Moratti SC, Feeder N, Clegg W, Teat SJ, Friend RH. J. Am. Chem. Soc. 1998; 120: 2206
- 7d Sun Y, Ma Y, Liu Y, Lin Y, Wang Z, Wang Y, Di C, Xiao K, Chen X, Qiu W, Zhang B, Yu G, Hu W, Zhu D. Adv. Funct. Mater. 2006; 16: 426
- 7e Liu Y, Di C.-A, Du C, Liu Y, Lu K, Qiu W, Yu G. Chem. Eur. J. 2010; 16: 2231
- 8a Jung JW, Liu F, Russell TP, Jo WH. Energy Environ. Sci. 2012; 5: 6857
- 8b Li J, Tan H.-S, Chen Z.-K, Goh W.-P, Wong H.-K, Ong K.-H, Liu W, Li CM, Ong BS. Macromolecules 2011; 44: 690
- 9a Jong F, Janssen MJ. J. Org. Chem. 1971; 36: 1645
- 9b Barbarella G, Favaretto L, Sotgiu G, Antolini L, Gigli G, Cingolani R, Bongini A. Chem. Mater. 2001; 13: 4112
- 9c Allared F, Hellberg J, Remonen T. Tetrahedron Lett. 2002; 43: 1553
- 9d Frey J, Bond AD, Holmes AB. Chem. Commun. 2002; 2424
- 9e Frey J, Proemmel S, Armitage MA, Holmes AB. Org. Synth. 2006; 11: 209
- 9f Sotgiu G, Zambianchi M, Barbarella G, Aruffo F, Cipriani F, Ventola A. J. Org. Chem. 2003; 68: 1512
- 9g Miguel LS, Porter III WW, Matzger AJ. Org. Lett. 2007; 9: 1005
- 9h He M, Zhang F. J. Org. Chem. 2007; 72: 442
- 9i Kaida H, Satoh T, Hirano K, Miura M. Chem. Lett. 2015; 44: 1125
- 9j Oechsle P, Paradies J. Org. Lett. 2014; 16: 4086
- 10 Steinkopf W, Schmitt HF, Fiedler H. Justus Liebigs Ann. Chem. 1937; 527: 237
- 11 Neenan TX, Whitesides GM. J. Org. Chem. 1988; 53: 2489
- 12 Kashiki T, Shinamura S, Kohara M, Miyazaki E, Takimiya K, Ikeda M, Kuwabara H. Org. Lett. 2009; 11: 2473
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