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Volumn 11, Issue 14, 2009, Pages 3144-3147

Facile and scalable synthesis of the fused-ring heterocycles thieno[3,2-b]thiophene and thieno[3,2-b]furan

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Indexed keywords


EID: 67650330047     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9010745     Document Type: Article
Times cited : (63)

References (52)
  • 1
    • 53549105554 scopus 로고    scopus 로고
    • Selected examples include:(a) Fong, H. H.; Pozdin, V. A.; Amassian, A.; Malliaras, G. G.; Smilgies, D. M.; He, M. Q.; Gasper, S.; Zhang, F.; Sorensen, M. J. Am. Chem. Soc. 2008, 130, 13202-13203.
    • Selected examples include:(a) Fong, H. H.; Pozdin, V. A.; Amassian, A.; Malliaras, G. G.; Smilgies, D. M.; He, M. Q.; Gasper, S.; Zhang, F.; Sorensen, M. J. Am. Chem. Soc. 2008, 130, 13202-13203.
  • 18
    • 65149097745 scopus 로고    scopus 로고
    • Selected examples include: (a) McCulloch, I.; Heeney, M.; Chabinyc, M. L.; DeLongchamp, D.; Kline, R. J.; Coelle, M.; Duffy, W.; Fischer, D.; Cundloch, D.; Hamadani, B.; Hamilton, R.; Richter, L.; Salleo, A.; Shkunov, M.; Sporrowe, D.; Tierney, S.; Zhong, W. Adv. Mater. 2009, 21, 1091-1109.
    • Selected examples include: (a) McCulloch, I.; Heeney, M.; Chabinyc, M. L.; DeLongchamp, D.; Kline, R. J.; Coelle, M.; Duffy, W.; Fischer, D.; Cundloch, D.; Hamadani, B.; Hamilton, R.; Richter, L.; Salleo, A.; Shkunov, M.; Sporrowe, D.; Tierney, S.; Zhong, W. Adv. Mater. 2009, 21, 1091-1109.
  • 20
    • 41049098518 scopus 로고    scopus 로고
    • Parmer, J. E.; Mayer, A. C.; Hardin, B. E.; Scully, S. R.; McGehee, M. D.; Heeney, M.; McCulloch, I. Appl. Phys. Lett. 2008, 92, 1133090-1133093.
    • (c) Parmer, J. E.; Mayer, A. C.; Hardin, B. E.; Scully, S. R.; McGehee, M. D.; Heeney, M.; McCulloch, I. Appl. Phys. Lett. 2008, 92, 1133090-1133093.
  • 33
    • 67650304609 scopus 로고    scopus 로고
    • Perhaps even more surprisingly, furano[3,2-fe]furan is unknown
    • Perhaps even more surprisingly, furano[3,2-fe]furan is unknown.
  • 40
    • 67650282959 scopus 로고    scopus 로고
    • Paulmier, C.; Morel, J.; D., S.; Pastour, P. Bull. Soc. Chim. Fr. 1973, 243, 4-2441.
    • Paulmier, C.; Morel, J.; D., S.; Pastour, P. Bull. Soc. Chim. Fr. 1973, 243, 4-2441.
  • 42
    • 67650332342 scopus 로고
    • This method utilizes thiophene-3-thiol, which is not commercially available
    • Ghaisas, V. V.; Tilak, B. D. Proc. Ind. Acad. Sci. 1954, 39A, 14-19. This method utilizes thiophene-3-thiol, which is not commercially available.
    • (1954) Proc. Ind. Acad. Sci , vol.39 A , pp. 14-19
    • Ghaisas, V.V.1    Tilak, B.D.2
  • 43
    • 67650329291 scopus 로고    scopus 로고
    • Although l,2-bis(2,2-diethoxyethyl)disulfide is commercially available, we have adapted a literature procedure to generate the disulfide Supporting Information, Parham, W. E, Wynberg, H. Org. Syn. 1955, 35, 51-52
    • Although l,2-bis(2,2-diethoxyethyl)disulfide is commercially available, we have adapted a literature procedure to generate the disulfide (Supporting Information): Parham, W. E.; Wynberg, H. Org. Syn. 1955, 35, 51-52.
  • 44
    • 67650307734 scopus 로고    scopus 로고
    • The general method used to generate 2 can also be used to make other derivatives and we demonstrate this utility with the production of 3-bromothieno[3,2-fe]thiophene in fewer steps and higher yield than the best literature procedure (Supporting Information).
    • The general method used to generate 2 can also be used to make other derivatives and we demonstrate this utility with the production of 3-bromothieno[3,2-fe]thiophene in fewer steps and higher yield than the best literature procedure (Supporting Information).
  • 45
    • 13644256855 scopus 로고    scopus 로고
    • Slight modifications to the conditions used to obtain 4 were empolyed to generate an isomer, thieno[2,3-b]furan, which has not been previously reported (Supporting Information). Thieno[2,3-b]furan is an analog of cross conjugated thieno[2,3-fe]thiophene, which has been utilized in band gap controlled conjugated copolymers that display among the highest charge carrier mobilities to date for polymer organic thin film transistors: Heeney, M.; Bailey, C.; Genevicius, K.; Shkunov, M.; Sparrowe, D.; Tierney, S.; McCulloch, I. J. Am. Chem. Soc. 2005, 127, 1078-1079.
    • Slight modifications to the conditions used to obtain 4 were empolyed to generate an isomer, thieno[2,3-b]furan, which has not been previously reported (Supporting Information). Thieno[2,3-b]furan is an analog of cross conjugated thieno[2,3-fe]thiophene, which has been utilized in band gap controlled conjugated copolymers that display among the highest charge carrier mobilities to date for polymer organic thin film transistors: Heeney, M.; Bailey, C.; Genevicius, K.; Shkunov, M.; Sparrowe, D.; Tierney, S.; McCulloch, I. J. Am. Chem. Soc. 2005, 127, 1078-1079.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.