Download PDF
Synthesis 2010(10): 1659-1665  
DOI: 10.1055/s-0029-1218720
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Octithiophenes via One-Pot Oxidative Coupling of 4-(ω-Functionalized Alkylsulfanyl)-2,2′-Bithiophenes

Lisa Pretia, Rita Cagnolia, Francesca Parentia, Massimiliano Lanzib, Emanuela Libertinia, Diego Pinettic, Luisa Schenettia, Adele Mucci*a
a Dipartimento di Chimica, Università di Modena e Reggio Emilia, Via G. Campi 183, 41125 Modena, Italy
b Dipartimento di Chimica Industriale e dei Materiali, Università di Bologna, Viale Risorgimento 4, 40136 Bologna, Italy
c Centro Interdipartimentale Grandi Strumenti, Università di Modena e Reggio Emilia, Via G. Campi 213/A, 41125 Modena, Italy
Fax: +39(59)373543; e-Mail: adele.mucci@unimore.it;
Further Information

Publication History

Received 17 February 2010
Publication Date:
06 April 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

The oxidative coupling reaction of nitrile-, methyl ester- and amino-functionalized 4-(alkylsulfanyl)-2,2′-bitiophenes with FeCl3 afforded symmetrical octithiophenes (OTs). These new OTs have solvatochromic properties similar to those reported for poly(w-functionalized alkylsulfanyl)thiophenes and have a potential use in optoelectronic devices. The carboxy-functionalized (obtained through hydrolysis from nitrile and methyl ester functionalized OTs) and the amino-functionalized OTs are also water-soluble as their respective salts. From this and our previous results, the oxidative coupling with FeCl3 can be proposed as a general method for the synthesis of OTs when the starting materials are 4-(alkylsulfanyl)-, 4-(w-functionalized alkylsulfanyl)-, and 4-alkylsulfanyl-4′-halo-2,2′-bithiophenes.

Key words

oligothiophenes - oxidative coupling - alkylsulfanyl octithiophenes - oligomerization - MS and NMR spectroscopy

    References

  • 1 Yassar A. Demanze F. Fichou D. Opt. Mater.  1999,  12:  379 
    CrossrefGoogle Scholar
  • 2a Friend RH. Gymer RW. Holmes AB. Burroughes JH. Marks RN. Taliani C. Bradley DDC. Dos Santos DA. Brédas JL. Lögdlund M. Nature  1999,  397:  121 
    Google Scholar
  • 2b Mazzeo M. Pisignano D. Favaretto L. Barbarella G. Cingolani R. Gigli G. Synth. Met.  2003,  139:  671 
    Google Scholar
  • 3 Huisman B.-H. Valeton JJP. Nijssen W. Lub J. ten Hoeve W. Adv. Mater.  2003,  15:  2002 
    CrossrefGoogle Scholar
  • 4a Murphy AR. Fréchet JMJ. Chang P. Lee J. Subramanian V. J. Am. Chem. Soc.  2004,  126:  1596 
    Google Scholar
  • 4b Videlot-Ackermann C. Ackermann J. Brisset H. Kawamura K. Yoshimoto N. Raynal P. El Kassmi A. Fages F. J. Am. Chem. Soc.  2005,  127:  16346 
    Google Scholar
  • 5 Mishra A. Ma C.-Q. Baüerle P. Chem. Rev.  2009,  109:  1141 
    CrossrefPubMedGoogle Scholar
  • 6 Tamao K. Sumitani K. Kiso Y. Zembayashi M. Fujioka A. Kodama S. Nakajima I. Minato A. Kumada M. Bull. Chem. Soc. Jpn.  1976,  49:  1958 
    CrossrefGoogle Scholar
  • 7 Suzuki A. Pure Appl. Chem.  1991,  63:  419 
    CrossrefGoogle Scholar
  • 8 Stille JK. Angew. Chem. Int. Ed. Engl.  1986,  25:  508 
    Google Scholar
  • 9 Miyasaka M. Rajca A. Synlett  2004,  177 
    Article in Thieme ConnectGoogle Scholar
  • 10 Mucci A. Parenti F. Schenetti L. Zanardi C. Trends Heterocycl. Chem.  2001,  7:  55 
    Google Scholar
  • 11 Iarossi D. Mucci A. Schenetti L. Sodini V. J. Heterocycl. Chem.  1999,  36:  241 
    CrossrefGoogle Scholar
  • 12a Iarossi D. Mucci A. Schenetti L. Seeber R. Goldoni F. Affronte M. Nava F. Macromolecules  1999,  32:  1390 
    Google Scholar
  • 12b Iarossi D. Mucci A. Parenti F. Schenetti L. Seeber R. Zanardi C. Forni A. Tonelli M. Chem. Eur. J.  2001,  7:  676 
    Google Scholar
  • 13 Mucci A. Parenti F. Cagnoli R. Benassi R. Passalacqua A. Preti L. Schenetti L. Macromolecules  2006,  39:  8293 
    CrossrefGoogle Scholar
  • 14 Preti L. Ph.D. Thesis   University of Modena and Reggio Emilia; Italy: 2008. 
    Google Scholar
  • 15a Cagnoli R. Mucci A. Parenti F. Schenetti L. Borsari M. Lodi A. Ponterini G. Polymer  2006,  47:  775 
    Google Scholar
  • 15b Blanchard P. Jousselme B. Frère P. Roncali J.
    J. Org. Chem.  2002,  67:  3961 
    Google Scholar
  • 16 Demeter D. Blanchard P. Grosu I. Roncali J. Electrochem. Commun.  2007,  9:  1587 
    CrossrefGoogle Scholar
  • 17 Domazetis G. Magee RJ. James BD. Cashion JD.
    J. Inorg. Nucl. Chem.  1981,  43:  1351 
    CrossrefGoogle Scholar
  • 18a Bierer DE. Dener JF. Dubenko LG. Gerber RE. Litvak J. Peterli S. Peterli-Roth P. Truong TV. Mao G. Bauer BE. J. Med. Chem.  1995,  38:  2628 
    Google Scholar
  • 18b Gerber RE. Hasbun C. Dubenko LG. King MF. Bierer DE. Org. Synth. Coll. X  2004,  234-239:  186-196  
    Google Scholar
  • 19 Schenetti L. Mucci A. In New Advances in Analytical Chemistry   Vol. 3:  . Taylor & Francis Inc.; New York: 2002.  p.1-40  
    Google Scholar
  • 20 McCarley TD. McCarley RL. Limbach PA. Anal. Chem.  1998,  70:  4376 
    CrossrefGoogle Scholar
  • 21 Liu Y. Zhou J. Wan X. Chen Y. Tetrahedron  2009,  65:  5209 
    CrossrefGoogle Scholar
  • 22a Kiriy N. Jähne E. Adler H.-J. Schneider M. Kiriy A. Gorodyska G. Minko S. Jehnichen D. Simon P. Fokin AA. Stamm M. Nano Lett.  2003,  3:  707 
    Google Scholar
  • 22b Sandstedt CA. Rieke RD. Eckhardt CJ. Chem. Mater.  1995,  7:  1057 
    Google Scholar
  • 22c Langeveld-Voss BMW. Janssen RAJ. Meijer EW. J. Mol. Struct.  2000,  521:  285 
    Google Scholar
  • 23 G oldoni F. Iarossi D. Mucci A. Schenetti L. Zambianchi M. J. Mater. Chem.  1997,  7:  593 
    CrossrefGoogle Scholar
  • 24a Kiriy N. Kiriy A. Bocharova V. Stamm M. Richter S. Plötner M. Fischer W.-J. Krebs FC. Senkovska I. Adler H.-J. Chem. Mater.  2004,  16:  4757 
    Google Scholar
  • 24b Kiriy N. Bocharova V. Kiriy A. Stamm M. Krebs FC. Adler H.-J. Chem. Mater.  2004,  16:  4765 
    Google Scholar
  • 25 Leclère P. Surin M. Viville P. Lazzaroni R. Kilbinger AFM. Henze O. Feast WJ. Cavallini M. Biscarini F. Schenning APHJ. Meijer EW. Chem. Mater.  2004,  16:  4452 ; and references therein
    CrossrefGoogle Scholar
  • 26 Faid K. Cloutier R. Leclerc M. Macromolecules  1993,  26:  2501 
    CrossrefGoogle Scholar
  • 27 Rasmussen SC. Pickens JC. Hutchinson JE.
    J. Heterocycl. Chem.  1997,  34:  285 
    CrossrefGoogle Scholar