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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;
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Publikationsverlauf

Received 17 February 2010
Publikationsdatum:
06. April 2010 (online)

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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

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