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

Lisa Preti; Rita Cagnoli; Francesca Parenti; Massimiliano Lanzi; Emanuela Libertini; Diego Pinetti; Luisa Schenetti; Adele Mucci

doi:10.1055/s-0029-1218720

PAPER

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

Lisa Preti^a, Rita Cagnoli^a, Francesca Parenti^a, Massimiliano Lanzi^b, Emanuela Libertini^a, Diego Pinetti^c, Luisa Schenetti^a, 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;

Abstract

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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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References

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