Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes with NBS - A route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones

L. Marin, S. Van Mierloo, Y. Zhang, K. Robeyns, B. Champagne, P. Adriaensens, L. Lutsen, D. Vanderzande, W. Maes

Research output: Contribution to journalArticle

Abstract

In this paper we present a detailed study of the bromination reaction of cyclopentadithiophene (CPDT) derivatives, by means of NBS, giving access to either 2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophenes or 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones (CPDT-2,6-diones). The CPDT-2,6-diones are fully characterized, including an X-ray single crystal structure of one of the representative materials. A mechanism leading to the formation of the latter, which arise as a new class of compounds within the CPDT family, is proposed and is supported by Gibbs free energy calculations. The influence of the solvent, reaction time, and the number of equivalents of NBS on the selectivity of the reaction is discussed.
Original languageEnglish
Pages (from-to)2260-2267
Number of pages8
JournalTetrahedron
Volume69
Issue number10
DOIs
Publication statusPublished - 11 Mar 2013

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Halogenation
Gibbs free energy
Crystal structure
X-Rays
Single crystals
Derivatives
X rays

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Marin, L. ; Van Mierloo, S. ; Zhang, Y. ; Robeyns, K. ; Champagne, B. ; Adriaensens, P. ; Lutsen, L. ; Vanderzande, D. ; Maes, W. / Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes with NBS - A route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones. In: Tetrahedron. 2013 ; Vol. 69, No. 10. pp. 2260-2267.
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abstract = "In this paper we present a detailed study of the bromination reaction of cyclopentadithiophene (CPDT) derivatives, by means of NBS, giving access to either 2,6-dibromo-4H-cyclopenta[2,1-b:3,4-b′]dithiophenes or 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones (CPDT-2,6-diones). The CPDT-2,6-diones are fully characterized, including an X-ray single crystal structure of one of the representative materials. A mechanism leading to the formation of the latter, which arise as a new class of compounds within the CPDT family, is proposed and is supported by Gibbs free energy calculations. The influence of the solvent, reaction time, and the number of equivalents of NBS on the selectivity of the reaction is discussed.",
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Reaction of 4H-cyclopenta[2,1-b:3,4-b′]dithiophenes with NBS - A route toward 2H-cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-diones. / Marin, L.; Van Mierloo, S.; Zhang, Y.; Robeyns, K.; Champagne, B.; Adriaensens, P.; Lutsen, L.; Vanderzande, D.; Maes, W.

In: Tetrahedron, Vol. 69, No. 10, 11.03.2013, p. 2260-2267.

Research output: Contribution to journalArticle

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AU - Robeyns, K.

AU - Champagne, B.

AU - Adriaensens, P.

AU - Lutsen, L.

AU - Vanderzande, D.

AU - Maes, W.

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