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

Résultats de recherche: Contribution à un journal/une revueArticle

Résumé

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.
langue originaleAnglais
Pages (de - à)2260-2267
Nombre de pages8
journalTetrahedron
Volume69
Numéro de publication10
Les DOIs
étatPublié - 11 mars 2013

Empreinte digitale

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

Citer ceci

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. Dans: Tetrahedron. 2013 ; Vol 69, Numéro 10. p. 2260-2267.
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title = "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",
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.",
author = "L. Marin and {Van Mierloo}, S. and Y. Zhang and K. Robeyns and B. Champagne and P. Adriaensens and L. Lutsen and D. Vanderzande and W. Maes",
year = "2013",
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Marin, L, Van Mierloo, S, Zhang, Y, Robeyns, K, Champagne, B, Adriaensens, P, Lutsen, L, Vanderzande, D & Maes, W 2013, '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', Tetrahedron, VOL. 69, Numéro 10, p. 2260-2267. https://doi.org/10.1016/j.tet.2013.01.026

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.

Dans: Tetrahedron, Vol 69, Numéro 10, 11.03.2013, p. 2260-2267.

Résultats de recherche: Contribution à un journal/une revueArticle

TY - JOUR

T1 - 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

AU - Marin, L.

AU - Van Mierloo, S.

AU - Zhang, Y.

AU - Robeyns, K.

AU - Champagne, B.

AU - Adriaensens, P.

AU - Lutsen, L.

AU - Vanderzande, D.

AU - Maes, W.

PY - 2013/3/11

Y1 - 2013/3/11

N2 - 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.

AB - 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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U2 - 10.1016/j.tet.2013.01.026

DO - 10.1016/j.tet.2013.01.026

M3 - Article

AN - SCOPUS:84873414089

VL - 69

SP - 2260

EP - 2267

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 10

ER -