Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/14771
Title: Reaction of 4H-cyclopenta[2,1-b:3,4-b ']dthiophenes with NBS-a route toward 2H-cyclopenta[2,1-b:3,4-b ']dithiophene-2,6(4H)-diones
Authors: Marin, Lidia 
Van Mierloo, Sarah 
Zhang, Yuexing
Robeyns, Koen
Champagne, Benoit
Adriaensens, Peter 
Lutsen, Laurence 
Vanderzande, Dirk 
Maes, Wouter 
Issue Date: 2013
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Source: TETRAHEDRON, 69 (10), p. 2260-2267
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. (C) 2013 Elsevier Ltd. All rights reserved.
Notes: [Marin, Lidia; Van Mierloo, Sarah; Adriaensens, Peter; Vanderzande, Dirk; Maes, Wouter] Hasselt Univ, Inst Mat Res IMO IMOMEC, B-3590 Diepenbeek, Belgium. [Zhang, Yuexing; Champagne, Benoit] Univ Namur, Lab Chim Theor, B-5000 Namur, Belgium. [Robeyns, Koen] Catholic Univ Louvain, Inst Condensed Matter & Nanosci Mol Solids & Reac, B-1348 Louvain, Belgium. [Lutsen, Laurence; Vanderzande, Dirk] IMOMEC Ass Lab, IMEC, B-3590 Diepenbeek, Belgium.
Keywords: 4H-Cyclopenta[2,1-b:3,4-b ']dithiophene (CPDT); Bromination; 2H-Cyclopenta[2,1-b:3,4-b ']dithiophene-2,6(4H)-dione; Gibbs free energy calculations; Solvent effects;Chemistry, Organic
Document URI: http://hdl.handle.net/1942/14771
ISSN: 0040-4020
e-ISSN: 1464-5416
DOI: 10.1016/j.tet.2013.01.026
ISI #: 000315321500004
Category: A1
Type: Journal Contribution
Validations: ecoom 2014
Appears in Collections:Research publications

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