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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;4-b ']dithiophene-2;6(4H)-dione;Gibbs free energy calculations;Solvent effects | 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 | Rights: | 2013 Elsevier Ltd. All rights reserved. | Category: | A1 | Type: | Journal Contribution | Validations: | ecoom 2014 |
Appears in Collections: | Research publications |
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