Please use this identifier to cite or link to this item: http://hdl.handle.net/1942/14771
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dc.contributor.authorMARIN, Lidia-
dc.contributor.authorVAN MIERLOO, Sarah-
dc.contributor.authorZhang, Yuexing-
dc.contributor.authorRobeyns, Koen-
dc.contributor.authorChampagne, Benoit-
dc.contributor.authorADRIAENSENS, Peter-
dc.contributor.authorLUTSEN, Laurence-
dc.contributor.authorVANDERZANDE, Dirk-
dc.contributor.authorMAES, Wouter-
dc.date.accessioned2013-03-22T08:47:48Z-
dc.date.available2013-03-22T08:47:48Z-
dc.date.issued2013-
dc.identifier.citationTETRAHEDRON, 69 (10), p. 2260-2267-
dc.identifier.issn0040-4020-
dc.identifier.urihttp://hdl.handle.net/1942/14771-
dc.description.abstractIn 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.-
dc.description.sponsorshipWe gratefully thank BELSPO in the frame of the IAP P6/27 and IAP 7/05 networks and the IWT (Institute for the Promotion of Innovation through Science and Technology in Flanders) for financial support by means of the SBO project 060843 ‘PolySpec’. Y.Z. and B.C. acknowledge the financial support of the Fonds Speciaux de Recherche of the Academie universitaire Louvain, co-funded by the Marie Curie Actions of the European Commission (ADi/DB/ 986.2011). The calculations were performed on the Plateforme Technologique de Calcul Intensif of the University of Namur, for which we acknowledge financial support of the F.R.S.-FRFC (Conventions No. 2.4.617.07.F and 2.5020.11), and of the University of Namur.-
dc.language.isoen-
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD-
dc.rights2013 Elsevier Ltd. All rights reserved.-
dc.subject.other4H-Cyclopenta[2-
dc.subject.other1-b:3-
dc.subject.other4-b ']dithiophene (CPDT)-
dc.subject.otherBromination-
dc.subject.other2H-Cyclopenta[2-
dc.subject.other4-b ']dithiophene-2-
dc.subject.other6(4H)-dione-
dc.subject.otherGibbs free energy calculations-
dc.subject.otherSolvent effects-
dc.titleReaction 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-
dc.typeJournal Contribution-
dc.identifier.epage2267-
dc.identifier.issue10-
dc.identifier.spage2260-
dc.identifier.volume69-
local.format.pages8-
local.bibliographicCitation.jcatA1-
dc.description.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.-
local.publisher.placeTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND-
local.type.refereedRefereed-
local.type.specifiedArticle-
dc.identifier.doi10.1016/j.tet.2013.01.026-
dc.identifier.isi000315321500004-
local.uhasselt.internationalno-
item.accessRightsRestricted Access-
item.validationecoom 2014-
item.fulltextWith Fulltext-
item.fullcitationMARIN, Lidia; VAN MIERLOO, Sarah; Zhang, Yuexing; Robeyns, Koen; Champagne, Benoit; ADRIAENSENS, Peter; LUTSEN, Laurence; VANDERZANDE, Dirk & MAES, Wouter (2013) 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. In: TETRAHEDRON, 69 (10), p. 2260-2267.-
item.contributorMARIN, Lidia-
item.contributorVAN MIERLOO, Sarah-
item.contributorZhang, Yuexing-
item.contributorRobeyns, Koen-
item.contributorChampagne, Benoit-
item.contributorADRIAENSENS, Peter-
item.contributorLUTSEN, Laurence-
item.contributorVANDERZANDE, Dirk-
item.contributorMAES, Wouter-
crisitem.journal.issn0040-4020-
crisitem.journal.eissn1464-5416-
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