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

Lidia Marin, Sarah Van Mierloo, Yuexing Zhang, Koen Robeyns, Benoît Champagne, Peter Adriaensens, Laurence Lutsen, Dirk Vanderzande, Wouter Maes*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


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 (US)
Pages (from-to)2260-2267
Number of pages8
Issue number10
StatePublished - Mar 11 2013
Externally publishedYes


  • 2H-Cyclopenta[2,1-b:3,4-b′]dithiophene-2,6(4H)-dione
  • 4H-Cyclopenta[2,1-b:3,4-b′]dithiophene (CPDT)
  • Bromination
  • Gibbs free energy calculations
  • Solvent effects

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry


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