Structures of bromoinated oligothiophenes and ethylenedioxythiophenes: A combined experimental and theoretical study

Mamoun M. Bader, Phuong Truc T. Pham

Research output: Chapter in Book/Report/Conference proceedingConference contribution


In this work, we report the results of solid state structural study of a series of oligothiophenes and ethylenedioxythiophenes (EDOT) endowed with bromine atoms at different positions and in the presence/absence of the strong electron acceptor, the tricyanovinyl group (TCV). Five new compounds were synthesized, crystallized and their single crystal structures were determined by X-ray diffraction. The impact of bromine atom(s) on solid state packing as viewed through analysis of intermolecular interactions is presented. Comparative study using experimental, computed and published data of closely related structures shows intra-molecular interactions involving Br in the presence of TCV and EDOT. Distances shorter that the summation of the Van der Waals radii were observed which indicate the role of Br...NC, S...S and Br...Br interactions in addition to pi stack formation and planarity of these compounds due to the presence of strong electron acceptors. Possible implications of how these structural features may impact charge transport in oligothiophenes will be discussed.

Original languageEnglish (US)
Title of host publicationCharge Generation/Transport in Organic Semiconductor Materials
Number of pages6
StatePublished - 2011
Event2011 MRS Fall Meeting - Boston, MA, United States
Duration: Nov 28 2011Dec 2 2011

Publication series

NameMaterials Research Society Symposium Proceedings
ISSN (Print)0272-9172


Other2011 MRS Fall Meeting
Country/TerritoryUnited States
CityBoston, MA

All Science Journal Classification (ASJC) codes

  • General Materials Science
  • Condensed Matter Physics
  • Mechanics of Materials
  • Mechanical Engineering


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