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Structures of Bromoinated Oligothiophenes and Ethylenedioxythiophenes: A Combined Experimental and Theoretical Study

Published online by Cambridge University Press:  21 February 2012

Mamoun M. Bader  and
Phuong-Truc T. Pham
Mamoun M. Bader
Affiliation:
Department of Chemistry, Pennsylvania State University, Hazleton, Pennsylvania. U.S.A. [email protected]
Phuong-Truc T. Pham
Affiliation:
Department of Chemistry, Pennsylvania State University, Worthington Scranton, Pennsylvania, U.S.A.
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Abstract

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.

Keywords

crystallographic structureorganicsemiconducting
Type
Research Article
Information
MRS Online Proceedings Library (OPL) , Volume 1402: Symposium U – Charge Generation/Transport in Organic Semiconductor Materials , 2012 , mrsf11-1402-u08-32
Copyright
Copyright © Materials Research Society 2012

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References

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