TY - GEN
T1 - Structures of bromoinated oligothiophenes and ethylenedioxythiophenes
T2 - 2011 MRS Fall Meeting
AU - Bader, Mamoun M.
AU - Pham, Phuong Truc T.
N1 - Funding Information:
The MRSEC Program of the National Science Foundation under Award Number DMR-0212302 partially supported this work. Funding from the University College at Pennsylvania State University is also acknowledged. The authors also acknowledge B. E. Kucera, W. W. Brennessel and V. G. Young, Jr., and the X-Ray Crystallographic Laboratory, Department of Chemistry at the University of Minnesota. The authors would like also to acknowledge the help of John. P. Maciejewski and Wendy Long for their help with initial synthetic work.
Copyright:
Copyright 2013 Elsevier B.V., All rights reserved.
PY - 2011
Y1 - 2011
N2 - 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.
AB - 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.
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U2 - 10.1557/opl.2012.365
DO - 10.1557/opl.2012.365
M3 - Conference contribution
AN - SCOPUS:84879391114
SN - 9781627482202
T3 - Materials Research Society Symposium Proceedings
SP - 72
EP - 77
BT - Charge Generation/Transport in Organic Semiconductor Materials
Y2 - 28 November 2011 through 2 December 2011
ER -