Synthesis and electropolymerization of hexadecyl functionalized bithiophene and thieno[3,2-b]thiophene end-capped with EDOT and EDTT units

McEntee, G. J., Skabara, P. J. , Vilela, F., Tierney, S., Samuel, I. D. W., Gambino, S., Coles, S. J., Hursthouse, M. B., Harrington, R. W. and Clegg, W. (2010) Synthesis and electropolymerization of hexadecyl functionalized bithiophene and thieno[3,2-b]thiophene end-capped with EDOT and EDTT units. Chemistry of Materials, 22(9), pp. 3000-3008. (doi: 10.1021/cm100514r)

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Abstract

The synthesis of three novel thiophene-based conjugated molecules (1−3) is presented. We report the electronic and redox properties of these compounds along with the corresponding electrochemically prepared polymers. The structures of compounds 1 and 2 have been confirmed by single-crystal X-ray diffraction studies. Noncovalent S···O interactions in 1 act to hold the molecule in a planar conformation and this is in stark contrast to the twisted nature of the 3,4-ethylenedithiothiophene (EDTT) analogue. The degree of planarity within the molecules dictates the effective conjugation length within the materials and also the packing of the molecules in the solid state. CGL-TOF studies give hole mobilities up to 4 × 10−5 cm2 V−1 s−1 for compound 1 and 1.5 × 10−5 cm2 V−1 s−1 for 2.

Item Type:Articles
Additional Information:F.V. and P.J.S. thank the EPSRC for funding (EP/E027431).
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Skabara, Professor Peter
Authors: McEntee, G. J., Skabara, P. J., Vilela, F., Tierney, S., Samuel, I. D. W., Gambino, S., Coles, S. J., Hursthouse, M. B., Harrington, R. W., and Clegg, W.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Chemistry of Materials
Publisher:American Chemical Society
ISSN:0897-4756
ISSN (Online):1520-5002
Published Online:02 April 2010

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