Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties

Taylor, R. G.D., Cameron, J. , Wright, I. A., Thomson, N., Avramchenko, O., Kanibolotsky, A. L., Inigo, A. R., Tuttle, T. and Skabara, P. J. (2015) Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties. Beilstein Journal of Organic Chemistry, 11, pp. 1148-1154. (doi: 10.3762/bjoc.11.129) (PMID:26199671) (PMCID:PMC4505100)

Abstract

Two novel tetrathiafulvalene (TTF) containing compounds 1 and 2 have been synthesised via a four-fold Stille coupling between a tetrabromo-dithienoTTF 5 and stannylated thiophene 6 or thiazole 4. The optical and electrochemical properties of compounds 1 and 2 have been measured by UV–vis spectroscopy and cyclic voltammetry and the results compared with density functional theory (DFT) calculations to confirm the observed properties. Organic field effect transistor (OFET) devices fabricated from 1 and 2 demonstrated that the substitution of thiophene units for thiazoles was found to increase the observed charge transport, which is attributed to induced planarity through S–N interactions of adjacent thiazole nitrogen atoms and TTF sulfur atoms and better packing in the bulk.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Cameron, Dr Joseph and Skabara, Professor Peter
• Authors: Taylor, R. G.D., Cameron, J., Wright, I. A., Thomson, N., Avramchenko, O., Kanibolotsky, A. L., Inigo, A. R., Tuttle, T., and Skabara, P. J.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Beilstein Journal of Organic Chemistry
• Publisher: Beilstein-Institut
• ISSN: 1860-5397
• ISSN (Online): 1860-5397
• Copyright Holders: Copyright © 2015 Taylor et al.
• First Published: First published in Beilstein Journal of Organic Chemistry 11:1148-1154
• Publisher Policy: Reproduced under a Creative Commons License