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

Beilstein Journal of Organic Chemistry

Joseph Cameron¹  Olena Avramchenko¹  Neil Thomson¹  Peter J. Skabara¹  Rupert G. D. Taylor¹  Iain A. Wright¹  Anto R. Inigo¹  Alexander L. Kanibolotsky¹  Tell Tuttle¹ 

[1] WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, United Kingdom;

关键词: non-covalent interactions;    organic field effect transistor (OFET);    organic semiconductors;    tetrathiafulvalene;    thiazole;   

DOI  :  10.3762/bjoc.11.129

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown