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

Rupert G. D. Taylor, Joseph Cameron, Iain A. Wright, Neil Thomson, Olena Avramchenko, Alexander L. Kanibolotsky, Anto R. Inigo, Tell Tuttle, Peter J. Skabara

Research output: Contribution to journalArticle

9 Citations (Scopus)
95 Downloads (Pure)

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.

Original languageEnglish
Pages (from-to)1148-1154
Number of pages7
JournalBeilstein Journal of Organic Chemistry
Volume11
DOIs
Publication statusPublished - 10 Jul 2015

Keywords

  • non-covalent interactions
  • organic field effect transistor (ofet)
  • organic semiconductors
  • tetrathiafulvalene
  • thiazole

Fingerprint Dive into the research topics of 'Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties'. Together they form a unique fingerprint.

Cite this