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

doi:10.3762/bjoc.11.129

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^*

^*Corresponding author for this work

School of Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	1148-1154
Number of pages	7
Journal	Beilstein Journal of Organic Chemistry
Volume	11
DOIs	https://doi.org/10.3762/bjoc.11.129
Publication status	Published - 10 Jul 2015

Keywords / Materials (for Non-textual outputs)

Non-covalent interactions
Organic field effect transistor (ofet)
Organic semiconductors
Tetrathiafulvalene
Thiazole

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10.3762/bjoc.11.129

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Taylor, R. G. D., Cameron, J., Wright, I. A., Thomson, N., Avramchenko, O., Kanibolotsky, A. L., Inigo, A. R., Tuttle, T., & 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, 1148-1154. https://doi.org/10.3762/bjoc.11.129

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title = "Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: The effect of planarisation on charge transport properties",

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.",

keywords = "Non-covalent interactions, Organic field effect transistor (ofet), Organic semiconductors, Tetrathiafulvalene, Thiazole",

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

note = "Publisher Copyright: {\textcopyright} 2015 Taylor et al; licensee Beilstein-Institut.",

year = "2015",

month = jul,

day = "10",

doi = "10.3762/bjoc.11.129",

language = "English",

volume = "11",

pages = "1148--1154",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

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TY - JOUR

T1 - Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene

T2 - The effect of planarisation on charge transport properties

AU - Taylor, Rupert G.D.

AU - Cameron, Joseph

AU - Wright, Iain A.

AU - Thomson, Neil

AU - Avramchenko, Olena

AU - Kanibolotsky, Alexander L.

AU - Inigo, Anto R.

AU - Tuttle, Tell

AU - Skabara, Peter J.

PY - 2015/7/10

Y1 - 2015/7/10

N2 - 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.

AB - 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.

KW - Non-covalent interactions

KW - Organic field effect transistor (ofet)

KW - Organic semiconductors

KW - Tetrathiafulvalene

KW - Thiazole

U2 - 10.3762/bjoc.11.129

DO - 10.3762/bjoc.11.129

M3 - Article

AN - SCOPUS:84938704982

SN - 1860-5397

VL - 11

SP - 1148

EP - 1154

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

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

Abstract

Keywords / Materials (for Non-textual outputs)

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