Tetrathiafulvalene-oligofluorene star-shaped systems: new semiconductor materials for fluorescent moisture indicators

Scanlan, K., Kanibolotskyy, A. L., Breig, B., Hedley, G. J. and Skabara, P. J. (2019) Tetrathiafulvalene-oligofluorene star-shaped systems: new semiconductor materials for fluorescent moisture indicators. Journal of Materials Chemistry C, 7, pp. 6582-6591. (doi: 10.1039/C9TC00845D)

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Abstract

A series of novel star-shaped oligofluorene-thiophene-tetrathiafulvalene systems have been synthesised, following different synthetic routes. Each system incorporates a tetrathiafulvalene redox-active centre and four oligofluorene arms, providing a two-dimensional character of the conjugated backbone. The oligomers differ in the number of fluorene units present in the arms (1 to 4) and the terminal groups at the end of each arm (H or trimethylsilyl). Half-unit oligofluorene systems possessing a 1,3-dithiole-2-one core (a known precursor to the tetrathiafulvalene centre) have been synthesised in order to compare the thermal, optical and electrochemical properties. These half-unit systems consist of a 1,3-dithiole-2-one core fused to a thiophene unit at the 3- and 4- positions. Two oligofluorene arms consisting of 1 to 4 monomer units per arm are positioned at the 4- and 6- positions of the thiophene unit, affording extended conjugation through the thiophene centre. The half-unit systems are found to be moderate emitters in the solution-state, however, the star-shaped systems bearing the tetrathiafulvalene core exhibit inhibited fluorescence in both the solution and solid states. We have demonstrated that the emission of the tetrathiafulvalene systems can be enhanced through the oxidation of the redox-centre followed by a consecutive reaction of the strongly electrophilic tetrathiafulvalene dication with such nucleophiles as water and hydrazine. The result of these reactions leads to an increase in the photoluminescence of these systems, affording the opportunity for the tetrathiafulvalene materials to be used as photonic materials in moisture indicators.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Scanlan, Katrina and Hedley, Dr Gordon and Skabara, Professor Peter and breig, benjamin and Kanibolotskyy, Mr Oleksandr
Authors: Scanlan, K., Kanibolotskyy, A. L., Breig, B., Hedley, G. J., and Skabara, P. J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Materials Chemistry C
Publisher:Royal Society of Chemistry
ISSN:2050-7526
ISSN (Online):2050-7534
Published Online:18 March 2019
Copyright Holders:Copyright © 2019 The Royal Society of Chemistry
First Published:First published in Journal of Materials Chemistry C 7:6582-6591
Publisher Policy:Reproduced under a Creative Commons License
Data DOI:10.5525/gla.researchdata.746

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
3037760Light-controlled manufacturing of semiconductor structures: a platform for next generation processing of photonic devicesPeter SkabaraEngineering and Physical Sciences Research Council (EPSRC)EP/P02744X/2Chemistry
3013270`Hetero-print: A holistic approach to transfer-printing for heterogeneous integration in manufacturingPeter SkabaraEngineering and Physical Sciences Research Council (EPSRC)EP/R03480X/1ENG - Electronics & Nanoscale Engineering