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)
|
Text
182172.pdf - Published Version Available under License Creative Commons Attribution. 4MB |
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, Dr 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 |
University Staff: Request a correction | Enlighten Editors: Update this record
Altmetric
Altmetric