Tetrathiafulvalene-oligofluorene star-shaped systems : new semiconductor materials for fluorescent moisture indicators
Scanlan, Katrina and Kanibolotsky, Alexander L. and Breig, Benjamin and Hedley, Gordon J. (2019) Tetrathiafulvalene-oligofluorene star-shaped systems : new semiconductor materials for fluorescent moisture indicators. Journal of Materials Chemistry. C, 7 (22). pp. 6582-6591. ISSN 2050-7526 (https://doi.org/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 to 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 solution, however, the star-shaped systems bearing the tetrathiafulvalene core exhibit inhibited fluorescence in both solution and the solid state. 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.
ORCID iDs
Scanlan, Katrina ORCID: https://orcid.org/0000-0002-2551-0061, Kanibolotsky, Alexander L. ORCID: https://orcid.org/0000-0003-3991-6297, Breig, Benjamin ORCID: https://orcid.org/0000-0001-6290-2673 and Hedley, Gordon J.; Skabara, Peter J.-
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Item type: Article ID code: 68519 Dates: DateEvent14 June 2019Published18 March 2019Published Online13 March 2019AcceptedSubjects: Science > Chemistry Department: Faculty of Science > Pure and Applied Chemistry
Technology and Innovation Centre > PhotonicsDepositing user: Pure Administrator Date deposited: 19 Jun 2019 10:52 Last modified: 11 Nov 2024 12:20 URI: https://strathprints.strath.ac.uk/id/eprint/68519