New thiophene-based conjugated macrocycles for optoelectronic applications

dos Santos, J. M., Jagadamma, L. K., Cameron, J. , Wiles, A. W. , Wilson, C. , Skabara, P. J. , Samuel, I. D.W. and Cooke, G. (2021) New thiophene-based conjugated macrocycles for optoelectronic applications. Journal of Materials Chemistry C, 9(45), pp. 16257-16271. (doi: 10.1039/D1TC02002A)

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Thiophene-based semiconductors are amongst the most successful materials in organic electronics. In this contribution, we present the synthesis and characterisation of two thiophene-based macrocycles as well as their evaluation in organic-electronic devices. McT-1 is composed of ten thiophene moieties, whereas in McT-2, four additional electron-deficient benzothiadiazole moieties are incorporated to form a donor–acceptor (D–A) π-system. Red-shifted and broadened absorption spectra as well as more positive redox potentials are observed in McT-2, whereas McT-1 displays a sharper absorption band with a higher extinction coefficient. Macrocycle McT-1 shows emission in the yellow region whereas McT-2 displays emission in the red wavelength region. DFT calculations predict the macrocycles to comprise of mainly the E,E isomers with a near-planar structure, which is further supported by the single crystal X-ray structure for McT-1. Their charge transporting properties are determined by fabricating thin-film OFETs. The photovoltaic properties of McT-1 and McT-2 are also investigated by fabricating bulk heterojunction (BHJ) devices and their potential as photodetectors has been evaluated.

Item Type:Articles
Glasgow Author(s) Enlighten ID:Skabara, Professor Peter and Cooke, Professor Graeme and Wilson, Dr Claire and Wiles, Dr Alan and Dos Santos, Mr John Marques and Cameron, Dr Joseph
Authors: dos Santos, J. M., Jagadamma, L. K., Cameron, J., Wiles, A. W., Wilson, C., Skabara, P. J., Samuel, I. D.W., and Cooke, G.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Materials Chemistry C
Publisher:Royal Society of Chemistry
ISSN (Online):2050-7534
Published Online:15 July 2021
Copyright Holders:Copyright © 2021 The Royal Society of Chemistry
First Published:First published in Journal of Materials Chemistry C 9(45): 16257-16271
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
141731Physical organic chemistry - opportunities in synthesis, materials and pharmaceuticalsGraeme CookeEngineering and Physical Sciences Research Council (EPSRC)EP/E036244/1Chemistry