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)

Abstract

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
• Status: Published
• Refereed: Yes
• 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: 2050-7526
• 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

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
141731		Physical organic chemistry - opportunities in synthesis, materials and pharmaceuticals	Graeme Cooke	Engineering and Physical Sciences Research Council (EPSRC)	EP/E036244/1	Chemistry