Issue 45, 2021

New thiophene-based conjugated macrocycles for optoelectronic applications

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.

Graphical abstract: New thiophene-based conjugated macrocycles for optoelectronic applications

Supplementary files

Article information

Article type
Paper
Submitted
30 apr 2021
Accepted
24 jun 2021
First published
15 jul 2021
This article is Open Access
Creative Commons BY license

J. Mater. Chem. C, 2021,9, 16257-16271

New thiophene-based conjugated macrocycles for optoelectronic applications

J. M. dos Santos, L. K. Jagadamma, J. Cameron, A. A. Wiles, C. Wilson, P. J. Skabara, I. D. W. Samuel and G. Cooke, J. Mater. Chem. C, 2021, 9, 16257 DOI: 10.1039/D1TC02002A

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