New thiophene-based conjugated macrocycles for optoelectronic applications

John Marques dos Santos, Lethy Krishnan Jagadamma, Joseph Cameron, Alan A. Wiles, Claire Wilson, Peter J. Skabara, Ifor D. W. Samuel, Graeme Cooke

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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.
Original languageEnglish
Number of pages15
JournalJournal of Materials Chemistry C
VolumeAdvance Article
Early online date15 Jul 2021
DOIs
Publication statusE-pub ahead of print - 15 Jul 2021

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