Journal
JOURNAL OF MATERIALS CHEMISTRY C
Volume 9, Issue 45, Pages 16257-16271Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1tc02002a
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Funding
- EPSRC [EP/E036244/1]
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior - Brasil (CAPES) [001]
- Marie Sklodowska-Curie Individual Fellowship (European Commission) [745776]
- Marie Curie Actions (MSCA) [745776] Funding Source: Marie Curie Actions (MSCA)
- EPSRC [EP/E036244/1] Funding Source: UKRI
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The synthesis and characterization of two thiophene-based macrocycles as well as their evaluation in organic electronic devices were presented in this study. The macrocycles McT-1 and McT-2 exhibited different optical and electrochemical properties, with potential applications in photovoltaic devices and photodetectors.
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) pi-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.
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