New thiophene-based conjugated macrocycles for optoelectronic applications
| Autor: | Alan A. Wiles, Ifor D. W. Samuel, Claire Wilson, Peter J. Skabara, John Marques dos Santos, Lethy Krishnan Jagadamma, Joseph Cameron, Graeme Cooke |
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| Přispěvatelé: | European Commission, University of St Andrews. School of Chemistry, University of St Andrews. School of Physics and Astronomy, University of St Andrews. Centre for Energy Ethics, University of St Andrews. Centre for Biophotonics, University of St Andrews. Condensed Matter Physics |
| Rok vydání: | 2021 |
| Předmět: |
Materials science
Absorption spectroscopy 02 engineering and technology Conjugated system 010402 general chemistry Photochemistry 01 natural sciences 7. Clean energy Polymer solar cell chemistry.chemical_compound Materials Chemistry Thiophene QD SDG 7 - Affordable and Clean Energy Organic electronics business.industry DAS General Chemistry QD Chemistry 021001 nanoscience & nanotechnology 0104 chemical sciences Semiconductor chemistry Absorption band 0210 nano-technology business Single crystal |
| Zdroj: | Journal of Materials Chemistry C. 9:16257-16271 |
| ISSN: | 2050-7534 2050-7526 |
| Popis: | GC acknowledges the EPSRC for funding (EP/E036244/1). JMS acknowledges the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior – Brasil (CAPES) – Finance Code 001 for PhD funding. JMS also acknowledges Dr Nor Basid Adiwibawa Prasetya for helpful advice. Dr L. K. Jagadamma acknowledges support from a Marie Skłodowska-Curie Individual Fellowship (European Commission) (MCIF: No. 745776). 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. Publisher PDF |
| Databáze: | OpenAIRE |
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