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Facile synthesis of annulated benzothiadiazole derivatives and their application as medium band gap acceptors in organic photovoltaic devices

Xiantao Hu Orcid Logo, Ram Datt, Qiao He Orcid Logo, Panagiota Kafourou Orcid Logo, Harrison Lee, Andrew J. P. White, Wing Chung Tsoi Orcid Logo, Martin Heeney Orcid Logo

Journal of Materials Chemistry C, Volume: 10, Issue: 24, Pages: 9249 - 9256

Swansea University Authors: Ram Datt, Harrison Lee, Wing Chung Tsoi Orcid Logo

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DOI (Published version): 10.1039/d2tc01433e

Abstract

Two 2,1,3-benzothiadiazole derivatives annulated with 2-(1,3-dithiol-2-ylidene)malonitrile in the 4,5-positions were prepared by nucleophilic substitution reactions of a fluorinated precursor. The resulting derivatives were coupled to an electron rich indacenodithiophene core to afford two new non-f...

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Published in: Journal of Materials Chemistry C
ISSN: 2050-7526 2050-7534
Published: Royal Society of Chemistry (RSC) 2022
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URI: https://cronfa.swan.ac.uk/Record/cronfa60168
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spelling 2022-07-06T12:24:04.2682058 v2 60168 2022-06-08 Facile synthesis of annulated benzothiadiazole derivatives and their application as medium band gap acceptors in organic photovoltaic devices 350d1f64ddd9787a6eda98611dcbb8d2 Ram Datt Ram Datt true false 0ef65494d0dda7f6aea5ead8bb6ce466 Harrison Lee Harrison Lee true false 7e5f541df6635a9a8e1a579ff2de5d56 0000-0003-3836-5139 Wing Chung Tsoi Wing Chung Tsoi true false 2022-06-08 MTLS Two 2,1,3-benzothiadiazole derivatives annulated with 2-(1,3-dithiol-2-ylidene)malonitrile in the 4,5-positions were prepared by nucleophilic substitution reactions of a fluorinated precursor. The resulting derivatives were coupled to an electron rich indacenodithiophene core to afford two new non-fullerene acceptors (NFAs). Both NFAs exhibited identical absorption spectra in solution, but significant differences in the solid state as a result of the end group fluorination. Both materials performed as electron acceptors in solar cell blends with donor polymers. The resulting devices exhibited high open circuit voltages over 1 V under 1 sun illumination, as a result of their high lying LUMO levels. Devices based on the fluorinated acceptor demonstrated reasonable performance under low light conditions, with power conversion efficiencies up to 13.7%. Journal Article Journal of Materials Chemistry C 10 24 9249 9256 Royal Society of Chemistry (RSC) 2050-7526 2050-7534 8 6 2022 2022-06-08 10.1039/d2tc01433e COLLEGE NANME Materials Science and Engineering COLLEGE CODE MTLS Swansea University We would like to thank the Engineering and Physics Science Research Council (EPSRC) (EP/N020863/1, EP/V048686/1 and EP/T028513/1) and the Royal Society and Wolfson Foundation for financial support. 2022-07-06T12:24:04.2682058 2022-06-08T17:24:28.3905951 Faculty of Science and Engineering School of Engineering and Applied Sciences - Materials Science and Engineering Xiantao Hu 0000-0002-3472-3288 1 Ram Datt 2 Qiao He 0000-0002-9383-9387 3 Panagiota Kafourou 0000-0001-7082-6527 4 Harrison Lee 5 Andrew J. P. White 6 Wing Chung Tsoi 0000-0003-3836-5139 7 Martin Heeney 0000-0001-6879-5020 8 60168__24462__acbf3629b6e64a71bac2879843831f78.pdf 60168.pdf 2022-07-06T12:21:20.3053115 Output 2723508 application/pdf Version of Record true This article is licensed under a Creative Commons Attribution 3.0 Unported Licence true eng http://creativecommons.org/licenses/by/3.0/
title Facile synthesis of annulated benzothiadiazole derivatives and their application as medium band gap acceptors in organic photovoltaic devices
spellingShingle Facile synthesis of annulated benzothiadiazole derivatives and their application as medium band gap acceptors in organic photovoltaic devices
Ram Datt
Harrison Lee
Wing Chung Tsoi
title_short Facile synthesis of annulated benzothiadiazole derivatives and their application as medium band gap acceptors in organic photovoltaic devices
title_full Facile synthesis of annulated benzothiadiazole derivatives and their application as medium band gap acceptors in organic photovoltaic devices
title_fullStr Facile synthesis of annulated benzothiadiazole derivatives and their application as medium band gap acceptors in organic photovoltaic devices
title_full_unstemmed Facile synthesis of annulated benzothiadiazole derivatives and their application as medium band gap acceptors in organic photovoltaic devices
title_sort Facile synthesis of annulated benzothiadiazole derivatives and their application as medium band gap acceptors in organic photovoltaic devices
author_id_str_mv 350d1f64ddd9787a6eda98611dcbb8d2
0ef65494d0dda7f6aea5ead8bb6ce466
7e5f541df6635a9a8e1a579ff2de5d56
author_id_fullname_str_mv 350d1f64ddd9787a6eda98611dcbb8d2_***_Ram Datt
0ef65494d0dda7f6aea5ead8bb6ce466_***_Harrison Lee
7e5f541df6635a9a8e1a579ff2de5d56_***_Wing Chung Tsoi
author Ram Datt
Harrison Lee
Wing Chung Tsoi
author2 Xiantao Hu
Ram Datt
Qiao He
Panagiota Kafourou
Harrison Lee
Andrew J. P. White
Wing Chung Tsoi
Martin Heeney
format Journal article
container_title Journal of Materials Chemistry C
container_volume 10
container_issue 24
container_start_page 9249
publishDate 2022
institution Swansea University
issn 2050-7526
2050-7534
doi_str_mv 10.1039/d2tc01433e
publisher Royal Society of Chemistry (RSC)
college_str Faculty of Science and Engineering
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hierarchy_top_id facultyofscienceandengineering
hierarchy_top_title Faculty of Science and Engineering
hierarchy_parent_id facultyofscienceandengineering
hierarchy_parent_title Faculty of Science and Engineering
department_str School of Engineering and Applied Sciences - Materials Science and Engineering{{{_:::_}}}Faculty of Science and Engineering{{{_:::_}}}School of Engineering and Applied Sciences - Materials Science and Engineering
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description Two 2,1,3-benzothiadiazole derivatives annulated with 2-(1,3-dithiol-2-ylidene)malonitrile in the 4,5-positions were prepared by nucleophilic substitution reactions of a fluorinated precursor. The resulting derivatives were coupled to an electron rich indacenodithiophene core to afford two new non-fullerene acceptors (NFAs). Both NFAs exhibited identical absorption spectra in solution, but significant differences in the solid state as a result of the end group fluorination. Both materials performed as electron acceptors in solar cell blends with donor polymers. The resulting devices exhibited high open circuit voltages over 1 V under 1 sun illumination, as a result of their high lying LUMO levels. Devices based on the fluorinated acceptor demonstrated reasonable performance under low light conditions, with power conversion efficiencies up to 13.7%.
published_date 2022-06-08T04:18:03Z
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