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Twist and Degrade-Impact of Molecular Structure on the Photostability of Nonfullerene Acceptors and Their Photovoltaic Blends

Joel Luke, Emily M. Speller, Andrew Wadsworth, Mark F. Wyatt, Stoichko Dimitrov Orcid Logo, Harrison K. H. Lee, Zhe Li Orcid Logo, Wing C. Tsoi, Iain McCulloch, Diego Bagnis, James Durrant Orcid Logo, Ji-Seon Kim, Wing Chung Tsoi Orcid Logo

Advanced Energy Materials, Start page: 1803755

Swansea University Authors: Stoichko Dimitrov Orcid Logo, Zhe Li Orcid Logo, James Durrant Orcid Logo, Wing Chung Tsoi Orcid Logo

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DOI (Published version): 10.1002/aenm.201803755

Abstract

Nonfullerene acceptors (NFAs) dominate organic photovoltaic (OPV) research due to their promising efficiencies and stabilities. However, there is very little investigation into the molecular processes of degradation, which is critical to guiding design of novel NFAs for long‐lived, commercially viab...

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Published in: Advanced Energy Materials
ISSN: 1614-6832
Published: 2019
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URI: https://cronfa.swan.ac.uk/Record/cronfa49112
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However, there is very little investigation into the molecular processes of degradation, which is critical to guiding design of novel NFAs for long&#x2010;lived, commercially viable OPVs. Here, the important role of molecular structure and conformation in NFA photostability in air is investigated by comparing structurally similar but conformationally different promising NFAs: planar O&#x2010;IDTBR and nonplanar O&#x2010;IDFBR. A three&#x2010;phase degradation process is identified: i) initial photoinduced conformational change (i.e., torsion about the core&#x2013;benzothiadiazole dihedral), induced by noncovalent interactions with environmental molecules, ii) followed by photo&#x2010;oxidation and fragmentation, leading to chromophore bleaching and degradation product formation, and iii) finally complete chromophore bleaching. Initial conformational change is a critical prerequisite for further degradation, providing fundamental understanding of the relative stability of IDTBR and IDFBR, where the already twisted IDFBR is more prone to degradation. When blended with the donor polymer poly(3&#x2010;hexylthiophene), both NFAs exhibit improved photostability while the photostability of the polymer itself is significantly reduced by the more miscible twisted NFA. The findings elucidate the important role of NFA molecular structure in photostability of OPV systems, and provide vital insights into molecular design rules for intrinsically photostable NFAs.</abstract><type>Journal Article</type><journal>Advanced Energy Materials</journal><paginationStart>1803755</paginationStart><publisher/><issnPrint>1614-6832</issnPrint><keywords/><publishedDay>31</publishedDay><publishedMonth>12</publishedMonth><publishedYear>2019</publishedYear><publishedDate>2019-12-31</publishedDate><doi>10.1002/aenm.201803755</doi><url/><notes/><college>COLLEGE NANME</college><department>Engineering</department><CollegeCode>COLLEGE CODE</CollegeCode><DepartmentCode>EEN</DepartmentCode><institution>Swansea University</institution><apcterm/><lastEdited>2019-04-11T11:18:54.7574178</lastEdited><Created>2019-03-05T09:30:29.4278725</Created><path><level id="1">Faculty of Science and Engineering</level><level id="2">School of Engineering and Applied Sciences - Materials Science and Engineering</level></path><authors><author><firstname>Joel</firstname><surname>Luke</surname><order>1</order></author><author><firstname>Emily M.</firstname><surname>Speller</surname><order>2</order></author><author><firstname>Andrew</firstname><surname>Wadsworth</surname><order>3</order></author><author><firstname>Mark F.</firstname><surname>Wyatt</surname><order>4</order></author><author><firstname>Stoichko</firstname><surname>Dimitrov</surname><orcid>0000-0002-1564-7080</orcid><order>5</order></author><author><firstname>Harrison K. 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spelling 2019-04-11T11:18:54.7574178 v2 49112 2019-03-05 Twist and Degrade-Impact of Molecular Structure on the Photostability of Nonfullerene Acceptors and Their Photovoltaic Blends 9fc26ec1b8655cd0d66f7196a924fe14 0000-0002-1564-7080 Stoichko Dimitrov Stoichko Dimitrov true false 56be57cc8dd661dfdbb921608cf93ded 0000-0002-7404-7448 Zhe Li Zhe Li true false f3dd64bc260e5c07adfa916c27dbd58a 0000-0001-8353-7345 James Durrant James Durrant true false 7e5f541df6635a9a8e1a579ff2de5d56 0000-0003-3836-5139 Wing Chung Tsoi Wing Chung Tsoi true false 2019-03-05 EEN Nonfullerene acceptors (NFAs) dominate organic photovoltaic (OPV) research due to their promising efficiencies and stabilities. However, there is very little investigation into the molecular processes of degradation, which is critical to guiding design of novel NFAs for long‐lived, commercially viable OPVs. Here, the important role of molecular structure and conformation in NFA photostability in air is investigated by comparing structurally similar but conformationally different promising NFAs: planar O‐IDTBR and nonplanar O‐IDFBR. A three‐phase degradation process is identified: i) initial photoinduced conformational change (i.e., torsion about the core–benzothiadiazole dihedral), induced by noncovalent interactions with environmental molecules, ii) followed by photo‐oxidation and fragmentation, leading to chromophore bleaching and degradation product formation, and iii) finally complete chromophore bleaching. Initial conformational change is a critical prerequisite for further degradation, providing fundamental understanding of the relative stability of IDTBR and IDFBR, where the already twisted IDFBR is more prone to degradation. When blended with the donor polymer poly(3‐hexylthiophene), both NFAs exhibit improved photostability while the photostability of the polymer itself is significantly reduced by the more miscible twisted NFA. The findings elucidate the important role of NFA molecular structure in photostability of OPV systems, and provide vital insights into molecular design rules for intrinsically photostable NFAs. Journal Article Advanced Energy Materials 1803755 1614-6832 31 12 2019 2019-12-31 10.1002/aenm.201803755 COLLEGE NANME Engineering COLLEGE CODE EEN Swansea University 2019-04-11T11:18:54.7574178 2019-03-05T09:30:29.4278725 Faculty of Science and Engineering School of Engineering and Applied Sciences - Materials Science and Engineering Joel Luke 1 Emily M. Speller 2 Andrew Wadsworth 3 Mark F. Wyatt 4 Stoichko Dimitrov 0000-0002-1564-7080 5 Harrison K. H. Lee 6 Zhe Li 0000-0002-7404-7448 7 Wing C. Tsoi 8 Iain McCulloch 9 Diego Bagnis 10 James Durrant 0000-0001-8353-7345 11 Ji-Seon Kim 12 Wing Chung Tsoi 0000-0003-3836-5139 13 0049112-19032019092634.pdf luke2019.pdf 2019-03-19T09:26:34.2130000 Output 1909440 application/pdf Accepted Manuscript true 2020-02-21T00:00:00.0000000 true eng
title Twist and Degrade-Impact of Molecular Structure on the Photostability of Nonfullerene Acceptors and Their Photovoltaic Blends
spellingShingle Twist and Degrade-Impact of Molecular Structure on the Photostability of Nonfullerene Acceptors and Their Photovoltaic Blends
Stoichko Dimitrov
Zhe Li
James Durrant
Wing Chung Tsoi
title_short Twist and Degrade-Impact of Molecular Structure on the Photostability of Nonfullerene Acceptors and Their Photovoltaic Blends
title_full Twist and Degrade-Impact of Molecular Structure on the Photostability of Nonfullerene Acceptors and Their Photovoltaic Blends
title_fullStr Twist and Degrade-Impact of Molecular Structure on the Photostability of Nonfullerene Acceptors and Their Photovoltaic Blends
title_full_unstemmed Twist and Degrade-Impact of Molecular Structure on the Photostability of Nonfullerene Acceptors and Their Photovoltaic Blends
title_sort Twist and Degrade-Impact of Molecular Structure on the Photostability of Nonfullerene Acceptors and Their Photovoltaic Blends
author_id_str_mv 9fc26ec1b8655cd0d66f7196a924fe14
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author_id_fullname_str_mv 9fc26ec1b8655cd0d66f7196a924fe14_***_Stoichko Dimitrov
56be57cc8dd661dfdbb921608cf93ded_***_Zhe Li
f3dd64bc260e5c07adfa916c27dbd58a_***_James Durrant
7e5f541df6635a9a8e1a579ff2de5d56_***_Wing Chung Tsoi
author Stoichko Dimitrov
Zhe Li
James Durrant
Wing Chung Tsoi
author2 Joel Luke
Emily M. Speller
Andrew Wadsworth
Mark F. Wyatt
Stoichko Dimitrov
Harrison K. H. Lee
Zhe Li
Wing C. Tsoi
Iain McCulloch
Diego Bagnis
James Durrant
Ji-Seon Kim
Wing Chung Tsoi
format Journal article
container_title Advanced Energy Materials
container_start_page 1803755
publishDate 2019
institution Swansea University
issn 1614-6832
doi_str_mv 10.1002/aenm.201803755
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 Nonfullerene acceptors (NFAs) dominate organic photovoltaic (OPV) research due to their promising efficiencies and stabilities. However, there is very little investigation into the molecular processes of degradation, which is critical to guiding design of novel NFAs for long‐lived, commercially viable OPVs. Here, the important role of molecular structure and conformation in NFA photostability in air is investigated by comparing structurally similar but conformationally different promising NFAs: planar O‐IDTBR and nonplanar O‐IDFBR. A three‐phase degradation process is identified: i) initial photoinduced conformational change (i.e., torsion about the core–benzothiadiazole dihedral), induced by noncovalent interactions with environmental molecules, ii) followed by photo‐oxidation and fragmentation, leading to chromophore bleaching and degradation product formation, and iii) finally complete chromophore bleaching. Initial conformational change is a critical prerequisite for further degradation, providing fundamental understanding of the relative stability of IDTBR and IDFBR, where the already twisted IDFBR is more prone to degradation. When blended with the donor polymer poly(3‐hexylthiophene), both NFAs exhibit improved photostability while the photostability of the polymer itself is significantly reduced by the more miscible twisted NFA. The findings elucidate the important role of NFA molecular structure in photostability of OPV systems, and provide vital insights into molecular design rules for intrinsically photostable NFAs.
published_date 2019-12-31T03:54:01Z
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