Exploring the impact of structural rigidification of amino-substituted bio-inspired flavylium dyes in DSSCs

Detalhes bibliográficos
Autor(a) principal: Pinto, Ana Lúcia
Data de Publicação: 2023
Outros Autores: Máximo, Patrícia, Pina, João, Calogero, Giuseppe, Laia, César A. T., Parola, A. Jorge, Lima, J. Carlos
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/156749
Resumo: Publisher Copyright: © 2023 The Authors
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spelling Exploring the impact of structural rigidification of amino-substituted bio-inspired flavylium dyes in DSSCsBio-inspired dyesDye-sensitized solar cellsFlavylium saltsTitanium dioxideChemical Engineering(all)Process Chemistry and TechnologyPublisher Copyright: © 2023 The AuthorsSharing with anthocyanins the 2-phenyl-1-benzopyrylium structural motif, flavylium derivatives are strongly colored bio-inspired dyes that have been explored in dye-sensitized solar cells (DSSCs). Following on the fact that the most efficient flavylium-based dyes for DSSCs require amine electron-donating groups, a diethylamino group and the corresponding rigidified julolidine group were introduced in the benzopyrylium core. This structural variation was combined with another structural parameter – increased planarization of the flavylium ring system – to yield four flavylium derivatives all with a catechol anchoring group. The several pKa values of the new dyes and the UV–vis absorption data at different pH values and upon adsorption to TiO2 (corroborated by TD-DFT calculations) demonstrate a stronger delocalization of the nitrogen lone pair in the julolidine systems when compared to the diethylamino ones, reflecting the stronger electron-donating ability of the former. However, the julolidine-based dyes resulted in a decrease in all DSSC parameters, with efficiencies of 0.6% vs. 2.3% for the diethylamino devices. Discarding eventual increased self-aggregation processes of the more planar julolidine derivatives through studies with a de-aggregating agent (CDCA), and determining comparable dye loadings for all dyes, the presence of increased back-electron transfer processes for the julolidine-based compounds is advanced to explain their lower efficiencies. Rigidification of the flavylium dyes by bridging the benzopyrylium and the phenyl rings is demonstrated by higher fluorescence quantum yields and by electrochemical data and leads to a slight increase in the efficiency of the respective DSSCs. The results contribute to consolidate the potential of flavylium dyes as sensitizers for DSSCs.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNPinto, Ana LúciaMáximo, PatríciaPina, JoãoCalogero, GiuseppeLaia, César A. T.Parola, A. JorgeLima, J. Carlos2023-08-21T22:18:02Z2023-102023-10-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article12application/pdfhttp://hdl.handle.net/10362/156749eng0143-7208PURE: 68027564https://doi.org/10.1016/j.dyepig.2023.111495info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-03-11T05:39:04Zoai:run.unl.pt:10362/156749Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:56:27.033344Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Exploring the impact of structural rigidification of amino-substituted bio-inspired flavylium dyes in DSSCs
title Exploring the impact of structural rigidification of amino-substituted bio-inspired flavylium dyes in DSSCs
spellingShingle Exploring the impact of structural rigidification of amino-substituted bio-inspired flavylium dyes in DSSCs
Pinto, Ana Lúcia
Bio-inspired dyes
Dye-sensitized solar cells
Flavylium salts
Titanium dioxide
Chemical Engineering(all)
Process Chemistry and Technology
title_short Exploring the impact of structural rigidification of amino-substituted bio-inspired flavylium dyes in DSSCs
title_full Exploring the impact of structural rigidification of amino-substituted bio-inspired flavylium dyes in DSSCs
title_fullStr Exploring the impact of structural rigidification of amino-substituted bio-inspired flavylium dyes in DSSCs
title_full_unstemmed Exploring the impact of structural rigidification of amino-substituted bio-inspired flavylium dyes in DSSCs
title_sort Exploring the impact of structural rigidification of amino-substituted bio-inspired flavylium dyes in DSSCs
author Pinto, Ana Lúcia
author_facet Pinto, Ana Lúcia
Máximo, Patrícia
Pina, João
Calogero, Giuseppe
Laia, César A. T.
Parola, A. Jorge
Lima, J. Carlos
author_role author
author2 Máximo, Patrícia
Pina, João
Calogero, Giuseppe
Laia, César A. T.
Parola, A. Jorge
Lima, J. Carlos
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv LAQV@REQUIMTE
DQ - Departamento de Química
RUN
dc.contributor.author.fl_str_mv Pinto, Ana Lúcia
Máximo, Patrícia
Pina, João
Calogero, Giuseppe
Laia, César A. T.
Parola, A. Jorge
Lima, J. Carlos
dc.subject.por.fl_str_mv Bio-inspired dyes
Dye-sensitized solar cells
Flavylium salts
Titanium dioxide
Chemical Engineering(all)
Process Chemistry and Technology
topic Bio-inspired dyes
Dye-sensitized solar cells
Flavylium salts
Titanium dioxide
Chemical Engineering(all)
Process Chemistry and Technology
description Publisher Copyright: © 2023 The Authors
publishDate 2023
dc.date.none.fl_str_mv 2023-08-21T22:18:02Z
2023-10
2023-10-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10362/156749
url http://hdl.handle.net/10362/156749
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0143-7208
PURE: 68027564
https://doi.org/10.1016/j.dyepig.2023.111495
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 12
application/pdf
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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