New 3‐ethynylaryl coumarin‐based dyes for dssc applications

Detalhes bibliográficos
Autor(a) principal: Sarrato, João
Data de Publicação: 2021
Outros Autores: Pinto, Ana Lucia, Malta, Gabriela, Röck, Eva H., Pina, João, Lima, João Carlos, Parola, A. Jorge, Branco, Paula Sério
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/132978
Resumo: PTDC/QUI‐QOR/7450/2020 POCI‐01‐0145‐FEDER‐016387 UIDB/50006/2020 UIDP/50006/2020 RECI/BBB‐BQB/0230/2012 RECI/BBB‐BEP/0124/2012 2020.09047.BD PD/BD/135087/2017 PD/BD/145324/2019/ (G.M.) .
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spelling New 3‐ethynylaryl coumarin‐based dyes for dssc applicationsSynthesis, spectroscopic properties, and theoretical calculationsCharge transferCoumarin dyesDye‐sensitized solar cellsEthynylarylThieno [3,2‐b] thiopheneAnalytical ChemistryChemistry (miscellaneous)Molecular MedicinePharmaceutical ScienceDrug DiscoveryPhysical and Theoretical ChemistryOrganic ChemistrySDG 7 - Affordable and Clean EnergyPTDC/QUI‐QOR/7450/2020 POCI‐01‐0145‐FEDER‐016387 UIDB/50006/2020 UIDP/50006/2020 RECI/BBB‐BQB/0230/2012 RECI/BBB‐BEP/0124/2012 2020.09047.BD PD/BD/135087/2017 PD/BD/145324/2019/ (G.M.) .A set of 3‐ethynylaryl coumarin dyes with mono, bithiophenes and the fused variant, thieno [3,2‐b] thiophene, as well as an alkylated benzotriazole unit were prepared and tested for dye‐sensitized solar cells (DSSCs). For comparison purposes, the variation of the substitution pattern at the coumarin unit was analyzed with the natural product 6,7‐dihydroxycoumarin (Esculetin) as well as 5,7‐dihydroxycomarin in the case of the bithiophene dye. Crucial steps for extension of the conjugated system involved Sonogashira reaction yielding highly fluorescent molecules. Spectroscopic characterization showed that the extension of conjugation via the alkynyl bridge resulted in a strong red‐shift of absorption and emission spectra (in solution) of approximately 73–79 nm and 52–89 nm, respectively, relative to 6,7‐dimethoxy‐4‐methylcoumarin (λabs = 341 nm and λem = 410 nm). Theoretical density functional theory (DFT) calculations show that the Lowest Unoccupied Molecular Orbital (LUMO) is mostly centered in the cyanoacrylic anchor unit, corroborating the high intramolecular charge transfer (ICT) character of the electronic transition. Photovoltaic performance evaluation reveals that the thieno [3,2‐b] thiophene unit present in dye 8 leads to the best sensitizer of the set, with a conversion efficiency (η = 2.00%), best VOC (367 mV) and second best Jsc (9.28 mA∙cm−2), surpassed only by dye 9b (Jsc = 10.19 mA∙cm−2). This high photocurrent value can be attributed to increased donor ability of the 5,7‐dimethoxy unit when compared to the 6,7 equivalent (9b).LAQV@REQUIMTEDQ - Departamento de QuímicaRUNSarrato, JoãoPinto, Ana LuciaMalta, GabrielaRöck, Eva H.Pina, JoãoLima, João CarlosParola, A. JorgeBranco, Paula Sério2022-02-15T23:36:11Z2021-05-142021-05-14T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10362/132978eng1420-3049PURE: 36679558https://doi.org/10.3390/molecules26102934info: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:RCAAP2024-03-11T05:11:38Zoai:run.unl.pt:10362/132978Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:47:39.163225Repositório 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 New 3‐ethynylaryl coumarin‐based dyes for dssc applications
Synthesis, spectroscopic properties, and theoretical calculations
title New 3‐ethynylaryl coumarin‐based dyes for dssc applications
spellingShingle New 3‐ethynylaryl coumarin‐based dyes for dssc applications
Sarrato, João
Charge transfer
Coumarin dyes
Dye‐sensitized solar cells
Ethynylaryl
Thieno [3,2‐b] thiophene
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
SDG 7 - Affordable and Clean Energy
title_short New 3‐ethynylaryl coumarin‐based dyes for dssc applications
title_full New 3‐ethynylaryl coumarin‐based dyes for dssc applications
title_fullStr New 3‐ethynylaryl coumarin‐based dyes for dssc applications
title_full_unstemmed New 3‐ethynylaryl coumarin‐based dyes for dssc applications
title_sort New 3‐ethynylaryl coumarin‐based dyes for dssc applications
author Sarrato, João
author_facet Sarrato, João
Pinto, Ana Lucia
Malta, Gabriela
Röck, Eva H.
Pina, João
Lima, João Carlos
Parola, A. Jorge
Branco, Paula Sério
author_role author
author2 Pinto, Ana Lucia
Malta, Gabriela
Röck, Eva H.
Pina, João
Lima, João Carlos
Parola, A. Jorge
Branco, Paula Sério
author2_role author
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 Sarrato, João
Pinto, Ana Lucia
Malta, Gabriela
Röck, Eva H.
Pina, João
Lima, João Carlos
Parola, A. Jorge
Branco, Paula Sério
dc.subject.por.fl_str_mv Charge transfer
Coumarin dyes
Dye‐sensitized solar cells
Ethynylaryl
Thieno [3,2‐b] thiophene
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
SDG 7 - Affordable and Clean Energy
topic Charge transfer
Coumarin dyes
Dye‐sensitized solar cells
Ethynylaryl
Thieno [3,2‐b] thiophene
Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry
SDG 7 - Affordable and Clean Energy
description PTDC/QUI‐QOR/7450/2020 POCI‐01‐0145‐FEDER‐016387 UIDB/50006/2020 UIDP/50006/2020 RECI/BBB‐BQB/0230/2012 RECI/BBB‐BEP/0124/2012 2020.09047.BD PD/BD/135087/2017 PD/BD/145324/2019/ (G.M.) .
publishDate 2021
dc.date.none.fl_str_mv 2021-05-14
2021-05-14T00:00:00Z
2022-02-15T23:36:11Z
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/10362/132978
url http://hdl.handle.net/10362/132978
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1420-3049
PURE: 36679558
https://doi.org/10.3390/molecules26102934
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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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