New 3‐ethynylaryl coumarin‐based dyes for dssc applications
Autor(a) principal: | |
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Data de Publicação: | 2021 |
Outros Autores: | , , , , , , |
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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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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7160 |
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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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1799138079440633856 |