Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells
Autor(a) principal: | |
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Data de Publicação: | 2017 |
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/1822/50176 |
Resumo: | The effect of anchoring groups on the optical and electrochemical properties of triphenylamine-thienothiophenes, and on the photovoltaic performance of DSSCs photosensitized with the prepared dyes, was studied using newly synthesized compounds with cyanoacetic acid or rhodanine-3-acetic acid groups. Precursor aldehydes were synthesized through Suzuki cross-coupling, whereas Knoevenagel condensation of these with 2-cyanoacetic acid or rhodanine-3-acetic acid afforded the final push–pull dyes. A comprehensive photophysical study was performed in solution and in the solid state. The femtosecond time-resolved transient absorption spectra for the synthesized dyes were obtained following photoexcitation in solution and for the dyes adsorbed to TiO2 mesoporous films. Information on conformation, electronic structure, and electron distribution was obtained by density functional theory (DFT) and time-dependent DFT calculations. Triphenylamine–thienothiophene functionalized with a cyanoacetic acid anchoring group displayed the highest conversion efficiency (3.68%) as the dye sensitizer in nanocrystalline TiO2 solar cells. Coadsorption studies were performed for this dye with the ruthenium-based N719 dye, and they showed dye power conversion efficiencies enhanced by 20–64%. The best cell performance obtained with the coadsorbed N719 and cyanoacetic dye showed an efficiency of 6.05%. |
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Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cellsThieno[3,2-b]thiopheneDye-Sensitized Solar Cells (DSSCs)synthesisPhotovoltaic PropertiesUV-visibleFluorescenceDensity functional theory (DFT) and time-dependent DFT calculationsTriphenylamineFemtosecond time-resolved transient absorption spectraCiências Naturais::Ciências QuímicasScience & TechnologyThe effect of anchoring groups on the optical and electrochemical properties of triphenylamine-thienothiophenes, and on the photovoltaic performance of DSSCs photosensitized with the prepared dyes, was studied using newly synthesized compounds with cyanoacetic acid or rhodanine-3-acetic acid groups. Precursor aldehydes were synthesized through Suzuki cross-coupling, whereas Knoevenagel condensation of these with 2-cyanoacetic acid or rhodanine-3-acetic acid afforded the final push–pull dyes. A comprehensive photophysical study was performed in solution and in the solid state. The femtosecond time-resolved transient absorption spectra for the synthesized dyes were obtained following photoexcitation in solution and for the dyes adsorbed to TiO2 mesoporous films. Information on conformation, electronic structure, and electron distribution was obtained by density functional theory (DFT) and time-dependent DFT calculations. Triphenylamine–thienothiophene functionalized with a cyanoacetic acid anchoring group displayed the highest conversion efficiency (3.68%) as the dye sensitizer in nanocrystalline TiO2 solar cells. Coadsorption studies were performed for this dye with the ruthenium-based N719 dye, and they showed dye power conversion efficiencies enhanced by 20–64%. The best cell performance obtained with the coadsorbed N719 and cyanoacetic dye showed an efficiency of 6.05%.The authors thank Fundacao para a Ciencia e Tecnologia (FCT) for PhD grants to S.S.M.F. (SFRH/BD/87786/2012) and M.C.R.C. (SFRH/BD/78037/2011) and postdoctoral grants to L.L.G.J. (SFRH/BPD/97026/2013) and J.P. (SFRH/BPD/108469/2015). The authors also thank FEDER-COMPETE for the financial support through the CQ/UM PEst-C/QUI/UI0686/2013 (FCOMP-01-0124-FEDER-037302). The NMR spectrometer Bruker AVANCE III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment, contract REDE/1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT. The group in Coimbra are grateful for funding from "Centro de Quimica de Coimbra," which is supported by the Fundacao para a Ciencia e a Tecnologia (FCT), Portuguese Agency for Scientific Research, through the programs UID/QUI/UI0313/2013 and COMPETE. The authors also thank the Laboratory for Advanced Computing at the University of Coimbra for providing computing resources that have contributed to the research results reported in this paper (URL http://www.lca.uc.pt). This work was performed under the project "SunStorage. harvesting and storage of solar energy,"with reference POCI-01-0145-FEDER-016387, funded by the European Regional Development Fund (ERDF), through COMPETE 2020. Operational Programme for Competitiveness and Internationalization (OPCI), and by national funds through FCT. The research leading to these results has received funding from Laserlab-Europe (grant agreement no. 284464, EC's Seventh Framework Programme). A.I.P. would like to acknowledge the European Commission through the Seventh Framework Programme, the Specific Programme "Ideas" of the European Research Council for research and technological development as part of an Advanced Grant under grant agreement no. 321315, which also partially funded this work. The authors would also like to acknowledge L. Andrade and I. Mesquita for their valuable contribution for the article.info:eu-repo/semantics/publishedVersionAmerican Chemical SocietyUniversidade do MinhoFernandes, Sara Sofia MarquesCastro, M. Cidália R.Pereira, Ana IsabelMendes, AdélioSerpa, CarlosPina, JoãoJustino, Licinia L. G.Burrows, Hugh D.Raposo, M. Manuela M.2017-122017-12-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/50176engFernandes, S. S. M.; Castro, M. C. R.; Pereira, A. I.; Mendes, A.; Serpa, C.; Pina, J.; Justino, L. L. G.; Burrows, H. D.; Raposo, M. M. M.; ACS Omega, 2017, 2 (12), pp 9268–92792470-13432470-134310.1021/acsomega.7b01195http://pubs.acs.org/doi/full/10.1021/acsomega.7b01195info: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:RCAAP2023-07-21T12:53:40Zoai:repositorium.sdum.uminho.pt:1822/50176Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:53:05.408086Repositório 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 |
Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells |
title |
Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells |
spellingShingle |
Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells Fernandes, Sara Sofia Marques Thieno[3,2-b]thiophene Dye-Sensitized Solar Cells (DSSCs) synthesis Photovoltaic Properties UV-visible Fluorescence Density functional theory (DFT) and time-dependent DFT calculations Triphenylamine Femtosecond time-resolved transient absorption spectra Ciências Naturais::Ciências Químicas Science & Technology |
title_short |
Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells |
title_full |
Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells |
title_fullStr |
Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells |
title_full_unstemmed |
Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells |
title_sort |
Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells |
author |
Fernandes, Sara Sofia Marques |
author_facet |
Fernandes, Sara Sofia Marques Castro, M. Cidália R. Pereira, Ana Isabel Mendes, Adélio Serpa, Carlos Pina, João Justino, Licinia L. G. Burrows, Hugh D. Raposo, M. Manuela M. |
author_role |
author |
author2 |
Castro, M. Cidália R. Pereira, Ana Isabel Mendes, Adélio Serpa, Carlos Pina, João Justino, Licinia L. G. Burrows, Hugh D. Raposo, M. Manuela M. |
author2_role |
author author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Fernandes, Sara Sofia Marques Castro, M. Cidália R. Pereira, Ana Isabel Mendes, Adélio Serpa, Carlos Pina, João Justino, Licinia L. G. Burrows, Hugh D. Raposo, M. Manuela M. |
dc.subject.por.fl_str_mv |
Thieno[3,2-b]thiophene Dye-Sensitized Solar Cells (DSSCs) synthesis Photovoltaic Properties UV-visible Fluorescence Density functional theory (DFT) and time-dependent DFT calculations Triphenylamine Femtosecond time-resolved transient absorption spectra Ciências Naturais::Ciências Químicas Science & Technology |
topic |
Thieno[3,2-b]thiophene Dye-Sensitized Solar Cells (DSSCs) synthesis Photovoltaic Properties UV-visible Fluorescence Density functional theory (DFT) and time-dependent DFT calculations Triphenylamine Femtosecond time-resolved transient absorption spectra Ciências Naturais::Ciências Químicas Science & Technology |
description |
The effect of anchoring groups on the optical and electrochemical properties of triphenylamine-thienothiophenes, and on the photovoltaic performance of DSSCs photosensitized with the prepared dyes, was studied using newly synthesized compounds with cyanoacetic acid or rhodanine-3-acetic acid groups. Precursor aldehydes were synthesized through Suzuki cross-coupling, whereas Knoevenagel condensation of these with 2-cyanoacetic acid or rhodanine-3-acetic acid afforded the final push–pull dyes. A comprehensive photophysical study was performed in solution and in the solid state. The femtosecond time-resolved transient absorption spectra for the synthesized dyes were obtained following photoexcitation in solution and for the dyes adsorbed to TiO2 mesoporous films. Information on conformation, electronic structure, and electron distribution was obtained by density functional theory (DFT) and time-dependent DFT calculations. Triphenylamine–thienothiophene functionalized with a cyanoacetic acid anchoring group displayed the highest conversion efficiency (3.68%) as the dye sensitizer in nanocrystalline TiO2 solar cells. Coadsorption studies were performed for this dye with the ruthenium-based N719 dye, and they showed dye power conversion efficiencies enhanced by 20–64%. The best cell performance obtained with the coadsorbed N719 and cyanoacetic dye showed an efficiency of 6.05%. |
publishDate |
2017 |
dc.date.none.fl_str_mv |
2017-12 2017-12-01T00:00:00Z |
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/1822/50176 |
url |
http://hdl.handle.net/1822/50176 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Fernandes, S. S. M.; Castro, M. C. R.; Pereira, A. I.; Mendes, A.; Serpa, C.; Pina, J.; Justino, L. L. G.; Burrows, H. D.; Raposo, M. M. M.; ACS Omega, 2017, 2 (12), pp 9268–9279 2470-1343 2470-1343 10.1021/acsomega.7b01195 http://pubs.acs.org/doi/full/10.1021/acsomega.7b01195 |
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.publisher.none.fl_str_mv |
American Chemical Society |
publisher.none.fl_str_mv |
American Chemical Society |
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 |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
collection |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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