Optical and photovoltaic properties of thieno[3,2-b]thiophene-based push–pull organic dyes with different anchoring groups for dye-sensitized solar cells

Detalhes bibliográficos
Autor(a) principal: Fernandes, Sara Sofia Marques
Data de Publicação: 2017
Outros Autores: Castro, M. Cidália R., Pereira, Ana Isabel, Mendes, Adélio, Serpa, Carlos, Pina, João, Justino, Licinia L. G., Burrows, Hugh D., Raposo, M. Manuela M.
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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spelling 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
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)
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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