Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers 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/1822/48399 |
Resumo: | Five push-pull heterocyclic dyes 4-7, and 9 were synthesized and characterized in order to study the variations in the optical, electronic and photovoltaic properties induced by structural modifications, i.e. different spacer units and anchoring groups. The final push-pull conjugated dyes 6-7 and 9 are formed by a N,N-dimethylaniline donor moiety conjugated with bithiophene, ethynyl-bithiophene or ethynyl-thieno[3,2-b]thiophene spacers and cyanoacetic acid or rhodanine-3-acetic acid as anchoring group. The synthesis of the precursor aldehydes 4-5 was accomplished through a Sonogashira coupling, on the other hand, compound 8 was prepared by Suzuki coupling. Knoevenagel condensation of aldehydes 4, 5 and 8 with cyanoacetic acid or rhodamine-3-acetic acid afforded the final push-pull dyes 6, 7 and 9. Information on conformation, electronic structure and electron distribution was obtained by DFT and TDDFTcalculations. This multidisciplinary study regarding the evaluation of the optical, redox and photovoltaic properties of the dyes reveals that compound 7, bearing an ethynyl-bithiophene spacer conjugated with a cyanoacetic acid anchoring group, has the highest conversion efficiency (3.51 %) as dye sensitizer in nanocrystalline TiO2 solar cells. Co-adsorption studies were also performed for dyes 6-7 with N719 as co-adsorbent, and this enhanced dye efficiencies by 33-45 %. The best cell performance was obtained by co-adsorbing N719 and dye 7 (75/25 vol%) with 4.66 % efficiency. |
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Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cellsDye sensitized solar cellsMetal-free organic dyesBithiopheneThieno[3,2-b]thiopheneCyanoacetic acidRhodanine-3-acetic acidCo-adsorptionCiências Naturais::Ciências QuímicasScience & TechnologyFive push-pull heterocyclic dyes 4-7, and 9 were synthesized and characterized in order to study the variations in the optical, electronic and photovoltaic properties induced by structural modifications, i.e. different spacer units and anchoring groups. The final push-pull conjugated dyes 6-7 and 9 are formed by a N,N-dimethylaniline donor moiety conjugated with bithiophene, ethynyl-bithiophene or ethynyl-thieno[3,2-b]thiophene spacers and cyanoacetic acid or rhodanine-3-acetic acid as anchoring group. The synthesis of the precursor aldehydes 4-5 was accomplished through a Sonogashira coupling, on the other hand, compound 8 was prepared by Suzuki coupling. Knoevenagel condensation of aldehydes 4, 5 and 8 with cyanoacetic acid or rhodamine-3-acetic acid afforded the final push-pull dyes 6, 7 and 9. Information on conformation, electronic structure and electron distribution was obtained by DFT and TDDFTcalculations. This multidisciplinary study regarding the evaluation of the optical, redox and photovoltaic properties of the dyes reveals that compound 7, bearing an ethynyl-bithiophene spacer conjugated with a cyanoacetic acid anchoring group, has the highest conversion efficiency (3.51 %) as dye sensitizer in nanocrystalline TiO2 solar cells. Co-adsorption studies were also performed for dyes 6-7 with N719 as co-adsorbent, and this enhanced dye efficiencies by 33-45 %. The best cell performance was obtained by co-adsorbing N719 and dye 7 (75/25 vol%) with 4.66 % efficiency.Laboratory for Advanced Computing at the University of CoimbraThanks are due to: Fundaçao para a Ci ~ encia e a Tecnologia for ^ PhD grants to S. S. M. Fernandes (SFRH/BD/87786/2012), and I. Mesquita (PD/BD/105985/2014) and a postdoctoral grant to L.L.G.Justino. (SFRH/BPD/97026/2013); FEDER-COMPETE for financial support through the CQ/UM PEst-C/QUI/UI0686/2013 (FCOMP- 01-0124-FEDER-037302); European Research Council (Contract no: 321315) for funding. H. D. Burrows are grateful for funding from Centro de Química de Coimbra, which is supported by the FC through the programmes UID/QUI/UI0313/2013 and COMPETE. 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 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). The authors would like also to acknowledge A. I. Pereira for sequential co-adsorption devices and Dr. D. Ivanou for IPCE experiments.info:eu-repo/semantics/publishedVersionElsevierUniversidade do MinhoFernandes, Sara Sofia MarquesMesquita, I.Andrade, L.Mendes, A.Justino, Licinia L. G.Burrows, H. D.Raposo, M. Manuela M.20172017-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/48399engFernandes, S. S. M.; Mesquita, I.; Andrade, L.; Mendes, A.; Justino, L. L. G. Burrows, H. D.; Raposo, M. M. M. Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells. Org. Electronics 2017, 49, 194-205.1566-11991878-553010.1016/j.orgel.2017.06.048http://dx.doi.org/10.1016/j.orgel.2017.06.048info: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:RCAAP2023-07-21T12:09:17Zoai:repositorium.sdum.uminho.pt:1822/48399Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:00:39.159152Repositório 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 |
Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
title |
Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
spellingShingle |
Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells Fernandes, Sara Sofia Marques Dye sensitized solar cells Metal-free organic dyes Bithiophene Thieno[3,2-b]thiophene Cyanoacetic acid Rhodanine-3-acetic acid Co-adsorption Ciências Naturais::Ciências Químicas Science & Technology |
title_short |
Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
title_full |
Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
title_fullStr |
Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
title_full_unstemmed |
Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
title_sort |
Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells |
author |
Fernandes, Sara Sofia Marques |
author_facet |
Fernandes, Sara Sofia Marques Mesquita, I. Andrade, L. Mendes, A. Justino, Licinia L. G. Burrows, H. D. Raposo, M. Manuela M. |
author_role |
author |
author2 |
Mesquita, I. Andrade, L. Mendes, A. Justino, Licinia L. G. Burrows, H. D. Raposo, M. Manuela M. |
author2_role |
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 Mesquita, I. Andrade, L. Mendes, A. Justino, Licinia L. G. Burrows, H. D. Raposo, M. Manuela M. |
dc.subject.por.fl_str_mv |
Dye sensitized solar cells Metal-free organic dyes Bithiophene Thieno[3,2-b]thiophene Cyanoacetic acid Rhodanine-3-acetic acid Co-adsorption Ciências Naturais::Ciências Químicas Science & Technology |
topic |
Dye sensitized solar cells Metal-free organic dyes Bithiophene Thieno[3,2-b]thiophene Cyanoacetic acid Rhodanine-3-acetic acid Co-adsorption Ciências Naturais::Ciências Químicas Science & Technology |
description |
Five push-pull heterocyclic dyes 4-7, and 9 were synthesized and characterized in order to study the variations in the optical, electronic and photovoltaic properties induced by structural modifications, i.e. different spacer units and anchoring groups. The final push-pull conjugated dyes 6-7 and 9 are formed by a N,N-dimethylaniline donor moiety conjugated with bithiophene, ethynyl-bithiophene or ethynyl-thieno[3,2-b]thiophene spacers and cyanoacetic acid or rhodanine-3-acetic acid as anchoring group. The synthesis of the precursor aldehydes 4-5 was accomplished through a Sonogashira coupling, on the other hand, compound 8 was prepared by Suzuki coupling. Knoevenagel condensation of aldehydes 4, 5 and 8 with cyanoacetic acid or rhodamine-3-acetic acid afforded the final push-pull dyes 6, 7 and 9. Information on conformation, electronic structure and electron distribution was obtained by DFT and TDDFTcalculations. This multidisciplinary study regarding the evaluation of the optical, redox and photovoltaic properties of the dyes reveals that compound 7, bearing an ethynyl-bithiophene spacer conjugated with a cyanoacetic acid anchoring group, has the highest conversion efficiency (3.51 %) as dye sensitizer in nanocrystalline TiO2 solar cells. Co-adsorption studies were also performed for dyes 6-7 with N719 as co-adsorbent, and this enhanced dye efficiencies by 33-45 %. The best cell performance was obtained by co-adsorbing N719 and dye 7 (75/25 vol%) with 4.66 % efficiency. |
publishDate |
2017 |
dc.date.none.fl_str_mv |
2017 2017-01-01T00:00:00Z |
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/1822/48399 |
url |
http://hdl.handle.net/1822/48399 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Fernandes, S. S. M.; Mesquita, I.; Andrade, L.; Mendes, A.; Justino, L. L. G. Burrows, H. D.; Raposo, M. M. M. Synthesis and characterization of push-pull bithiophene and thieno[3,2-b]thiophene derivatives bearing an ethyne linker as sensitizers for dye-sensitized solar cells. Org. Electronics 2017, 49, 194-205. 1566-1199 1878-5530 10.1016/j.orgel.2017.06.048 http://dx.doi.org/10.1016/j.orgel.2017.06.048 |
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 |
Elsevier |
publisher.none.fl_str_mv |
Elsevier |
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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) |
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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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