Synthesis and characterization of aryl-substituted BODIPY dyes displaying distinct solvatochromic singlet oxygen photosensitization efficiencies

Detalhes bibliográficos
Autor(a) principal: Gonçalves, Raquel C. R.
Data de Publicação: 2021
Outros Autores: Pina, João, Costa, Susana P. G., Raposo, M. Manuela M.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: https://hdl.handle.net/1822/78775
Resumo: Three BODIPY derivatives substituted at meso position by aryl (phenyl or N,N-dimethylaminonaphthyl) groups and functionalized at position 2 with electron-withdrawing formyl or electron deficient benzimidazole heterocycle were synthesized and completely characterized by the usual spectroscopic techniques. A comprehensive photophysical study showed a remarkable enhancement of the singlet oxygen sensitization quantum yield for meso-substituted dimethylaminonaphthyl BODIPY with the decrease of the dielectric constant of the solvent (0.02–0.04 for dimethylsulfoxide vs. 0.84 in toluene). In toluene the triplet state formation for the aminonaphthyl substituted BODIPY's was found to be mediated by the intramolecular charge transfer state (ICT), whereas in polar solvents triplet state formation is hindered by fast recombination of the ICT state. Pump-probe transient absorption spectroscopy was used to characterize the photoinduced dynamics of the BODIPY derivatives from the femtosecond to the nanosecond time scale.
id RCAP_32ac36752c982cd9ac26ed27e4cde59b
oai_identifier_str oai:repositorium.sdum.uminho.pt:1822/78775
network_acronym_str RCAP
network_name_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository_id_str 7160
spelling Synthesis and characterization of aryl-substituted BODIPY dyes displaying distinct solvatochromic singlet oxygen photosensitization efficienciesBODIPYIntramolecular charge transferPhotosensitizersSinglet oxygenScience & TechnologyThree BODIPY derivatives substituted at meso position by aryl (phenyl or N,N-dimethylaminonaphthyl) groups and functionalized at position 2 with electron-withdrawing formyl or electron deficient benzimidazole heterocycle were synthesized and completely characterized by the usual spectroscopic techniques. A comprehensive photophysical study showed a remarkable enhancement of the singlet oxygen sensitization quantum yield for meso-substituted dimethylaminonaphthyl BODIPY with the decrease of the dielectric constant of the solvent (0.02–0.04 for dimethylsulfoxide vs. 0.84 in toluene). In toluene the triplet state formation for the aminonaphthyl substituted BODIPY's was found to be mediated by the intramolecular charge transfer state (ICT), whereas in polar solvents triplet state formation is hindered by fast recombination of the ICT state. Pump-probe transient absorption spectroscopy was used to characterize the photoinduced dynamics of the BODIPY derivatives from the femtosecond to the nanosecond time scale.FCT - Laserlab-Europe(REDE/1517/RMN/2005)This work was supported by the Fundação para a Ciˆencia e a Tec nologia (FCT), Portuguese Agency for Scientific Research, through the Coimbra Chemistry Centre projects UIDB/00313/2020 and UIDP/ 00313/2020 and through the Centro de Química (CQUM), project UID/ QUI/00686/2020. 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 Reequipment, contract REDE/ 1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT. Raquel C. R. Gonçalves acknowledges FCT for funding (SFRH/BD/ 05278/2020). The research leading to these results has received funding from Laserlab-Europe (grant agreement no. 284464, EC’s Seventh Framework Programme).ElsevierUniversidade do MinhoGonçalves, Raquel C. R.Pina, JoãoCosta, Susana P. G.Raposo, M. Manuela M.2021-122021-12-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/78775eng0143-720810.1016/j.dyepig.2021.109784https://www.sciencedirect.com/science/article/pii/S0143720821006501?via%3Dihubinfo: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:RCAAP2023-07-21T12:00:05Zoai:repositorium.sdum.uminho.pt:1822/78775Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T18:49:54.853288Repositório 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 aryl-substituted BODIPY dyes displaying distinct solvatochromic singlet oxygen photosensitization efficiencies
title Synthesis and characterization of aryl-substituted BODIPY dyes displaying distinct solvatochromic singlet oxygen photosensitization efficiencies
spellingShingle Synthesis and characterization of aryl-substituted BODIPY dyes displaying distinct solvatochromic singlet oxygen photosensitization efficiencies
Gonçalves, Raquel C. R.
BODIPY
Intramolecular charge transfer
Photosensitizers
Singlet oxygen
Science & Technology
title_short Synthesis and characterization of aryl-substituted BODIPY dyes displaying distinct solvatochromic singlet oxygen photosensitization efficiencies
title_full Synthesis and characterization of aryl-substituted BODIPY dyes displaying distinct solvatochromic singlet oxygen photosensitization efficiencies
title_fullStr Synthesis and characterization of aryl-substituted BODIPY dyes displaying distinct solvatochromic singlet oxygen photosensitization efficiencies
title_full_unstemmed Synthesis and characterization of aryl-substituted BODIPY dyes displaying distinct solvatochromic singlet oxygen photosensitization efficiencies
title_sort Synthesis and characterization of aryl-substituted BODIPY dyes displaying distinct solvatochromic singlet oxygen photosensitization efficiencies
author Gonçalves, Raquel C. R.
author_facet Gonçalves, Raquel C. R.
Pina, João
Costa, Susana P. G.
Raposo, M. Manuela M.
author_role author
author2 Pina, João
Costa, Susana P. G.
Raposo, M. Manuela M.
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Gonçalves, Raquel C. R.
Pina, João
Costa, Susana P. G.
Raposo, M. Manuela M.
dc.subject.por.fl_str_mv BODIPY
Intramolecular charge transfer
Photosensitizers
Singlet oxygen
Science & Technology
topic BODIPY
Intramolecular charge transfer
Photosensitizers
Singlet oxygen
Science & Technology
description Three BODIPY derivatives substituted at meso position by aryl (phenyl or N,N-dimethylaminonaphthyl) groups and functionalized at position 2 with electron-withdrawing formyl or electron deficient benzimidazole heterocycle were synthesized and completely characterized by the usual spectroscopic techniques. A comprehensive photophysical study showed a remarkable enhancement of the singlet oxygen sensitization quantum yield for meso-substituted dimethylaminonaphthyl BODIPY with the decrease of the dielectric constant of the solvent (0.02–0.04 for dimethylsulfoxide vs. 0.84 in toluene). In toluene the triplet state formation for the aminonaphthyl substituted BODIPY's was found to be mediated by the intramolecular charge transfer state (ICT), whereas in polar solvents triplet state formation is hindered by fast recombination of the ICT state. Pump-probe transient absorption spectroscopy was used to characterize the photoinduced dynamics of the BODIPY derivatives from the femtosecond to the nanosecond time scale.
publishDate 2021
dc.date.none.fl_str_mv 2021-12
2021-12-01T00:00:00Z
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 https://hdl.handle.net/1822/78775
url https://hdl.handle.net/1822/78775
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0143-7208
10.1016/j.dyepig.2021.109784
https://www.sciencedirect.com/science/article/pii/S0143720821006501?via%3Dihub
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
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
repository.mail.fl_str_mv
_version_ 1799132266004217856

Registros relacionados