Tryptanthrin derivatives as efficient singlet oxygen sensitizers
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/10316/107457 https://doi.org/10.1007/s43630-021-00117-8 |
Resumo: | Halogenated tryptanthrin and aminotryptanthrin were synthesized from indigo or isatin precursors. Dibromo- and tetrabromotryptanthrin were obtained from indigo dyes following green chemistry procedures, through microwave-assisted synthesis in mild oxidation conditions. Spectral and photophysical properties of the compounds, including quantitative determination of all the different deactivation pathways of S1 and T1, were obtained in different solvents and temperatures. The triplet state ( T1) has a dominant role on the photophysical properties of these compounds, which is further enhanced by the halogens at the fused-phenyl rings. Substitution with an amino group, 2-aminotryptanthrin (TRYP-NH2), leads a dominance of the radiative decay channel. Moreover, with the sole exception of TRYP-NH2, S1 ~ ~ > T1 intersystem crossing constitutes the dominant route, with internal conversion playing a minor role in the deactivation of S1 in all the studied derivatives. In agreement with tryptanthrin, emission of the triplet state of tryptanthrin derivatives (with exception of TRYP-NH2), was observed together with an enhancement of the singlet oxygen sensitization quantum yield: from 70% in tryptanthrin to 92% in the iodine derivative. This strongly contrasts with indigo and its derivatives, where singlet oxygen sensitization is found inefficient. |
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Tryptanthrin derivatives as efficient singlet oxygen sensitizersTryptanthrinTryptanthrin derivativesFluorescenceSinglet oxygen sensitizationHalogenated tryptanthrin and aminotryptanthrin were synthesized from indigo or isatin precursors. Dibromo- and tetrabromotryptanthrin were obtained from indigo dyes following green chemistry procedures, through microwave-assisted synthesis in mild oxidation conditions. Spectral and photophysical properties of the compounds, including quantitative determination of all the different deactivation pathways of S1 and T1, were obtained in different solvents and temperatures. The triplet state ( T1) has a dominant role on the photophysical properties of these compounds, which is further enhanced by the halogens at the fused-phenyl rings. Substitution with an amino group, 2-aminotryptanthrin (TRYP-NH2), leads a dominance of the radiative decay channel. Moreover, with the sole exception of TRYP-NH2, S1 ~ ~ > T1 intersystem crossing constitutes the dominant route, with internal conversion playing a minor role in the deactivation of S1 in all the studied derivatives. In agreement with tryptanthrin, emission of the triplet state of tryptanthrin derivatives (with exception of TRYP-NH2), was observed together with an enhancement of the singlet oxygen sensitization quantum yield: from 70% in tryptanthrin to 92% in the iodine derivative. This strongly contrasts with indigo and its derivatives, where singlet oxygen sensitization is found inefficient.Springer2021info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/107457http://hdl.handle.net/10316/107457https://doi.org/10.1007/s43630-021-00117-8eng1474-9092Pinheiro, DanielaPineiro, MartaSeixas de Melo, J. Sérgioinfo: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:RCAAP2023-07-18T08:09:31Zoai:estudogeral.uc.pt:10316/107457Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:23:48.618363Repositório 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 |
Tryptanthrin derivatives as efficient singlet oxygen sensitizers |
title |
Tryptanthrin derivatives as efficient singlet oxygen sensitizers |
spellingShingle |
Tryptanthrin derivatives as efficient singlet oxygen sensitizers Pinheiro, Daniela Tryptanthrin Tryptanthrin derivatives Fluorescence Singlet oxygen sensitization |
title_short |
Tryptanthrin derivatives as efficient singlet oxygen sensitizers |
title_full |
Tryptanthrin derivatives as efficient singlet oxygen sensitizers |
title_fullStr |
Tryptanthrin derivatives as efficient singlet oxygen sensitizers |
title_full_unstemmed |
Tryptanthrin derivatives as efficient singlet oxygen sensitizers |
title_sort |
Tryptanthrin derivatives as efficient singlet oxygen sensitizers |
author |
Pinheiro, Daniela |
author_facet |
Pinheiro, Daniela Pineiro, Marta Seixas de Melo, J. Sérgio |
author_role |
author |
author2 |
Pineiro, Marta Seixas de Melo, J. Sérgio |
author2_role |
author author |
dc.contributor.author.fl_str_mv |
Pinheiro, Daniela Pineiro, Marta Seixas de Melo, J. Sérgio |
dc.subject.por.fl_str_mv |
Tryptanthrin Tryptanthrin derivatives Fluorescence Singlet oxygen sensitization |
topic |
Tryptanthrin Tryptanthrin derivatives Fluorescence Singlet oxygen sensitization |
description |
Halogenated tryptanthrin and aminotryptanthrin were synthesized from indigo or isatin precursors. Dibromo- and tetrabromotryptanthrin were obtained from indigo dyes following green chemistry procedures, through microwave-assisted synthesis in mild oxidation conditions. Spectral and photophysical properties of the compounds, including quantitative determination of all the different deactivation pathways of S1 and T1, were obtained in different solvents and temperatures. The triplet state ( T1) has a dominant role on the photophysical properties of these compounds, which is further enhanced by the halogens at the fused-phenyl rings. Substitution with an amino group, 2-aminotryptanthrin (TRYP-NH2), leads a dominance of the radiative decay channel. Moreover, with the sole exception of TRYP-NH2, S1 ~ ~ > T1 intersystem crossing constitutes the dominant route, with internal conversion playing a minor role in the deactivation of S1 in all the studied derivatives. In agreement with tryptanthrin, emission of the triplet state of tryptanthrin derivatives (with exception of TRYP-NH2), was observed together with an enhancement of the singlet oxygen sensitization quantum yield: from 70% in tryptanthrin to 92% in the iodine derivative. This strongly contrasts with indigo and its derivatives, where singlet oxygen sensitization is found inefficient. |
publishDate |
2021 |
dc.date.none.fl_str_mv |
2021 |
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/10316/107457 http://hdl.handle.net/10316/107457 https://doi.org/10.1007/s43630-021-00117-8 |
url |
http://hdl.handle.net/10316/107457 https://doi.org/10.1007/s43630-021-00117-8 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
1474-9092 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Springer |
publisher.none.fl_str_mv |
Springer |
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 |
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RCAAP |
reponame_str |
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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1799134124441600000 |