Photophysical properties of coumarin compounds in neat and binary solvent mixtures: evaluation and correlation between solvatochromism and solvent polarity parameters
Autor(a) principal: | |
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Data de Publicação: | 2014 |
Outros Autores: | , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNIFESP |
Texto Completo: | http://dx.doi.org/10.5935/0103-5053.20140051 http://repositorio.unifesp.br/handle/11600/8370 |
Resumo: | This work studied the fluorescent and solvatochromic properties of coumarin and its derivatives aiming to contribute in the elucidation of the excited state behavior of the molecule in solvent mixtures. This approach has been developed through a set of measurements involving different solvent ratios, which present distinct dielectric constants. The excitation and fluorescence maxima were largely blue-shifted with increasing participation of the organic solvent and the Stokes shifts were unusually low in mixtures with lower solvent polarity parameter, Δf. The emission intensity of coumarin was extremely sensitive to the polarity and the different structural conformations of solvents. These results influenced the spectroscopic behavior and explain the deviation from the linearity of the Lippert-Mataga relationship. The use of fluorescence spectroscopy makes the understanding of the behavior of the systems studied when in the presence of different environments being extremely important for the identification and characterization of coumarin in different pharmaceutical formulations. |
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Photophysical properties of coumarin compounds in neat and binary solvent mixtures: evaluation and correlation between solvatochromism and solvent polarity parameterscoumarinfluorescencesolvatochromic propertiesemission spectraexcitation spectraThis work studied the fluorescent and solvatochromic properties of coumarin and its derivatives aiming to contribute in the elucidation of the excited state behavior of the molecule in solvent mixtures. This approach has been developed through a set of measurements involving different solvent ratios, which present distinct dielectric constants. The excitation and fluorescence maxima were largely blue-shifted with increasing participation of the organic solvent and the Stokes shifts were unusually low in mixtures with lower solvent polarity parameter, Δf. The emission intensity of coumarin was extremely sensitive to the polarity and the different structural conformations of solvents. These results influenced the spectroscopic behavior and explain the deviation from the linearity of the Lippert-Mataga relationship. The use of fluorescence spectroscopy makes the understanding of the behavior of the systems studied when in the presence of different environments being extremely important for the identification and characterization of coumarin in different pharmaceutical formulations.Este trabalho estuda as propriedades fluorescentes e solvatocrômicas da cumarina e seus derivados visando contribuir na elucidação do comportamento do estado excitado dessas moléculas em misturas de solventes. Esta abordagem foi desenvolvida através de medidas que envolveram diferentes relações de solventes com constantes dielétricas distintas. Os máximos de excitação e emissão de fluorescência foram deslocados para o azul nas misturas com maior proporção do solvente orgânico e o deslocamento de Stokes foi menor em misturas com menor parâmetro de polaridade do solvente, Δf. A intensidade de emissão de cumarina foi extremamente sensível à polaridade e às diferentes conformações estruturais dos solventes. Estas conformações influenciaram diretamente no comportamento espectroscópico e explicam o desvio da linearidade da relação de Lippert-Mataga. A utilização de espectroscopia de fluorescência possibilita o conhecimento do comportamento destes derivados quando em diferentes ambientes, sendo de extrema importância para a identificação e caracterização desses compostos em formulações farmacêuticas.Universidade Federal de São João Del Rei Departamento de ZootecniaUniversidade do Vale do Paraíba Instituto de Pesquisa e DesenvolvimentoUniversidade Federal de São João Del Rei Departamento de Ciências NaturaisUniversidade Federal do ABC Centro de Engenharia, Modelagem e Ciências Sociais AplicadasUniversidade Federal de São Paulo (UNIFESP) Departamento de Ciências Exatas e da TerraUniversidade Federal de Pelotas Centro de Ciências Químicas, Farmacêuticas e de AlimentosUniversidade Federal do ABC Centro de Ciências Naturais e HumanasUNIFESP, Depto. de Ciências Exatas e da TerraSciELOL'Oreal/Academia Brasileira de Ciencias/Unesco (Grant for Women in Science)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)479655/2008-1 e 474019/2012-808/50588-6 e 06/56701-3Sociedade Brasileira de QuímicaUniversidade Federal de São João Del Rei Departamento de ZootecniaUniversidade do Vale do Paraíba Instituto de Pesquisa e DesenvolvimentoUniversidade Federal de São João Del Rei Departamento de Ciências NaturaisUniversidade Federal do ABC Centro de Engenharia, Modelagem e Ciências Sociais AplicadasUniversidade Federal de São Paulo (UNIFESP)Universidade Federal de Pelotas Centro de Ciências Químicas, Farmacêuticas e de AlimentosUniversidade Federal do ABC Centro de Ciências Naturais e HumanasMoreira, Leonardo MarmoMelo, Mirian M. deMartins, Priscila A.Lyon, Juliana PereiraRomani, Ana PaulaCodognoto, Lucia [UNIFESP]Santos, Sandra C. dosOliveira, Hueder Paulo Moisés de2015-06-14T13:47:05Z2015-06-14T13:47:05Z2014-05-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersion873-881application/pdfhttp://dx.doi.org/10.5935/0103-5053.20140051Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 25, n. 5, p. 873-881, 2014.10.5935/0103-5053.20140051S0103-50532014000500009.pdf0103-50531678-4790S0103-50532014000500009http://repositorio.unifesp.br/handle/11600/8370WOS:000335817400009engJournal of the Brazilian Chemical Societyinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UNIFESPinstname:Universidade Federal de São Paulo (UNIFESP)instacron:UNIFESP2024-07-29T02:09:03Zoai:repositorio.unifesp.br/:11600/8370Repositório InstitucionalPUBhttp://www.repositorio.unifesp.br/oai/requestbiblioteca.csp@unifesp.bropendoar:34652024-07-29T02:09:03Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)false |
dc.title.none.fl_str_mv |
Photophysical properties of coumarin compounds in neat and binary solvent mixtures: evaluation and correlation between solvatochromism and solvent polarity parameters |
title |
Photophysical properties of coumarin compounds in neat and binary solvent mixtures: evaluation and correlation between solvatochromism and solvent polarity parameters |
spellingShingle |
Photophysical properties of coumarin compounds in neat and binary solvent mixtures: evaluation and correlation between solvatochromism and solvent polarity parameters Moreira, Leonardo Marmo coumarin fluorescence solvatochromic properties emission spectra excitation spectra |
title_short |
Photophysical properties of coumarin compounds in neat and binary solvent mixtures: evaluation and correlation between solvatochromism and solvent polarity parameters |
title_full |
Photophysical properties of coumarin compounds in neat and binary solvent mixtures: evaluation and correlation between solvatochromism and solvent polarity parameters |
title_fullStr |
Photophysical properties of coumarin compounds in neat and binary solvent mixtures: evaluation and correlation between solvatochromism and solvent polarity parameters |
title_full_unstemmed |
Photophysical properties of coumarin compounds in neat and binary solvent mixtures: evaluation and correlation between solvatochromism and solvent polarity parameters |
title_sort |
Photophysical properties of coumarin compounds in neat and binary solvent mixtures: evaluation and correlation between solvatochromism and solvent polarity parameters |
author |
Moreira, Leonardo Marmo |
author_facet |
Moreira, Leonardo Marmo Melo, Mirian M. de Martins, Priscila A. Lyon, Juliana Pereira Romani, Ana Paula Codognoto, Lucia [UNIFESP] Santos, Sandra C. dos Oliveira, Hueder Paulo Moisés de |
author_role |
author |
author2 |
Melo, Mirian M. de Martins, Priscila A. Lyon, Juliana Pereira Romani, Ana Paula Codognoto, Lucia [UNIFESP] Santos, Sandra C. dos Oliveira, Hueder Paulo Moisés de |
author2_role |
author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Federal de São João Del Rei Departamento de Zootecnia Universidade do Vale do Paraíba Instituto de Pesquisa e Desenvolvimento Universidade Federal de São João Del Rei Departamento de Ciências Naturais Universidade Federal do ABC Centro de Engenharia, Modelagem e Ciências Sociais Aplicadas Universidade Federal de São Paulo (UNIFESP) Universidade Federal de Pelotas Centro de Ciências Químicas, Farmacêuticas e de Alimentos Universidade Federal do ABC Centro de Ciências Naturais e Humanas |
dc.contributor.author.fl_str_mv |
Moreira, Leonardo Marmo Melo, Mirian M. de Martins, Priscila A. Lyon, Juliana Pereira Romani, Ana Paula Codognoto, Lucia [UNIFESP] Santos, Sandra C. dos Oliveira, Hueder Paulo Moisés de |
dc.subject.por.fl_str_mv |
coumarin fluorescence solvatochromic properties emission spectra excitation spectra |
topic |
coumarin fluorescence solvatochromic properties emission spectra excitation spectra |
description |
This work studied the fluorescent and solvatochromic properties of coumarin and its derivatives aiming to contribute in the elucidation of the excited state behavior of the molecule in solvent mixtures. This approach has been developed through a set of measurements involving different solvent ratios, which present distinct dielectric constants. The excitation and fluorescence maxima were largely blue-shifted with increasing participation of the organic solvent and the Stokes shifts were unusually low in mixtures with lower solvent polarity parameter, Δf. The emission intensity of coumarin was extremely sensitive to the polarity and the different structural conformations of solvents. These results influenced the spectroscopic behavior and explain the deviation from the linearity of the Lippert-Mataga relationship. The use of fluorescence spectroscopy makes the understanding of the behavior of the systems studied when in the presence of different environments being extremely important for the identification and characterization of coumarin in different pharmaceutical formulations. |
publishDate |
2014 |
dc.date.none.fl_str_mv |
2014-05-01 2015-06-14T13:47:05Z 2015-06-14T13:47:05Z |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.5935/0103-5053.20140051 Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 25, n. 5, p. 873-881, 2014. 10.5935/0103-5053.20140051 S0103-50532014000500009.pdf 0103-5053 1678-4790 S0103-50532014000500009 http://repositorio.unifesp.br/handle/11600/8370 WOS:000335817400009 |
url |
http://dx.doi.org/10.5935/0103-5053.20140051 http://repositorio.unifesp.br/handle/11600/8370 |
identifier_str_mv |
Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 25, n. 5, p. 873-881, 2014. 10.5935/0103-5053.20140051 S0103-50532014000500009.pdf 0103-5053 1678-4790 S0103-50532014000500009 WOS:000335817400009 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Journal of the Brazilian Chemical Society |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
873-881 application/pdf |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
reponame:Repositório Institucional da UNIFESP instname:Universidade Federal de São Paulo (UNIFESP) instacron:UNIFESP |
instname_str |
Universidade Federal de São Paulo (UNIFESP) |
instacron_str |
UNIFESP |
institution |
UNIFESP |
reponame_str |
Repositório Institucional da UNIFESP |
collection |
Repositório Institucional da UNIFESP |
repository.name.fl_str_mv |
Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP) |
repository.mail.fl_str_mv |
biblioteca.csp@unifesp.br |
_version_ |
1814268295182811136 |