Photochemistry of 5-Hydroxy-4'-Dimethylaminoflavylium in the presence of SDS micelles. The role of metastable states of flavylium cation-quinoidal base and trans-chalcones

Detalhes bibliográficos
Autor(a) principal: Araújo, Paula
Data de Publicação: 2020
Outros Autores: Mendoza, Johan, Pina, Fernando, Pereira, Ana Rita, Fernandes, Iva, de Freitas, Victor, Oliveira, Joana
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/113070
Resumo: UIDB/50006/2020 UIDP/50006/2020 PTDC/QUI-OUT/29013/2017 SFRH/BD/143309/2019 SFRH/BD/146549/2019 MEX/Ref. 288188 IF/00225/2015
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spelling Photochemistry of 5-Hydroxy-4'-Dimethylaminoflavylium in the presence of SDS micelles. The role of metastable states of flavylium cation-quinoidal base and trans-chalconesAminoflavyliumAnthocyaninsMeta-stabilityPhotochromismQuinoidal baseTrans-ChalconesChemistry(all)Chemical Engineering(all)Physics and Astronomy(all)UIDB/50006/2020 UIDP/50006/2020 PTDC/QUI-OUT/29013/2017 SFRH/BD/143309/2019 SFRH/BD/146549/2019 MEX/Ref. 288188 IF/00225/2015The multistate of species originated by the compound 5-hydroxy-4′-dimethylaminoflavylium was studied in the presence of sodium dodecyl sulfate micelles 0.1 M. A series of pH jumps obtained by addition of base to the equilibrated solutions of the flavylium cation results in a metastable equilibrium between the flavylium cation and the quinoidal base with pKa = 7.6. In neutral to moderately basic medium, only at 60 °C and after 5 days a new distribution involving the flavylium cation and trans-chalcones is achieved. On the other hand, the anionic trans-chalcone can be formed in few minutes in very basic medium at room temperature and from this, another meta-stable state constituted by protonated, neutral and anionic trans-chalcones, pKCt+/Ct = 2.6 and pKCt/Ct- = 10.7 is reached. The equilibrium is apparently attained between flavylium cation, neutral and anionic trans-chalcones respectively for pKAH+/Ct = 4.1 and pKCt/Ct- = 10.7. Irradiation of the neutral (stable or metastable) and protonated (meta-stable) trans-chalcones yields to the appearance of the quinoidal base or the flavylium cation in an extended pH region 1 < pH < 10. The peculiar properties of this flavylium based photochromic system are explained by means of an energy level diagram where cis-chalcone and hemiketal lay above the quinoidal base.DQ - Departamento de QuímicaLAQV@REQUIMTERUNAraújo, PaulaMendoza, JohanPina, FernandoPereira, Ana RitaFernandes, Ivade Freitas, VictorOliveira, Joana2022-03-24T01:31:13Z2020-11-012020-11-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10362/113070eng1010-6030PURE: 28245706https://doi.org/10.1016/j.jphotochem.2020.112827info: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:RCAAP2024-03-11T04:56:19Zoai:run.unl.pt:10362/113070Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:42:16.034037Repositório 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 Photochemistry of 5-Hydroxy-4'-Dimethylaminoflavylium in the presence of SDS micelles. The role of metastable states of flavylium cation-quinoidal base and trans-chalcones
title Photochemistry of 5-Hydroxy-4'-Dimethylaminoflavylium in the presence of SDS micelles. The role of metastable states of flavylium cation-quinoidal base and trans-chalcones
spellingShingle Photochemistry of 5-Hydroxy-4'-Dimethylaminoflavylium in the presence of SDS micelles. The role of metastable states of flavylium cation-quinoidal base and trans-chalcones
Araújo, Paula
Aminoflavylium
Anthocyanins
Meta-stability
Photochromism
Quinoidal base
Trans-Chalcones
Chemistry(all)
Chemical Engineering(all)
Physics and Astronomy(all)
title_short Photochemistry of 5-Hydroxy-4'-Dimethylaminoflavylium in the presence of SDS micelles. The role of metastable states of flavylium cation-quinoidal base and trans-chalcones
title_full Photochemistry of 5-Hydroxy-4'-Dimethylaminoflavylium in the presence of SDS micelles. The role of metastable states of flavylium cation-quinoidal base and trans-chalcones
title_fullStr Photochemistry of 5-Hydroxy-4'-Dimethylaminoflavylium in the presence of SDS micelles. The role of metastable states of flavylium cation-quinoidal base and trans-chalcones
title_full_unstemmed Photochemistry of 5-Hydroxy-4'-Dimethylaminoflavylium in the presence of SDS micelles. The role of metastable states of flavylium cation-quinoidal base and trans-chalcones
title_sort Photochemistry of 5-Hydroxy-4'-Dimethylaminoflavylium in the presence of SDS micelles. The role of metastable states of flavylium cation-quinoidal base and trans-chalcones
author Araújo, Paula
author_facet Araújo, Paula
Mendoza, Johan
Pina, Fernando
Pereira, Ana Rita
Fernandes, Iva
de Freitas, Victor
Oliveira, Joana
author_role author
author2 Mendoza, Johan
Pina, Fernando
Pereira, Ana Rita
Fernandes, Iva
de Freitas, Victor
Oliveira, Joana
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv DQ - Departamento de Química
LAQV@REQUIMTE
RUN
dc.contributor.author.fl_str_mv Araújo, Paula
Mendoza, Johan
Pina, Fernando
Pereira, Ana Rita
Fernandes, Iva
de Freitas, Victor
Oliveira, Joana
dc.subject.por.fl_str_mv Aminoflavylium
Anthocyanins
Meta-stability
Photochromism
Quinoidal base
Trans-Chalcones
Chemistry(all)
Chemical Engineering(all)
Physics and Astronomy(all)
topic Aminoflavylium
Anthocyanins
Meta-stability
Photochromism
Quinoidal base
Trans-Chalcones
Chemistry(all)
Chemical Engineering(all)
Physics and Astronomy(all)
description UIDB/50006/2020 UIDP/50006/2020 PTDC/QUI-OUT/29013/2017 SFRH/BD/143309/2019 SFRH/BD/146549/2019 MEX/Ref. 288188 IF/00225/2015
publishDate 2020
dc.date.none.fl_str_mv 2020-11-01
2020-11-01T00:00:00Z
2022-03-24T01:31:13Z
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/10362/113070
url http://hdl.handle.net/10362/113070
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1010-6030
PURE: 28245706
https://doi.org/10.1016/j.jphotochem.2020.112827
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.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
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