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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

2020-11-01Artigo científico Acesso aberto
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dc.contributor.authorAraújo, Paula
dc.contributor.authorMendoza, Johan
dc.contributor.authorPina, Fernando
dc.contributor.authorPereira, Ana Rita
dc.contributor.authorFernandes, Iva
dc.contributor.authorde Freitas, Victor
dc.contributor.authorOliveira, Joana
dc.contributor.institutionDQ - Departamento de Química
dc.contributor.institutionLAQV@REQUIMTE
dc.contributor.pblElsevier
dc.date.accessioned2021-03-04T00:00:54Z
dc.date.available2022-03-24T01:31:13Z
dc.date.embargoedUntil2021-11-01
dc.date.issued2020-11-01
dc.descriptionUIDB/50006/2020 UIDP/50006/2020 PTDC/QUI-OUT/29013/2017 SFRH/BD/143309/2019 SFRH/BD/146549/2019 MEX/Ref. 288188 IF/00225/2015
dc.description.abstractThe 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.en
dc.description.versionauthorsversion
dc.description.versionpublished
dc.format.extent3109408
dc.identifier.doi10.1016/j.jphotochem.2020.112827
dc.identifier.issn1010-6030
dc.identifier.otherPURE: 28245706
dc.identifier.otherPURE UUID: 89b72784-acd9-480f-9604-0752b5c8fcdb
dc.identifier.otherScopus: 85089233526
dc.identifier.otherWOS: 000582481800022
dc.identifier.otherORCID: /0000-0001-8529-6848/work/89319490
dc.identifier.urihttp://hdl.handle.net/10362/113070
dc.identifier.urlhttps://www.scopus.com/pages/publications/85089233526
dc.language.isoeng
dc.peerreviewedyes
dc.relationinfo:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F86173%2F2012/PT
dc.relationSÍNTESE E CARACTERIZAÇÃO ESTRUTURAL DE PIGMENTOS ANTOCIÂNICOS E RESPETIVOS METABOLITOS: BIODISPONIBILIDADE E PROPRIEDADES BIOLÓGICAS.
dc.subjectAminoflavylium
dc.subjectAnthocyanins
dc.subjectMeta-stability
dc.subjectPhotochromism
dc.subjectQuinoidal base
dc.subjectTrans-Chalcones
dc.subjectGeneral Chemistry
dc.subjectGeneral Chemical Engineering
dc.subjectGeneral Physics and Astronomy
dc.titlePhotochemistry of 5-Hydroxy-4'-Dimethylaminoflavylium in the presence of SDS micelles. The role of metastable states of flavylium cation-quinoidal base and trans-chalconesen
dc.typejournal article
degois.publication.titleJournal of Photochemistry and Photobiology A: Chemistry
degois.publication.volume402
dspace.entity.typePublication
oaire.awardNumberSFRH/BPD/86173/2012
oaire.awardTitleSÍNTESE E CARACTERIZAÇÃO ESTRUTURAL DE PIGMENTOS ANTOCIÂNICOS E RESPETIVOS METABOLITOS: BIODISPONIBILIDADE E PROPRIEDADES BIOLÓGICAS.
oaire.awardURIinfo:eu-repo/grantAgreement/FCT//SFRH%2FBPD%2F86173%2F2012/PT
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccess
relation.isProjectOfPublicationc3feec27-8a4b-4a6a-b4f1-11f7f98ea785
relation.isProjectOfPublication.latestForDiscoveryc3feec27-8a4b-4a6a-b4f1-11f7f98ea785

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