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Photochemical reactions of halogenated aromatic 1,3-diketones in solution studied by steady state, one- and two-color laser flash photolyses

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Photochemical reactions of halogenated aromatic 1,3-diketones in solution studied by steady state, one- and two-color laser flash photolyses

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dc.contributor.author Yamaji, Minoru es_ES
dc.contributor.author Suwa, Yuri es_ES
dc.contributor.author Shimokawa, Rieko es_ES
dc.contributor.author Paris, Cecilia es_ES
dc.contributor.author Miranda Alonso, Miguel Ángel es_ES
dc.date.accessioned 2020-10-07T03:33:32Z
dc.date.available 2020-10-07T03:33:32Z
dc.date.issued 2015 es_ES
dc.identifier.issn 1474-905X es_ES
dc.identifier.uri http://hdl.handle.net/10251/151279
dc.description.abstract Photochemical processes of 4-tert-butyl-4'-methoxydibenzoylmethane (Avobenzone, AB), 4-phenylbenzoylbenzoyl-, 4-phenylbenzoyl-2'-furanyl- and 4-phenylbenzoyl-2'-thenoylmethanes (PB@Ph, PB@F and PB@T, respectively) substituted with Br and Cl at the C2 position were studied by stationary and laser flash photolyses in solution. The absorption spectral features showed that the molecular structures of the halogenated diketones are in the keto forms while those of halogen-free diketones are in the enol forms. The excited singlet and triplet state energies were determined from the absorption and emission spectra. From the absorption spectral changes upon steady state photolysis of brominated diketones in ethanol, the corresponding halogen-free diketones were formed due to Br elimination being the major photochemical process. The determined quantum yields for the formation of the halogen-free diketones were independent of the amount of dissolved oxygen, indicating that the elimination process is an event in the excited singlet (S-1) states. In contrast, from the observed absorption spectra obtained upon photolysis of chlorinated AB and PB@Ph, it was inferred that Norrish type I is the major photochemical reaction in the S-1 states in acetonitrile. Chlorinated PB@F and PB@T were found to undergo Cl elimination in the S-1 states in cyclohexane to form the corresponding halogen-free diketones. Laser photolysis studies of brominated AB in acetonitrile and ethanol provided a transient absorption spectrum ascribable to the Avobenzone radical (ABR) produced by debromination as the initial intermediate, followed by the AB formation in ethanol. The quenching rate constant of ABR by ethanol and the quantum yield of the AB formation via ABR were determined. These observations provided evidence that H-atom abstraction of ABR from ethanol is responsible for the AB formation. Conversely, laser flash photolysis of brominated and chlorinated PB@Ph, PB@F and PB@T demonstrated the formation of the triplet-triplet absorption spectra. No chemical reactions were found to occur in the triplet (T-1) states. Two-color two-laser photolysis studies were carried out on the T-1 state of chlorinated PB@Ph, PB@F and PB@T, resulting in the formation of the corresponding halogen-free diketones. These observations confirmed the occurrence of Cl elimination in the highly excited triplet (T-n, n >= 2) states. Based on the computed bond dissociation energies for the C-halogen and C-C bonds, switching mechanisms of dehalogenation and alpha-cleavage were discussed. es_ES
dc.description.sponsorship This work has been supported by a Grant-in-Aid for Scientific Research (26288032) from the Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japanese Government. MY thanks Cosmetrogy Foundation for the financial support. Prof. Teruo Shinmyozu and Dr Kenta Goto at Kyusyu University are acknowledged for performing the mass spectroscopy of PP<INF>253</INF> and PP<INF>283</INF>. es_ES
dc.language Inglés es_ES
dc.publisher The Royal Society of Chemistry es_ES
dc.relation MEXT/26288032 es_ES
dc.relation.ispartof Photochemical & Photobiological Sciences es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject.classification QUIMICA ORGANICA es_ES
dc.title Photochemical reactions of halogenated aromatic 1,3-diketones in solution studied by steady state, one- and two-color laser flash photolyses es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1039/c5pp00211g es_ES
dc.rights.accessRights Abierto es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Química - Departament de Química es_ES
dc.contributor.affiliation Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química es_ES
dc.description.bibliographicCitation Yamaji, M.; Suwa, Y.; Shimokawa, R.; Paris, C.; Miranda Alonso, MÁ. (2015). Photochemical reactions of halogenated aromatic 1,3-diketones in solution studied by steady state, one- and two-color laser flash photolyses. Photochemical & Photobiological Sciences. 14(9):1673-1684. https://doi.org/10.1039/c5pp00211g es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1039/c5pp00211g es_ES
dc.description.upvformatpinicio 1673 es_ES
dc.description.upvformatpfin 1684 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 14 es_ES
dc.description.issue 9 es_ES
dc.identifier.pmid 26147877 es_ES
dc.relation.pasarela S\309956 es_ES
dc.contributor.funder Ministry of Education, Culture, Sports, Science and Technology, Japón es_ES
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