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dc.contributor.author
Cardoso Dilelio, Marina
dc.contributor.author
Kaufman, Teodoro Saul
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dc.contributor.author
Almeida Iglesias, Bernardo
dc.contributor.author
Silveira, Claudio
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dc.date.available
2022-10-04T17:49:11Z
dc.date.issued
2022-02
dc.identifier.citation
Cardoso Dilelio, Marina; Kaufman, Teodoro Saul; Almeida Iglesias, Bernardo; Silveira, Claudio; Synthesis and evaluation of photophysical and electrochemical properties of vinyl chalcogenide derivatives of phenothiazines; Elsevier; Dyes and Pigments; 198; 2-2022; 1-13
dc.identifier.issn
0143-7208
dc.identifier.uri
http://hdl.handle.net/11336/171788
dc.description.abstract
The Wittig-Horner mediated syntheses of phenothiazines carrying vinylsulfide and vinylselenide motifs attached to the aromatic ring(s) or connected to the central nitrogen atom of the heterocycle, and the subsequent study of their photophysical and electrochemical properties, are reported. These compounds were obtained as mixtures of geometric isomers, in good to excellent yields. To complete the study, a small set of vinylsulfoxide and vinylsulfone derivatives was also prepared from the corresponding oxidized phosphinoxides. The photophysical properties of the compounds were examined in solvents of varying polarity, in which they presented absorption maxima in the UV region, with molar absorptivity coefficients compatible with symmetry-allowed π–π* electronic transitions. The heterocyclic derivatives were fluorescent. Compounds bearing vinylsulfide moieties associated to the nitrogen atom of the heterocycle displayed less intense fluorescence than the phenothiazine derivatives carrying vinylchalcogenides bonded to the aromatic ring; the latter also exhibited more red-shifted absorption spectra, and Stokes shifts in the range 6115–8170 cm−1 with weak dependence of solvent polarity. The sulfoxide and sulfones displayed more red-shifted spectra than the corresponding sulfides. The cyclic voltammograms of all derivatives exhibited a common pattern of reversible or quasi-reversible processes in the anodic region, related to the phenothiazine unit.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Elsevier
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dc.rights
info:eu-repo/semantics/restrictedAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
ELECTROCHEMICAL CHARACTERISTICS
dc.subject
PHENOTHIAZINE DERIVATIVES
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PHOTOPHYSICAL PROPERTIES
dc.subject
VINYLCHALCOGENIDES
dc.subject.classification
Química Orgánica
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dc.subject.classification
Ciencias Químicas
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dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
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dc.title
Synthesis and evaluation of photophysical and electrochemical properties of vinyl chalcogenide derivatives of phenothiazines
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2022-07-04T19:59:38Z
dc.journal.volume
198
dc.journal.pagination
1-13
dc.journal.pais
Países Bajos
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dc.journal.ciudad
Amsterdam
dc.description.fil
Fil: Cardoso Dilelio, Marina. Universidade Federal de Santa Maria; Brasil
dc.description.fil
Fil: Kaufman, Teodoro Saul. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
dc.description.fil
Fil: Almeida Iglesias, Bernardo. Universidade Federal de Santa Maria; Brasil
dc.description.fil
Fil: Silveira, Claudio. Universidade Federal de Santa Maria; Brasil
dc.journal.title
Dyes and Pigments
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dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S0143720821008482
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1016/j.dyepig.2021.109982
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