Solvent and Media Effects on the Photophysics of Naphthoxazole Derivatives
Author
dc.contributor.author
Curitol, Manuel
Author
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Ragas, Xavier
es_CL
Author
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Nonell, Santi
es_CL
Author
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Pizarro, Nancy
es_CL
Author
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Encinas, María V.
es_CL
Author
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Rojas, Pedro
es_CL
Author
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Zanocco, Renzo P.
es_CL
Author
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Lemp Miranda, Else
es_CL
Author
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Günther Sapunar, Germán
es_CL
Author
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Zanocco Loyola, Antonio
es_CL
Admission date
dc.date.accessioned
2014-01-10T18:47:46Z
Available date
dc.date.available
2014-01-10T18:47:46Z
Publication date
dc.date.issued
2013
Cita de ítem
dc.identifier.citation
Photochemistry and Photobiology, 2013, 89: 1327–1334
en_US
Identifier
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DOI: 10.1111/php.12133
Identifier
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https://repositorio.uchile.cl/handle/2250/121744
General note
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Artículo de publicación ISI
en_US
Abstract
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The photophysical properties of 2-phenyl-naphtho[1,2-d][1,3]
oxazole, 2(4-N,N-dimethylaminophenyl)naphtho[1,2-d][1,3]
oxazole and 2(4-N,N-diphenylaminophenyl) naphtho[1,2-d]
[1,3]oxazole were studied in a series of solvents. UV–Vis
absorption spectra are insensitive to solvent polarity whereas
the fluorescence spectra in the same solvent set show an
important solvatochromic effect leading to large Stokes shifts.
Linear solvation energy relationships were employed to correlate
the position of fluorescence spectra maxima with
microscopic empirical solvent parameters. This study indicates
that important intramolecular charge transfer takes
place during the excitation process. In addition, an analysis
of the solvatochromic behavior of the UV–Vis absorption and
fluorescence spectra in terms of the Lippert–Mataga equation
shows a large increase in the excited-state dipole moment,
which is also compatible with the formation of an intramolecular
charge-transfer excited state. We propose both naphthoxazole
derivatives as suitable fluorescent probes to
determine physicochemical microproperties in several systems
and as dyes in dye lasers; consequence of their high fluorescence
quantum yields in most solvents, their large molar
absorption coefficients, with fluorescence lifetimes in the
range 1–3 ns as well as their high photostability.