Solvent and media effects on the photophysics of naphthoxazole derivatives

Manuel Curitol, Xavier Ragas, Santi Nonell, Nancy Pizarro, María V. Encinas, Pedro Rojas, Renzo P. Zanocco, Else Lemp, Germán Günther, Antonio L. Zanocco

Resultado de la investigación: Article

3 Citas (Scopus)

Resumen

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.

Idioma originalEnglish
Páginas (desde-hasta)1327-1334
Número de páginas8
PublicaciónPhotochemistry and Photobiology
Volumen89
N.º6
DOI
EstadoPublished - 1 nov 2013

Huella dactilar

Oxazoles
oxazole
Fluorescence
Derivatives
fluorescence
Excited states
Charge transfer
charge transfer
excitation
absorption spectra
Dye Lasers
Dye lasers
Solvation
Dipole moment
Quantum yield
Fluorescent Dyes
dye lasers
solvation
Absorption spectra
absorptivity

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry

Citar esto

Curitol, M., Ragas, X., Nonell, S., Pizarro, N., Encinas, M. V., Rojas, P., ... Zanocco, A. L. (2013). Solvent and media effects on the photophysics of naphthoxazole derivatives. Photochemistry and Photobiology, 89(6), 1327-1334. https://doi.org/10.1111/php.12133
Curitol, Manuel ; Ragas, Xavier ; Nonell, Santi ; Pizarro, Nancy ; Encinas, María V. ; Rojas, Pedro ; Zanocco, Renzo P. ; Lemp, Else ; Günther, Germán ; Zanocco, Antonio L. / Solvent and media effects on the photophysics of naphthoxazole derivatives. En: Photochemistry and Photobiology. 2013 ; Vol. 89, N.º 6. pp. 1327-1334.
@article{0412e206238048ee81c17fe221142c68,
title = "Solvent and media effects on the photophysics of naphthoxazole derivatives",
abstract = "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.",
author = "Manuel Curitol and Xavier Ragas and Santi Nonell and Nancy Pizarro and Encinas, {Mar{\'i}a V.} and Pedro Rojas and Zanocco, {Renzo P.} and Else Lemp and Germ{\'a}n G{\"u}nther and Zanocco, {Antonio L.}",
year = "2013",
month = "11",
day = "1",
doi = "10.1111/php.12133",
language = "English",
volume = "89",
pages = "1327--1334",
journal = "Photochemistry and Photobiology",
issn = "0031-8655",
publisher = "Wiley-Blackwell",
number = "6",

}

Curitol, M, Ragas, X, Nonell, S, Pizarro, N, Encinas, MV, Rojas, P, Zanocco, RP, Lemp, E, Günther, G & Zanocco, AL 2013, 'Solvent and media effects on the photophysics of naphthoxazole derivatives', Photochemistry and Photobiology, vol. 89, n.º 6, pp. 1327-1334. https://doi.org/10.1111/php.12133

Solvent and media effects on the photophysics of naphthoxazole derivatives. / Curitol, Manuel; Ragas, Xavier; Nonell, Santi; Pizarro, Nancy; Encinas, María V.; Rojas, Pedro; Zanocco, Renzo P.; Lemp, Else; Günther, Germán; Zanocco, Antonio L.

En: Photochemistry and Photobiology, Vol. 89, N.º 6, 01.11.2013, p. 1327-1334.

Resultado de la investigación: Article

TY - JOUR

T1 - Solvent and media effects on the photophysics of naphthoxazole derivatives

AU - Curitol, Manuel

AU - Ragas, Xavier

AU - Nonell, Santi

AU - Pizarro, Nancy

AU - Encinas, María V.

AU - Rojas, Pedro

AU - Zanocco, Renzo P.

AU - Lemp, Else

AU - Günther, Germán

AU - Zanocco, Antonio L.

PY - 2013/11/1

Y1 - 2013/11/1

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=84887376105&partnerID=8YFLogxK

U2 - 10.1111/php.12133

DO - 10.1111/php.12133

M3 - Article

C2 - 23834078

AN - SCOPUS:84887376105

VL - 89

SP - 1327

EP - 1334

JO - Photochemistry and Photobiology

JF - Photochemistry and Photobiology

SN - 0031-8655

IS - 6

ER -