Titre du document / Document title

On the Inoperativeness of the ESIPT Process in the Emission of 1-Hydroxy-2-acetonaphthone : A Reappraisal

Auteur(s) / Author(s)

CATALAN J. ; DE PAZ J. L. G. ;

Résumé / Abstract

For a molecule which contains an intramolecular hydrogen bond (IMHB) in its chemical structure to undergo an excited singlet intramolecular proton transfer (ESIPT) process, on photoexcitation, there must occur a simultaneous increase, in a substantial manner, in the acidity of the proton donor and the basicity of the proton acceptor forming the IMHB [J. Am. Chem. Soc. 2001, 123, 11940]. For the reason that those changes occur on photoexcitation of the 2-hydroxyacetophenone but not for 1-hydroxy-acetonaphthone, one draws the conclusion that, while ESIPT is operative in the 1(π,π*)¹ electronic state of the monocyclic compound 2-hydroxyacetophenone, it is not operative in its bicyclic homolog 1-hydroxy-2-acetonaphthone. We have shown the photophysics of 1-hydroxy-2-acetonaphthone in its first excited electronic state to be governed by two stable, easily reconverted enol structures, the presence of which causes the peaks in the free-jet fluorescence excitation spectrum for the compound to split into two of similar strength. In this paper, we rationalize photophysical evidence for 1-hydroxy-2-acetonaphthone obtained by femtosecond spectroscopy over the past 13 years in the light of existing photophysical patterns based on steady-state spectra for the compound [J. Am. Chem. Soc. 1993, 115, 4321].

Revue / Journal Title

The journal of physical chemistry. A   ISSN 1089-5639 

Source / Source

2008, vol. 112, n^o5, pp. 904-914 [11 page(s) (article)]

Langue / Language

Anglais

Editeur / Publisher

American Chemical Society, Washington, DC, ETATS-UNIS  (1997) (Revue)

Localisation / Location

INIST-CNRS, Cote INIST : 549 A, 35400018347352.0180