3-Hydroxybenzo[g]quinolones: dyes with red-shifted absorption and highly resolved dual emission.
Fiche publication
Date publication
août 2009
Auteurs
Membres identifiés du Cancéropôle Est :
Pr MELY Yves
Tous les auteurs :
Bilokin MD, Shvadchak VV, Yushchenko DA, Klymchenko AS, Duportail G, Mely Y, Pivovarenko VG
Lien Pubmed
Résumé
New derivatives of 3-hydroxyquinolone (3HQ) with a fused benzene ring (3-hydroxybenzo[g]quinolones) have been synthesized. They display a remarkable red shift of their absorption spectrum in comparison with other 3HQ analogs allowing their excitation by common He/Cd and Ar-ion lasers. As a result of their irreversible excited-state intramolecular proton transfer (ESIPT) reaction, they display a dual fluorescence in a series of solvents of varying polarities, starting from toluene to methanol. The dual emission of these dyes correlates well with solvent H-bond basicity, which is connected with the effect of this solvent property on the kinetics of the ESIPT reaction. In addition to their red-shifted absorption and fluorescence, these new derivatives show a larger separation of their two emission bands and a more appropriate range of their intensity ratio than the previously synthesized 3HQs. These properties allow an improved ratiometric evaluation of the local H-bond basicity of unknown environments, which will favor future applications of the new dyes in polymer and biological sciences. (C) 2009 Elsevier Ltd. All rights reserved.
Référence
Tetrahedron Lett. 2009 Aug 19;50(33):4714-9.