Perturbation of planarity as the possible mechanism of solvent-dependent variations of fluorescence quantum yield in 2-aryl-3-hydroxychromones.

Autor: Klymchenko AS; Research Institute for Genetic Engineering and Biotechnology, TUBITAK Marmara Research Center, Gebze-Kocaeli 41470, Turkey., Pivovarenko VG, Demchenko AP
Jazyk: angličtina
Zdroj: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy [Spectrochim Acta A Mol Biomol Spectrosc] 2003 Mar 01; Vol. 59 (4), pp. 787-92.
DOI: 10.1016/s1386-1425(02)00233-0
Abstrakt: In order to understand the unexpectedly low quantum yields of 3-hydroxyflavones (3-HFs) in certain solvents, such as acetonitrile or ethyl acetate, the comparative study of solvent-dependent properties of parent 3-HF, 2-furyl-3-hydroxychromone and 2-benzofuryl-3-hydroxychromone derivatives have been performed. The results suggest that the formation of intermolecular hydrogen bond of 3-hydroxy group with the solvent favors non-planar conformations of phenyl group with respect to chromone system. This steric hindrance is not observed in the case of furan- and benzofuran-substituted 3-hydroxychromones (3-HCs). These results suggesting a new strategy for dramatic improvement of fluorescence properties of 3-HCs as two-wavelength ratiometric fluorescence probes.
Databáze: MEDLINE