title: Fluorescence behavior of (selected) flavonols: a combined experimental and computational study.
abstract: In this article, results of (time-dependent) density functional theory (DFT and TDDFT) calculations are combined with experimental absorption and fluorescence measurements to explain fluorescence properties of a series of flavonols. The well-understood fluorescence properties of 3- and 5-hydroxyflavone are revisited and validate our combined experimental and theoretical approach. The accuracy of the computational data (energy differences for selected points at the PES, excitation energies and oscillator strengths) allows us to understand quite different experimentally observed fluorescence spectra in the presence of only subtle structural differences. We show that for flavonols with additional hydroxyl groups not the neutral molecule but rather anions lead to fluorescence and that solvation molecules need to be included explicitly in the theoretical calculations to obtain a sufficient accuracy-enabling the understanding and prediction of experimental data for flavonols belonging to different sub-classes.
authors.affiliation: Amsterdam Center for Multiscale Modelling (ACMM), Section Theoretical Chemistry, VU University Amsterdam, Amsterdam, The Netherlands. s.hoefener.@vu.nl
authors.forename: Sebastian
authors.initials: S
authors.lastname: Höfener
authors.forename: Pieter C
authors.initials: PC
authors.lastname: Kooijman
authors.forename: Janneke
authors.initials: J
authors.lastname: Groen
authors.forename: Freek
authors.initials: F
authors.lastname: Ariese
authors.forename: Lucas
authors.initials: L
authors.lastname: Visscher
mesh_terms: D047310:Apigenin / Q000737:chemistry; D005419:Flavonoids / Q000737:chemistry*; D044948:Flavonols; D006863:Hydrogen-Ion Concentration; D044949:Kaempferols / Q000737:chemistry; D008958:Models, Molecular; D011789:Quantum Theory; D011794:Quercetin / Q000737:chemistry; D013053:Spectrophotometry; D047309:Flavones
chemical_list: D047310:Apigenin; D005419:Flavonoids; D044948:Flavonols; D044949:Kaempferols; D011794:Quercetin; C062711:5-hydroxyflavone; C006552:kaempferol; C008548:morin; D047309:Flavones; C017875:fisetin; C041477:3-hydroxyflavone