Computational Study on the Anomalous Fluorescence Behavior of Isoflavones

被引：18

作者：

Beyhan, S. Maya ^{[1
]}

Gotz, Andreas W. ^{[1
]}

Ariese, Freek ^{[2
]}

Visscher, Lucas ^{[1
]}

Gooijer, Cees ^{[2
]}

机构：

[1] Vrije Univ Amsterdam, ACMM, NL-1081 HV Amsterdam, Netherlands

[2] Vrije Univ Amsterdam, LaserLAB, NL-1081 HV Amsterdam, Netherlands

来源：

JOURNAL OF PHYSICAL CHEMISTRY A | 2011年 / 115卷 / 09期

关键词：

STATE PROTON-TRANSFER; DENSITY-FUNCTIONAL THEORY; GAUSSIAN-BASIS SETS; EXCITED-STATES; LUMINESCENCE BEHAVIOR; 1ST-ORDER PROPERTIES; EXCITATION-ENERGIES; DIETARY FLAVONOIDS; 7-HYDROXYFLAVONE; 3-HYDROXYFLAVONE;

D O I：

10.1021/jp109059e

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Isoflavones are known to show fluorescence with intensities that depend strongly on the solvent properties and exhibit Stokes' shifts as large as 1.4 eV. While some of this behavior can be explained by (excited state) deprotonation, this mechanism does not: apply for all isoflavones. The aim of this study is to computationally and experimentally investigate the reasons for this anomalous behavior of neutral isoflavones, taking the daidzein molecule as a model compound. We find that the absence in fluorescence in aprotic solvents and the weak fluorescence in protic solvents can be explained by a change of order of the lowest singlet states in which a fluorescent charge-transfer state lies below the. nonfluorescent locally excited state in water but not in acetonitrile. The large Stokes' shift is partly due to a significant rotation among the chromone-phenyl bond in the excited, state.

引用

页码：1493 / 1499

页数：7

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