TOWARD THE PHOTOSTABILITY MECHANISM OF INTRAMOLECULAR HYDROGEN-BOND SYSTEMS - THE PHOTOPHYSICS OF 1'-HYDROXY-2'-ACETONAPHTHONE

被引:113
|
作者
CATALAN, J
DELVALLE, JC
机构
[1] Departamento de Química Fisica Aplicada, Universidad Autónoma de Madrid, E-28049 Madrid, Cantoblanco
关键词
D O I
10.1021/ja00063a057
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The photophysical behavior of 1'-hydroxy-2'-acetonaphthone in dry cyclohexane, methanol, and dimethyl sulfoxide was studied. The compound was found to exhibit a single fluorescence band (both at room temperature and at 77 K) that was scarcely dependent on the solvent used as well as an anomalously small Stokes shift (ca. 6000 cm-1) for an excited-state intramolecular proton-transfer mechanism and a fluorescence spectrum similar to the mirror image of its absorption spectrum. The compound was also found to exhibit a single fluorescence band both in gas phase at 368 K and in crystal phase at 298 K. Despite the fact that the compound seemingly undergoes a proton phototransfer, it is no more photostable than 2-(2'-hydroxy-5'-methylphenyl)benzotriazole itself, which is regarded as the archetype of photostability. This finding sheds some light on the mechanism whereby substances containing an intramolecular hydrogen bond acquire their photostability.
引用
收藏
页码:4321 / 4325
页数:5
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