Excited-state intramolecular proton transfer in 2-(2′,6′-dihydroxyphenyl) benzoxazole: effect of dual hydrogen bonding on the optical properties

被引：64

作者：

Chen, Wei-Hua

Pang, Yi ^{[1
]}

机构：

[1] Univ Akron, Dept Chem, Akron, OH 44325 USA

来源：

TETRAHEDRON LETTERS | 2010年 / 51卷 / 14期

基金：

美国国家科学基金会;

关键词：

2-(2; 6; '-Dihydroxyphenyl)benzoxazole; Excited-state intramolecular proton transfer; Hydrogen bonding; Rotamer; Fluorescence; SENSOR; 2-(2'-HYDROXYPHENYL)BENZOXAZOLE; FLUORESCENCE; DERIVATIVES; ROTAMERISM;

D O I：

10.1016/j.tetlet.2010.02.043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-(2',6'-Dihydroxyphenyl)benzoxazole (DHBO) has been synthesized by using palladium-catalyzed oxidative cyclization. The compound Utilizes both O-H center dot center dot center dot N and O-H center dot center dot center dot O bonds to ensure a coplanar structure between the benzoxazole and phenol fragments. Optical Comparison with the parent compound 2-(2'-hydroxyphenyl)benzoxazole (HBO) reveals that the dual hydrogen bonding in DHBO plays an essential role in raising the desirable keto emission for ESIPT and tuning the polarity sensitivity toward the molecular environment. DHBO also exhibits a higher quantum yield (phi(fl) = 0.108 in methanol) than HBO (phi(fl) = 0.0025) in the same solvent. (C) 2010 Elsevier Ltd. All rights reserved.

引用

页码：1914 / 1918

页数：5

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