Substituent effects on monoboronic acid sensors for saccharides based on N-phenyl-1,8-naphthalenedicarboximides

被引：57

作者：

Cao, H ^{[1
]}

McGill, T ^{[1
]}

Heagy, MD ^{[1
]}

机构：

[1] New Mexico Inst Min & Technol, Dept Chem, Socorro, NM 87801 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 09期

关键词：

D O I：

10.1021/jo035760h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the course of our investigations on new monoboronic acid saccharide sensors with C-0 spacers, a series of probes 1-6 based on 1,8-naphthalenedicarboximide were synthesized. Sensor I displays features typical of PET monoboronic acid sensors and shows high selectivity to fructose. Sensor 2 exhibits a novel dual emission and remarkable sensitivity for glucose relative to fructose and galactose through subtle changes in pH. Sensor 3 displays significantly enhanced fluorescence in the presence of galactose at low pH. Although probes 4-6 exhibit unique properties such as high quantum yield (Phi(F) = 0.407) and excellent solubility in water, they did not show significant change in fluorescence intensity in the presence of monosaccharides. The effects of substituent on all six probes lend support to the proposed photoelectrochemical model.

引用

页码：2959 / 2966

页数：8

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