Substituent Effects on Monoboronic Acid Sensors for Saccharides Based on N-Phenyl-1,8-naphthalenedicarboximides

Haishi Cao, Tom McGill, Michael D. Heagy

Research output: Contribution to journalArticlepeer-review

61 Scopus citations

Abstract

In the course of our investigations on new monoboronic acid saccharide sensors with C0 spacers, a series of probes 1-6 based on 1,8-naphthalenedicarboximide were synthesized. Sensor 1 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 (φF = 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.

Original languageEnglish (US)
Pages (from-to)2959-2966
Number of pages8
JournalJournal of Organic Chemistry
Volume69
Issue number9
DOIs
StatePublished - Apr 30 2004
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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