Boronic acid fluorophore/beta-cyclodextrin complex sensors for selective sugar recognition in water

Analytical Chemistry
A J TongN Teramae

Abstract

A novel boronic acid fluorophore 1/beta-cyclodextrin (beta-CyD) complex sensor for sugar recognition in water has been designed. The probe 1 bearing pyrene moiety as a fluorescent signal transducer exhibits no fluorescence emission, due to its aggregation in water containing 2% DMSO; however, the addition of beta-CyD to this solution largely changes UV-vis and fluorescence spectra of 1 by forming an inclusion complex with beta-CyD, and an efficient fluorescence emission response of 1/beta-CyD complex upon sugar binding is found to be obtained at pH 7.5. The pH-fluorescence profile of the 1/beta-CyD complex reveals that the boronate ester formation with fructose induces the apparent pKa shift from 7.95+/-0.03 in the absence of fructose to 6.06+/-0.03 in the presence of 30 mM fructose, resulting in the fluorescence emission response under the neutral condition. The spectral properties of 1 in 95% methanol:5% water (v/v), as well as the fluorescence quenching study of 1-methylpyrene with 4-methoxycarbonylphenyl-boronic acid 2, demonstrate that the response mechanism is based on the photoinduced electron transfer (PET) from the pyrene donor to the acid form of phenylboronic acid acceptor in 1, and thus, the proton dissociation of p...Continue Reading

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