A simple supramolecular complex of boronic acid-appended β-cyclodextrin and a fluorescent boronic acid-based probe with excellent selectivity for d-glucose in water

Abstract

Various diboronic acid-based chemosensors for d-glucose have been developed for use in diabetes diagnostic systems. However, most of these chemosensors have limitations, such as poor water solubility, difficulties in synthesis, and inability to selectively detect d-glucose from among other saccharides. We report a simple chemosensor based on a supramolecular complex of fluorophenylboronic acid-appended β-cyclodextrin (FPB-βCyD) and an anthracene-based probe having a boronic acid moiety (1). Hydrophobic 1 is encapsulated in the cyclodextrin cavity of FPB-βCyD, making the supramolecular complex (1/FPB-βCyD) applicable in a water-rich solvent mixture (98% water). Interestingly, 1/FPB-βCyD showed a strong turn-on response to d-glucose with a 9.6-fold enhancement in fluorescence intensity, and no response to other saccharides. This study uncovers an innovative approach based on the supramolecular assembly of simple components for the development of a water-soluble d-glucose chemosensor with excellent selectivity.