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

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 beta-cyclodextrin (FPB-beta CyD) and an anthracene-based probe having a boronic acid moiety (1). Hydrophobic 1 is encapsulated in the cyclodextrin cavity of FPB-beta CyD, making the supramolecular complex (1/FPB-beta CyD) applicable in a water-rich solvent mixture (98% water). Interestingly, 1/FPB-beta CyD 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.