Boron effect on sugar‐based organogelators

The reaction of several alkylglucosides with phenyl boronic acid permitted an easy access to a series of alkylglucoside phenyl boronate derivatives. This type of compounds has structures similar to the known benzylidene glucoside organogelators except the presence of a boronate function in place of the acetal one. Low to very low concentrations of these amphiphilic molecules produced gelation of several organic solvents. The rheological properties of the corresponding soft materials characterized them as elastic solids. They were further characterized by SEM to obtain more information on their morphologies and by SAXS to determine the type of self-assembly involved within the gels. The sensitivity of the boronate function towards hydrolysis was also investigated. We demonstrated that a small amount of water (5% v/v) was sufficient to disrupt organogels leading to the original alkylglucoside and phenyl boronic acid; an important difference with the stable benzylidene-based organogelators. Such water sensitive boronated organogelators could be suitable substances for the preparation of smart soft material for topic drug delivery.