Alkylboronate -Phenylglucoside versus Phenylboronate -Alkylglucoside Organogelators

Low molecular weight organogelators provide useful materials which have already found applications in various fields. Recently, phenylboronate alkylglucosides have become new members of this type of organogelators providing water-sensitive gels. This work is focused on the impact of the position of alkyl and phenyl moieties within this type of structures. Thus, alkylboronate phenylglucoside and alkylboronate alkylglucoside counterparts were synthesized and studied. Organogels obtained in toluene and ethyl myristate were characterized by rheology and electron microscopy. In addition, we also determined the disruption rates of such organogels upon addition of a small amount of water. Alkylboronate alkylglucosides did not induce gelation of the tested solvents but all derivatives bearing a phenyl ring either on the boronate function or on the glucoside unit came out as good organogelators. However, alkylboronates were found to have higher water sensitivities than phenyl counterparts. Thus, this work has enlarged the scope of glucoside-boronate organogelators and their water sensitivity which can represent useful materials in drug delivery systems for example.