Understanding the gelation properties of the fluorophenyl glycosides of arabinoside gelators: experimental and theoretical studies

Abstract

In supramolecular gelation, fluorinated gelators are important due to the unique properties displayed by these compounds that arise out of the presence of fluorine atoms. Generally, incorporation of fluorine leads to higher mechanical strength of the gels compared to their non-fluorinated counterparts and this property is enhanced with increasing the number of fluorine atoms. Herein, we show that the incorporation of fluorine into the phenyl ring of phenyl arabinoside allows the molecule to act as a gelator, unlike the non-fluorinated compound. We also show that the mechanical strength and stiffness of the gels is not only dependent on the positions of the fluorine atoms but also guided by their number. Detailed experimental studies, supported by computational studies, allowed us to rationalize the observed supramolecular interactions and propose reasons based on the conformational preferences of these compounds that allow additional hydrogen bonds and π–π interactions which guide the self-assembly, in addition to the primary H-bonding interactions. This, in turn, affects the mechanical behavior of these gels.