A supramolecular gel based on a glycosylated amino acid derivative with the properties of gel to crystal transition

Abstract

Here we report the generation of a novel gelator from a glycosylated amino acid derivative, which contained three structural units, an aromatic residue, a carbohydrate moiety and a tert-butyl group in a single molecule. These structural units can promote the supramolecular self-assembly of this gelator in both aprotic and protic solvents via coordinated pi-pi stacking, multiple hydrogen binding and van der Waals interactions. More importantly, due to their non-equilibrium natures, the organogels formed in DCM, chloroform and ethanol can undergo gel to crystal transition in storage, driven by unbalanced gelator-gelator and solvent-gelator interactions. In this process, the gelators were firstly trapped in a kinetically favorable gel state, and then transferred into a more thermodynamically stable crystal state upon ageing, with the generation of microcrystals in different morphologies.