Mechanochemical click reaction as a tool for making carbohydrate-based triazole-linked self-assembling materials (CTSAMs)

•Lipophilic polyvalent click-glycosides were made by solvent-free mechanochemical reaction.•They self-assemble in long chain hydrocarbon solvents to form supramolecular structures.•TEM observations were rationalized computationally by geometry optimization.•One compound showed phase-selective gelation ability in a biphasic mixture of hexane and water.•Some of the compounds were moderately antimicrobial.

Various glycosides in which glycosylated triazole residues are anchored on to a central phenyl ring have been prepared under green reaction conditions by a solvent-free mechanochemical method. Some of the glycosides exhibited the ability to form gels when in contact with long chain hydrocarbons, e.g. hexane, heptane and octane, and this property was phase-selective. Thus, from a mixture of hexane–water, the compounds preferably absorbed the alkane to form a gel. The gelation ability was found to increase with an increasing number of substituents on the phenyl ring but only up to tetra-substitution. The hexa-substituted phenyl derivative did not swell in the hydrocarbon solvents investigated. The spontaneous self-assembling properties of these compounds in hexane have been investigated by transmission electron microscopy (TEM). Molecular modelling was used to optimize the structural geometry of these carbohydrate-based triazole-linked self-assembling materials (CTSAMs) and to rationalize their behaviour.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide