Further evidence for the gelation ability–structure correlation in sugar-based gelators

Abstract

Eight methyl glycosides of 4,6- O-benzylidene derivatives of the monosaccharides d-glucose, d-mannose, d-allose and d-altrose were synthesized to systematically study the effect of small configurational changes on the ability to gelate organic solvents. Among the β anomers, only the d-mannose glycoside exhibits a strong gelation ability, whereas in the α-series the d-glucose and d-mannose derivatives act as versatile gelators. Also, as a general rule we found that the β anomers possess a higher ability to gelate solvents than the α anomers. The gelation properties are discussed on the basis of SAXS, FTIR, differential scanning calorimetric (DSC) measurements and scanning electron microscopy (SEM) observations. The temperature-dependent SAXS measurements were carried out to elucidate the sol–gel transition temperature. The present study emphasizes that the saccharide family provides, not only valuable information of the structural requirements for the design of new gelators, but also for molecular assembly systems in general.