Tuning methyl 4,6-O-benzylidene α-d-glucopyranosides’ gelation ability by minor group modifications

Ten methyl 4,6-O-benzylidene α-d-glucopyranosides were synthesized for the purpose of studying systematically the effect of small group changes at position 4 of the aromatic ring on the ability to gelate organic solvents. The gelation properties are discussed on the basis of small angle X-ray scattering (SAXS), Fourier transform infrared spectroscopy (FTIR), differential scanning calorimetry (DSC) measurements, and scanning electron microscopy (SEM) observations. Sol–gel transition temperatures were determined simultaneously by DSC and temperature-dependent FTIR measurements. The current study emphasizes that carbohydrates furnish not only valuable information about structural requirements for organogelator design, but also for molecular assembly systems in general.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► New LMOG’s based on glucose. ► Enhancement of gelation capability by secondary effects. ► Gelation of unconventional organic solvents (DMSO, methanol, propanol).