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.

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► New LMOG’s based on glucose.
► Enhancement of gelation capability by secondary effects.
► Gelation of unconventional organic solvents (DMSO, methanol, propanol).