The Dependence of the Polarity of Solvents on 1,3 : 2,4-Di-O-benzylidene-d-sorbitol Gel

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Abstract
1,3 : 2,4-Di-O-benzylidene-d-sorbitol (d-DBS) is known as a chiral oil gelator for a wide variety of organic solvents. The relationship between texture, structure of the gel, and the aggregated structure formed by d-DBS was investigated in various solvents. In the low polar solvents, the gel held a mesh type network structure in which the fiber appeared to be a rope-like helical structure. In the moderately polar solvents, the gel held an isotropic mesophase, but in the polar solvents, a spherulite texture was observed. From the experiments for the critical gel concentration of d-DBS in various solvents, it is assumed that there are three regions that differ in the form of hydrogen bonding, depending upon the polarity of solvents. By IR spectroscopic measurements, we found that, with the increase of solvent polarity, the hydrogen bonding between d-DBS and the solvent became more predominant than the intramolecular hydrogen bonding, and the hydrogen bonding between d-DBS became weaker at the same time. In addition, the intensities of CD spectra in the d-DBS gel decreased according to the increase of the solvent polarity. Here it is considered that textures and structurs observed in the gel are related to the aggregated structure that is mainly formed through hydrogen bonding among d-DBS.