The Aggregated Higher-Structure of 1,3 : 2,4-Di-<i>O</i>-benzylidene-<scp>d</scp>-sorbitol in Organic Gels

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  • Seiji Yamasaki
    Tokyo Research Laboratories, Kao Corporation2-1-3 Bunka, Sumida-ku, Tokyo 131
  • Yukihiro Ohashi
    Tochigi Research Laboratories, Kao Corporation2606 Akabane, Ichikai-machi, Haga-gun, Tochigi 321-34
  • Hisao Tsutsumi
    Tokyo Research Laboratories, Kao Corporation2-1-3 Bunka, Sumida-ku, Tokyo 131
  • Kaoru Tsujii
    Kao Institute for Fundamental Research, Kao Corporation2606 Akabane, Ichikai-machi, Haga-gun, Tochigi 321-34

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Abstract

<jats:title>Abstract</jats:title> <jats:p>1,3 : 2,4-Di-O-benzylidene-d-sorbitol (d-DBS) can cause gelation of organic solvents of a wide range of polarity into a gel state. The aggregated structures of d-DBS/organic solvent systems were studied, mainly by using IR, UV, and circular dichroism (CD) spectroscopy. In the case of the racemate Dl-DBS, no gel state was formed. In IR spectra of d-DBS and Dl-DBS in the solid state, the intensities of νOH and νCO absorption in d-DBS were found to be larger than those in Dl-DBS. It is assumed that the hydrogen bonding formed between an acetal oxygen and a hydroxyl group in the aggregation of d-DBS. From the changes in the IR spectra from solution into a gel state, we can conclude that the chirality and the hydrogen bonding of DBS molecules are essential for the formation of the gel. Comparing the gel-forming ability of d-DBS with its derivatives, 5- or 6-hydroxyl-group-blocked compounds by methyl group, the 6-hydroxyl group seems to be important in the formation of d-DBS aggregates. The results of UV spectra suggest that the benzene rings are ordered in a side by side arrangement. The molar ellipticities in CD spectra increased about 500 times during the change from the solution to the gel state. From these results, it is concluded that d-DBS forms a helical structure of thin fibrous crystals in the gel state.</jats:p>

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