The Aggregated Higher-Structure of 1,3 : 2,4-Di-0-benzylidene-D-sorbitol in Organic Gels

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1,3 : 2,4-Di-<i>O</i>-benzylidene-<FONT SIZE="-2">D</FONT>-sorbitol (<FONT SIZE="-2">D</FONT>-DBS) can cause gelation of organic solvents of a wide range of polarity into a gel state. The aggregated structures of <FONT SIZE="-2">D</FONT>-DBS/organic solvent systems were studied, mainly by using IR, UV, and circular dichroism (CD) spectroscopy. In the case of the racemate <FONT SIZE="-2">DL</FONT>-DBS, no gel state was formed. In IR spectra of <FONT SIZE="-2">D</FONT>-DBS and <FONT SIZE="-2">DL</FONT>-DBS in the solid state, the intensities of <i>ν</i>OH and <i>ν</i>CO absorption in <FONT SIZE="-2">D</FONT>-DBS were found to be larger than those in <FONT SIZE="-2">DL</FONT>-DBS. It is assumed that the hydrogen bonding formed between an acetal oxygen and a hydroxyl group in the aggregation of <FONT SIZE="-2">D</FONT>-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 <FONT SIZE="-2">D</FONT>-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 <FONT SIZE="-2">D</FONT>-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 <FONT SIZE="-2">D</FONT>-DBS forms a helical structure of thin fibrous crystals in the gel state.

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  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(1), 146-151, 1995-01-15

    The Chemical Society of Japan

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各種コード

  • NII論文ID(NAID)
    10008884562
  • NII書誌ID(NCID)
    AA00580132
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    00092673
  • データ提供元
    CJP書誌  J-STAGE 
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