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

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Abstract

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.

Journal

  • 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

References:  25

  • <no title>

    HONMA M.

    Gendaikagaku 197, 54, 1987

    Cited by (3)

  • <no title>

    TACHIBANA T.

    Bull. Chem. Soc. Jpn. 52, 34, 1979

    Cited by (10)

  • <no title>

    TACHIBANA T.

    J. Am. Chem. Soc. 42, 3422, 1969

    Cited by (1)

  • <no title>

    TACHIBANA T.

    Bull. Chem. Soc. Jpn. 45, 415, 1974

    Cited by (1)

  • <no title>

    TACHIBANA T.

    Bull. Chem. Soc. Jpn. 43, 2418, 1970

    Cited by (6)

  • <no title>

    LIN Y.-C.

    J. Am. Chem. Soc. 111, 5542, 1989

    Cited by (15)

  • <no title>

    NAKASHIMA N.

    J. Am. Chem. Soc. 107, 509, 1985

    Cited by (25)

  • <no title>

    PFANNEMULLER B.

    Chem. Phys. Lipids 37, 227, 1985

    Cited by (1)

  • <no title>

    FUHRHOP J. -H.

    J. Am. Chem. Soc. 109, 3387, 1987

    Cited by (11)

  • <no title>

    FUHROP J. -H.

    J. Am. Chem. Soc. 112, 1768, 1990

    Cited by (1)

  • <no title>

    YANAGAWA H.

    J. Am. Chem. Soc. 111, 4567, 1989

    Cited by (10)

  • <no title>

    ANDERMAN D.

    J. Am. Chem. Soc. 111, 6536, 1989

    Cited by (1)

  • <no title>

    LIN Y-C.

    Macromolecules. 20, 414, 1987

    Cited by (5)

  • <no title>

    NAKAMOTO K.

    J.Am.Chem.Soc. 77, 6480, 1955

    Cited by (7)

  • <no title>

    TINOCO I.

    J. Am. Chem. Soc. 82, 4785, 1960

    Cited by (3)

  • <no title>

    KUNITAKE T.

    J. Am. Chem. Soc. 102, 6642, 1980

    Cited by (8)

  • <no title>

    KUNITAKE T.

    J. Chem. Soc. Chem. Commun. 1986, 655

    Cited by (5)

  • <no title>

    WILSON E. B.

    Molecular Vibration, 1955

    Cited by (2)

  • <no title>

    HASS C.

    J. Chem. Phys. 32, 1763, 1959

    Cited by (1)

  • <no title>

    MIYAZAWA T.

    Spectrochim. Acta 16, 1231, 1960

    Cited by (1)

  • <no title>

    MIYAZAWA T.

    J. Chem. Phys. 35, 693, 1961

    Cited by (1)

  • <no title>

    GREEN J. L.

    J. Phys. Chem. 90, 3958, 1986

    Cited by (2)

  • <no title>

    YAMAMOTO S.

    Kougyou Kagaku Zasshi 45, 695, 1942

    Cited by (4)

  • <no title>

    PLATT J. R.

    J. Chem. Phys. 17, 484, 1949

    Cited by (3)

  • <no title>

    PHILPOTT M.

    J. Chem. Phys. 57, 2026, 1972

    DOI  Cited by (1)

Codes

  • NII Article ID (NAID)
    10008884562
  • NII NACSIS-CAT ID (NCID)
    AA00580132
  • Text Lang
    ENG
  • Article Type
    ART
  • ISSN
    00092673
  • Data Source
    CJP  J-STAGE 
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