Synthesis and Vesicle-forming Ability of the Amphiphilic Compound Composed of a Single Lipophilic Chain and a Crown Ether Ring as a Hydrophilic Moiety

  • IKEDA Isao
    Department of Applied Chemistry, Faculty of Engineering, Osaka University;
  • TSUJI Takayuki
    Department of Applied Chemistry, Faculty of Engineering, Osaka University;
  • TANAKA Keiko
    Osaka Municipal Technical Research Institute;
  • TAKEDA Tokuji
    Osaka Municipal Technical Research Institute;
  • KUROSAWA Hideo
    Department of Applied Chemistry, Faculty of Engineering, Osaka University;
  • OKAHARA Mitsuo
    Department of Applied Chemistry, Faculty of Engineering, Osaka University;

Bibliographic Information

Other Title
  • クラウンエーテル環を親水基とする-鎖疎水基型両親媒性化合物の合成とべシクル形成能
  • Special articles on synthesis and supramolecular structure of functionality amphiphiles. Synthesis and vesicle-forming ability of the amphiphilic compound composed of a single lipophilic chain and a crown ether ring as a hydrophilic moiety.

Description

In order to construct the bilayer membrane which has the ability of cation selectivity, amphiphilic compounds 1, 2 composed of a single lipophilic chain containing a rigid biphenylylene moiety and a 15-crown-5 or 18-crown-6 ether ring as a hydrophilic moiety were synthesized. In the presence of potassium cation, especially potassium acetate, 18-crown-6derivatives 2a, b dispersed transparently and stably in water by sonication. The presence of particles including water phase in this solution was demonstrated by the entrapment of aqueous solution of carboxyfluorescein as a fluorescence probe. The size of particles, amounting more than 90-'98% in weight, measured by a light-scattering method was in the range of 120-380A. This size was affected a little by the size of lipophilic group. Different from vesicles formed with ionic compound, those formed with 2 could be destroyed by heating to release the inner aqueous solutions. Influence of fatty acid salts on the structure of the bilayer membrane was examined. And it was disclosed that potassium oleate stabilized the dispersing system markedly, and the volume of inner aqueous phase of the vesicle was affected.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1990 (10), 1059-1064, 1990-10-10

    The Chemical Society of Japan

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