Amphiphilic alkyl (dodecyl and hexadecyl)-2-hydroxy-3-chloropropyl phosphates (C 12 - and C 16 -AHCP) were synthesized, and then alkyl glycidyl phosphates (C 12 - and C 16 -AGP) were quantitatively obtained by the treatment of AHCP with NaOH in order to prepare a novel vesicle which has reactive and polymerizable epoxy group on its membrane surface. The bilayer vesicles were formed by ultrasonication of aqueous dispersion of C 16 -AHCP or C 16 -AGP, but the vesicles composed of C 12 -AHCP and C 12 -AGP were not obtained by the same treatment. Both of C 16 -AHCP and C 16 -AGP bilayer vesicles are only stable at pH 5—10 or the ionic strength below 0.15. The gel-filtration chromatography and the UV-Vis absorption spectroscopic studies on Co(Ⅱ) tetrakis(propyloxycarbonyl)phthalocyanine as a lipophilic probe indicated that the phthalocyanine was effectively incorporated into the C 16 -AHCP bilayer membranes and predominantly present in a monomeric state in the membranes, which is much different from its leading diameric state in SDS micelle and ethanol.
The oxidation of thiophenol（RSH） to phenyl disulfide catalyzed by Co（Ⅱ） tetrakis（propyl-oxycarbonyl）phthalocyanine[CoPc（COOC3H7）4] in the presence of molecular oxygen was studied in synthetic bilayer membrane of vesicle, which is composed of hexadecyl 2-hydroxy-3-chloropropyl phosphate, SDS micelle, ethanol and benzene respectively. The catalytic activities followed the order of \{CoPc（COOC\}3H7）4 in the bilayer membrane>ethanol>benzene, and in the bilayer membraneSDS micelle. UV-Vis spectroscopic studies reveal that the catalytic oxidation proceeds through RS--CoPc-O2 intermediate. The catalytic activity of CoPc（COOC3H7）4 in the bilayer membrane of vesicle higher than that in the other media is considered to be attributable to the disaggregation of CoPc（COOC3H7）4 incorporated into the bilayer membrane and the easier H+ dissociation of RSH on the polar surface of the bilayer membrane bordered by bulk aqueous phase.
