Aqueous suspensions of N,N-Dihexadecyl-l,2-ethanediarnine-N:N'-diacetic acid (1 d) give stable vesicles on sonication at pH = 3.5 and 9.0. The outer vesicle surface chelates copper(I1) and iron(lI1) ions without vesicle precipitation. Chelating micelles'.*) and vesicles are of interest because they allow the attachment of redox-active metal ions. If the aggregate also contains a photochemically active dye, e.g. a porphyrin, such systems may be used for light-induced charge separation3'. We report here on the synthesis and chelating properties of a vesicle with ethylenediaminediacetic acid head groups.The title compound Id was prepared from N-(2-aminoethyl)acetamide (1 a) by dialkylation with hexadecyl bromide in ethanol to give l b , removal of the acetyl protecting group in ethanolic sodium hydroxide and treatment of l c with chloroacetic acid in dirnethylformamide. The overall yield was 28 070.Ultrasonication of aqueous suspensions of 1 d gave stable, slightly opaque solutions at pH = 2 and 9. At pH = 6 the clear solution became turbid within a few hours.Electron micrographs of the evaporated solutions indicated the presence of vesicles with diameters ranging from 500-2000 A (Fig. 1). Water insoluble magnesium octaethylporphyrin could be dissolved t o a concentration of about molar in the vesicular solutions.
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