Synthesis and ion binding properties of Rebek's cleft-type ionophores bearing two convergent carboxylic acid functions

Abstract

A series of new ligands having convergent dicarboxylic acid functions, based-upon Rebek's cleft-type ionophore, have been prepared and their ion binding properties were investigated by the competitive extraction and transport experiments. The main purpose of the modification was to increase the lipophilicity of the Rebek's ionophore, which was attempted by utilizing propyl analog of Kemp's triacid or by changing the bridging unit. Ionophores 5 and 6 were found to have a pronounced ion-binding property toward Ca2+ ion. The selectivity in competitive extraction of ionophore 5 at pH 9 for Ca2+ over Mg2+ and Sr2+ is 2.0 and 59.3, respectively. The selectivity in competitive transport of ionophore 5 for Ca2+ over Mg2+ and Sr2+ is 29.8 and 99.3, and that of ionophore 6 is 10.0 and 23.2, respectively.