Synthetic Receptors with Micromolar Affinity for Chloride in Water.

Abstract

A water-soluble coordination cage was obtained by reaction of Pd(NO3 )2 with a 1,3-di(pyridin-3-yl)benzene ligand featuring a short PEG chain. The cavity of the metal-organic cage contains one nitrate anion, which is readily replaced by chloride. The apparent association constant for chloride binding in buffered aqueous solution is Ka =1.8(±0.1)×105 M-1 . This value is significantly higher than what has been reported for other macrocyclic chloride receptors. The heavier halides Br- and I- compete with binding or self-assembly, but the receptor displays very good selectivity over common anions such as phosphate, acetate, carbonate, and sulfate. A further increase of the chloride binding affinity by a factor of 3 was achieved using a fluorinated dipyridyl ligand.