A Pb2+-binding polychelatogen derived from thionated lactide

Abstract

The synthesis and characterization of a polychelatogen derived from thionated lactide is reported. The four step synthesis from L-LA requires thionation and thia-Diels–Alder steps to afford a highly strained spiro-lactone adduct that is amenable to ring-opening metathesis polymerization. Saponification of the polymer affords a polyanion that exhibits a high affinity for toxic Pb²⁺ in aqueous solutions, results that we attribute to thioether and hydroxy carboxylate chelating moieties that are integrated into the polymer backbone and residues respectively.