Sugar-poly(para-phenylene ethynylene) conjugates as sensory materials: efficient quenching by Hg2+ and Pb2+ ions

Three polar poly(para-phenylene ethynylene)s (PPE) were synthesized by utilizing the Heck-Sonogashira protocol. Two of the PPEs carry beta-glucopyranose substituents. Depending upon the linker used between the glycol units and the backbone, the fluorescence of these PPEs can be quenched by Hg2+ and Pb2+ to a varying degree. Monomeric model compounds that are substituted with only one glucose unit are not efficiently quenched. The presence of many glucose substituents in one PPE assembly led to a large increase in the binding constant to Hg2+ and quenching of the fluorescence was amplified.