Harnessing solid-state packing for selective detection of chloride in a macrocyclic anionophore

Abstract

We report the synthesis of an inherently fluorescent macrocyclic receptor for chloride. The use of a disulphide tether provides for an excellent yield in the macrocyclization step. This compound binds chloride in the solution and solid state, and while unstable over time in aqueous solution, shows a selective response toward chloride over other anions in the solid state due to intermolecular interactions between fluorophore backbones. Surprisingly, the optoelectronic response to anions differs in solution and the films, with a distinct colorimetric response observed only in the film.