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

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 opto-electronic response to anions differs in solution and the films, with a distinct colorimetric response observed only in the film.