A Crown Ether Decorated Dibenzocoronene Tetracarboxdiimide Chromophore: Synthesis, Sensing, and Self-Organization

A macrocyclic dibenzocoronene tetracarboxdiimide containing two benzo-21-crown-7 groups has been synthesized. It shows liquid-crystalline behavior and selectively binds Pb2+ or K+ to form 1:2 complexes in solution. The complexation leads to a significant increase of fluorescence; the surface organization of discotic columnar structures, in the solid-state, can be controlled by selective ion binding.