Synthesis and Self-Assembly of Cyclic 2,7-Anthrylene Ethynylene 1,3-Phenylene Ethynylene Trimer with a Planar Conformation.

Cyclic arylene ethynylene hexamer 1, composed of alternating 2,7-anthrylene ethynylene units and meta-phenylene ethynylene units, was synthesized. It shows C symmetry and possesses a flat and rigid conformation with a large equilateral triangle-like cavity. Macrocycle 1 self-associates through π-π stacking interactions between the anthracene-containing macrocyclic aromatic cores with indefinite-association constant K =6980 m in CDCl at 303 K. Macrocycle 1 also self-assembles into π-stacked nanofibers in the drop-cast film.