Cyclic arylene ethynylene hexamer 1, composed of alternating 2,7-anthrylene ethynylene units and meta-phenylene ethynylene units, was synthesized. It shows C3 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 KE=6980 m−1 in CDCl3 at 303 K. Macrocycle 1 also self-assembles into π-stacked nanofibers in the drop-cast film.
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