Synthesis, Self-association, and Anion Recognition of Conjugated Macrocycles Composed of Carbazole and Triazolium Moieties

Conjugated macrocycles 1·BF4 and 1·PF6 composed of carbazole and triazolium moieties were successfully synthesized. These macrocycles effectively self-associate through π–π stacking interactions in solution. They complex with halide ions in the cavity through C–H⋯X− hydrogen bonds, and intriguingly exhibit higher affinity for I− than for Cl− and Br−. The self-association and complexation ability with halide ions of macrocycles 1·BF4 and 1·PF6 are significantly enhanced compared to macrocycle 2 composed of carbazole and triazole moieties.