Conjugated macrocycles 1 center dot BF4 and 1 center dot PF6 composed of carbazole and triazolium moieties were successfully synthesized. These macrocycles effectively self-associate through pi-pi stacking interactions in solution. They complex with halide ions in the cavity through C-H center dot center dot center dot 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 macro cycles 1 center dot BF4 and 1 center dot PF6 are significantly enhanced compared to macrocycle 2 composed of carbazole and triazole moieties.