The present invention provides halogenated calixpyrrole, calixpyridinopyrrole, and calixpyridine macrocycles having 4–12 pyrrolic rings with greater stability, enhanced anion and neutral molecule binding affinity, and different binding selectivites as compared to their non-halogenated congeners as judged from 1H NMR, 19F NMR and fluorescence emission spectroscopic analyses.