The present invention provides calixpyrrole, calixpyridinopyrrole, and
calixpyridine macrocycles, having 4, 5, 6, 7, or 8 heterocyclic rings, as
well as syntheses, derivatives, conjugates, multimers, and solid supports
thereof. Such macrocycles have proved to be effective and selective ion-
and neutral molecule-binding agents forming supramolecular ensembles, and
ion- and neutral molecule-separation agents. The macrocycles are fully
meso-non-hydrogen-substituted porphyrinogens, a few molecules of which
were previously known but not recognized as possessing anion- or
molecule-binding properties. The binding mode is noncovalent, primarily
that of hydrogen-bonding, thereby providing a new mode for liquid
chromatography, that of Hydrogen Bonding Liquid Chromatography. Further
useful applications of the macrocycles provided herein include
environmental remediation by removal of undesired ions or neutral
molecules, and removal of phosphate for kidney dialysis.