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Abstract: Imprinting with macrocyclic nickel complexes having pendant functional groups, we have developed MIPs having much greater rebinding capacities than have previously been reported for supramolecular interactions. Three distinct supramolecular modes of polymer/metal complex binding have been explored singly and in pairs, hydrogen bonding, electrostatic attraction, and minor ligand binding. Two different kinds of binding sites were found for systems having both electrostatic and hydrogen bonding groups, with substrate affinities differing by 40-50x, with the weaker site binding 4x as strongly as MIPs based on hydrogen bonding alone. Under conditions that maintain polymer morphology, synergism between hydrogen bonding and electrostatic interactions (or minor ligand binding) enhanced rebinding by a factor as great as 20 over either affinity source alone. Best results were found with acetonitrile as the solvent during rebinding, but, surprisingly, performance was -90% as good using water as the solvent. Stereoisomers of the complexes showed both imprinting selectivity and an underlying intrinsic site affinity.