Calixpyrroles, calixpyridinopyrroles and calixpyridines

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Date

2001-07-17

Authors

Jonathan L. Sessler
Vladimir A. Kral
Petra I. Sansom
Andrei Andrievsky
William E. Allen
Philip A. Gale
Andreas Gebauer
John W. Genge
Vincent Lynch
Christopher T. Brown

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United States Patent and Trademark Office

Abstract

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.

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