NEW TETRAHETEROCYCLIC MACROCYCLES CONTAINING TRIAZOLE, PYRAZOLE, PYRIDINE, AND OR FURAN SUBUNITS - SYNTHESIS AND CATION BINDING-PROPERTIES

Ten new tetraheterocyclic macrocyclic ligands 2–4 in the porphyrinogen series were prepared. Their structures differ from 1 in (1) the type of junction between hetrocycles (NCH2C or CCH2C), (2) the donor nature of the complexation sites, (3) the five- or six-membered geometry of the included heterocycles, and (4) their symmetry. The capabilities of 2–4 for extraction and transport of alkali metal and NH4+ cations were less than those of 1. The rigid dipyrazole ditriazole macrocycles 3 extract Na+ selectively, whereas the more flexible dipyrazole monotriazole monopyridine macrocycles 2 have the best transport selectivity for Na+. © 1990, American Chemical Society. All rights reserved.