Multiarmed Macrocyclic Polyamines Exhibiting Unique Cation-Binding and Cation-Transport Properties toward Alkali-Metal and Alkaline-Earth Metal Cations

Article abstract of DOI:10.1021/jo00025a028

A variety of multiarmed macrocyclic polyamines were prepared as new type of metal carrier, which amide-, ester-, nitrile-, and ketone-functionalized arms were attached as secondary donor sites.Extraction and 13C NMR binding experiments revealed that their cation-binding behavior was largely dependent on the nature of the arm donor group as well as the size of the parent polyamine ring.In particular, introduction of an amide-functionalized arm into a suitable polyamine ring significantly enhanced binding ability toward "hard" metal cations, while the parent polyamine ring weakly bound these metal cations.Their unique cation-binding properties offered an effective membrane transport of hard metal cations.Since the cation-binding and -transport profiles of the new multiarmed macrocyclic polyamines differed greatly from those observed with conventional polyamines and related macrocycles, the present study provides a new possibility for designing a novel, macrocyclic polyamine type of synthetic carrier.