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    Revisiting a '3 + 1' convergent stepwise strategy permitted the synthesis of [14]imidazoliophane in excellent yield for a macrocyclization. The new [14]triazoliophane and bis(1,2,3-triazolium) counterpart were less synthetically accessible and the hybrid derivative proved troublesome to prepare. Triazolophane was devoid of anion-binding affinities, while charged [14]heterophane prototypes showed a particular preference for acetate. When association constants were compared, dicationic systems and showed greater values than monocationic macrocycle , and the highest affinities corresponded to the bis(imidazolium) receptor .


    Neus Mesquida, Immaculada Dinarès, Anna Ibáñez, Ermitas Alcalde. 14]Heterophane prototypes containing azolium and/or azole anion-binding motifs. Organic & biomolecular chemistry. 2013 Oct 7;11(37):6385-96

    PMID: 23959333

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