Neutral heteroditopic [2]rotaxane ion-pair host systems were synthesised via a Cu(ii) directed passive metal template strategy. Each rotaxane contains discrete, axle-separated interlocked binding sites for a guest anion and a transition metal countercation. The anion binding sites are composed of convergent X-H (X = C, N) hydrogen bond donor groups, or mixed X-H and C-I hydrogen and halogen bond donor groups, whereas an equivalent three-dimensional array of amine, pyridine and carbonyl oxygen donor groups comprise the transition metal binding site. H NMR titrations experiments in CDCl/CDOD or CDCl/CDOD/DO solvent mixtures reveal that the heteroditopic [2]rotaxane host systems are capable of cooperative anion recognition in the presence of a co-bound Zn(ii) cation.
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