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Bis crown ether molecules containing separate S and O donor sets are synthesized in two steps from commercially available benzocrown ethers. Double bromomethylation of the aromatic ring followed by S-C bond formation in a Cs+ mediated cyclization reaction produces ditopic macrocycles containing crown thioether and crown ether binding sites separated by a common benzene ring. These potential ligands display haptoselectivity, simultaneously coordinating a transition metal ion (Cu+) through S-donors and an alkali metal ion (Na+, K+) in the O-donor set. X-ray crystallographic and MR data verify the nature of the cation binding selectivity. The resulting complexes demonstrate the potential to bind a substrate molecule (AMP) between the two metal centres (Cu+ and Na+).
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