Catenaries and rotaxanes are highly attractive synthetic targets in supramolecular chemistry due, in part, to their potential uses as molecular machines or as selective hosts for ionic and molecular guests. The preparation of higher-order interlocked architectures provides a much greater synthetic challenge than the construction of the prototypical 2catenanes and 2rotaxanes, but can allow for functionality not open to simpler systems. Indeed, impressive examples of such species have been assembled using cationic and neutral templates. In contrast, the use of anion templation to generate interlocked structures, whilst having been demonstrated by us and others, remains in its infancy. In particular, almost all reports of anion templation of interlocked molecules involve the construction of either 2catenane or 2rotaxane structures. A "handcuff" catenane is an example of a higher-order interlocked architecture where two covalently linked macrocycles have a single macrocycle passing through both rings (Figure 1). To the best of our knowledge, only two examples of such species—constructed using cationic templation—have been described in the chemical literature to date. Here, we detail the preparation and characterization of a novel chloride anion templated handcuff catenane, along with its crystal structure—this being the first handcuff catenane crystal structure to be determined.
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