Catenane Closure via Chloride

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Science  19 Nov 2004:
Vol. 306, Issue 5700, pp. 1261
DOI: 10.1126/science.306.5700.1261a

The assembly of interlocking molecular rings, or catenanes, normally relies on some sort of templating mechanism to hold the components together while chemical reactions complete the cyclization. Sambrook et al. report on the use of anions as templating agents. They use a catenane precursor and a macrocyclic ring, each of which bears a cleft region that brings two amide groups into close proximity. Binding of a single chloride ion by these four amides holds the precursor onto the macrocyclic ring; this interaction is also stabilized by π-π stacking interactions between hydroquinone groups on both molecules. Ring-closing metathesis cyclizes the precursor, either as a monomer to form two interlocked rings or as a dimer to form a [3]catenane. The [2]catenane product selectively binds chloride anions over acetate and dihydrogen phosphate. — PDS

J. Am. Chem. Soc. 10.1021/ja045080b (2004).

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