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Quantitative Emergence of Hetero[4]rotaxanes by Template-Directed Click Chemistry

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  • This work was supported under the auspices of an international collaboration supported in the US by the National Science Foundation (NSF) under grant CHE-0924620 and in the UK by the Engineering and Physical Sciences Research Council (EPSRC) under grant EP/H003517/1. C.K. thanks the Royal Society in the UK for support as a Newton Fellow Alumnus. J.F.S. acknowledges the World Class University (WCU) Program (R-31-2008-000-10055-0) in Korea.

Abstract

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In one fell swoop, polyrotaxanes comprising up to 64 rings can be synthesized as a result of cucurbit[6]uril-templated 1,3-dipolar azide-alkyne cycloadditions accelerated in the presence of cyclodextrins as a consequence of self-sorting and positive cooperativity, brought about by hydrogen bonding. Mixing six components (see picture) in one pot affords a hetero[4]rotaxane in one minute in quantitative yield.

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