Quantitative emergence of hetero[4]rotaxanes by template-directed click chemistry

Chenfeng Ke; Ronald A Smaldone; Takashi Kikuchi; Hao Li; Anthony P Davis; J Fraser Stoddart

doi:10.1002/anie.201205087

Quantitative emergence of hetero[4]rotaxanes by template-directed click chemistry

Angew Chem Int Ed Engl. 2013 Jan 2;52(1):381-7. doi: 10.1002/anie.201205087. Epub 2012 Sep 13.

Authors

Chenfeng Ke¹, Ronald A Smaldone, Takashi Kikuchi, Hao Li, Anthony P Davis, J Fraser Stoddart

Affiliation

¹ Center for the Chemistry of Integrated Systems, Department of Chemistry, Northwestern University, Evanston, IL 60208, USA.

PMID: 22976927
DOI: 10.1002/anie.201205087

Abstract

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 in one pot affords a hetero[4]rotaxane in one minute in quantitative yield.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Click Chemistry / methods*
Kinetics
Rotaxanes / chemistry*
Thermodynamics

Substances

Rotaxanes