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*

*Corresponding author for this work

Research output: Contribution to journalArticle

80 Scopus citations

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 (see picture) in one pot affords a hetero[4]rotaxane in one minute in quantitative yield.

Original languageEnglish (US)
Pages (from-to)381-387
Number of pages7
JournalAngewandte Chemie - International Edition
Volume52
Issue number1
DOIs
StatePublished - Jan 2 2013

Keywords

  • Cucurbiturils
  • Cyclodextrins
  • Kinetic covalent chemistry
  • Positive cooperativity
  • Self-sorting

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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