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

Chenfeng Ke, Ronald A. Smaldone, Takashi Kikuchi, Hao Li, Anthony P. Davis, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

102 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 language	English (US)
Pages (from-to)	381-387
Number of pages	7
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	1
DOIs	https://doi.org/10.1002/anie.201205087
State	Published - Jan 2 2013

Keywords

Cucurbiturils
Cyclodextrins
Kinetic covalent chemistry
Positive cooperativity
Self-sorting

ASJC Scopus subject areas

General Chemistry
Catalysis

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10.1002/anie.201205087

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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.",

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AU - Ke, Chenfeng

AU - Smaldone, Ronald A.

AU - Kikuchi, Takashi

AU - Li, Hao

AU - Davis, Anthony P.

AU - Stoddart, J. Fraser

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AB - 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.

KW - Cucurbiturils

KW - Cyclodextrins

KW - Kinetic covalent chemistry

KW - Positive cooperativity

KW - Self-sorting

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

Abstract

Keywords

ASJC Scopus subject areas

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