An acid-base switchable [2]rotaxane

Arkadij M. Elizarov; Sheng Hsien Chiu; J. Fraser Stoddart

doi:10.1021/jo020373d

An acid-base switchable [2]rotaxane

Arkadij M. Elizarov, Sheng Hsien Chiu, J. Fraser Stoddart^*

^*Corresponding author for this work

Chemistry

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

142 Scopus citations

Abstract

A chemically addressable, bistable [2]rotaxane, which incorporates a dumbbell-shaped component containing both secondary dialkylammonium and 1,2-bis(pyridinium)ethane recognition sites for its ring component, dibenzo[24]crown-8 (DB24C8), has been assembled. ¹H NMR spectroscopy has demonstrated that deprotonation (and reprotonation) of the secondary dialkylammonium (dialkylamine) recognition site induces the DB24C8 ring to move away from this site to the 1,2-bis-(pyridinium)ethane one (and back again) in a discrete manner, particularly when the experiment is performed in CDC13 solution.

Original language	English (US)
Pages (from-to)	9175-9181
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	67
Issue number	26
DOIs	https://doi.org/10.1021/jo020373d
State	Published - Dec 27 2002

ASJC Scopus subject areas

Organic Chemistry

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abstract = "A chemically addressable, bistable [2]rotaxane, which incorporates a dumbbell-shaped component containing both secondary dialkylammonium and 1,2-bis(pyridinium)ethane recognition sites for its ring component, dibenzo[24]crown-8 (DB24C8), has been assembled. 1H NMR spectroscopy has demonstrated that deprotonation (and reprotonation) of the secondary dialkylammonium (dialkylamine) recognition site induces the DB24C8 ring to move away from this site to the 1,2-bis-(pyridinium)ethane one (and back again) in a discrete manner, particularly when the experiment is performed in CDC13 solution.",

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AU - Elizarov, Arkadij M.

AU - Chiu, Sheng Hsien

AU - Stoddart, J. Fraser

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Y1 - 2002/12/27

N2 - A chemically addressable, bistable [2]rotaxane, which incorporates a dumbbell-shaped component containing both secondary dialkylammonium and 1,2-bis(pyridinium)ethane recognition sites for its ring component, dibenzo[24]crown-8 (DB24C8), has been assembled. 1H NMR spectroscopy has demonstrated that deprotonation (and reprotonation) of the secondary dialkylammonium (dialkylamine) recognition site induces the DB24C8 ring to move away from this site to the 1,2-bis-(pyridinium)ethane one (and back again) in a discrete manner, particularly when the experiment is performed in CDC13 solution.

AB - A chemically addressable, bistable [2]rotaxane, which incorporates a dumbbell-shaped component containing both secondary dialkylammonium and 1,2-bis(pyridinium)ethane recognition sites for its ring component, dibenzo[24]crown-8 (DB24C8), has been assembled. 1H NMR spectroscopy has demonstrated that deprotonation (and reprotonation) of the secondary dialkylammonium (dialkylamine) recognition site induces the DB24C8 ring to move away from this site to the 1,2-bis-(pyridinium)ethane one (and back again) in a discrete manner, particularly when the experiment is performed in CDC13 solution.

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An acid-base switchable [2]rotaxane

Abstract

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