An acid-base switchable [2]rotaxane

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

132 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 languageEnglish (US)
Pages (from-to)9175-9181
Number of pages7
JournalJournal of Organic Chemistry
Volume67
Issue number26
DOIs
StatePublished - Dec 27 2002

ASJC Scopus subject areas

  • Organic Chemistry

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