An Acid−Base Switchable [2]Rotaxane
- 28 November 2002
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (26), 9175-9181
- https://doi.org/10.1021/jo020373d
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. (1)H 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 CDCl(3) solution.Keywords
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