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Installation of a ratchet tooth and pawl to restrict rotation in a cyclodextrin rotaxane.

Chemistry (Weinheim an der Bergstrasse, Germany) (2003-12-18)
Hideki Onagi, Christopher J Blake, Christopher J Easton, Stephen F Lincoln
ABSTRACT

Eight new [2]rotaxanes have been prepared, incorporating an alpha-cyclodextrin as the rotor, a stilbene as the axle, and trinitrophenyl substituents as capping groups. Strategies have been devised to elaborate these by linking the rotor to the axle, to produce two new [1]rotaxanes. Rotational motion in a selection of these rotaxanes has been investigated through the application of two-dimensional NMR spectroscopy by performing TOCSY, DQF-COSY, ROESY and HMQC experiments. This has shown that a methoxyl group incorporated on the stilbene and a succinamide joining the stilbene and the cyclodextrin behave analogously to a ratchet tooth and pawl, respectively, to restrict rotation.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Succinamide, 98%