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Installation of a Ratchet Tooth and Pawl To Restrict Rotation in a Cyclodextrin Rotaxane
Author(s) -
Onagi Hideki,
Blake Christopher J.,
Easton Christopher J.,
Lincoln Stephen F.
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200305280
Subject(s) - ratchet , rotaxane , cyclodextrin , chemistry , rotor (electric) , axle , rotation (mathematics) , stereochemistry , crystallography , computer science , physics , organic chemistry , artificial intelligence , supramolecular chemistry , crystal structure , quantum mechanics , chaotic , thermodynamics
Eight new [2]rotaxanes have been prepared, incorporating an α‐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.