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https://hdl.handle.net/2440/52346
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Type: | Journal article |
Title: | Synthesis of alpha-cyclodextrin [2]-rotaxanes using chlorotriazine capping reagents |
Author: | Dawson, R. Maniam, S. Lincoln, S. Easton, C. |
Citation: | Organic and Biomolecular Chemistry, 2008; 6(10):1814-1821 |
Publisher: | Royal Soc Chemistry |
Issue Date: | 2008 |
ISSN: | 1477-0520 1477-0539 |
Statement of Responsibility: | Ryan E. Dawson, Subashani Maniam, Stephen F. Lincoln and Christopher J. Easton |
Abstract: | Ten alpha-cyclodextrin [2]-rotaxanes have been prepared with alkane-, stilbene- and azobenzene-based axles, capped through nucleophilic substitution of either 2-chloro-4,6-dimethoxy-1,3,5-triazine or 2,4-dichloro-6-methoxy-1,3,5-triazine in aqueous solution, followed by further substitution of the remaining triazinyl chlorine in some cases when the latter capping reagent was used. In one case the rotaxane is a [c(2)]-daisy chain obtained by double-capping the corresponding hermaphroditic cyclic dimer. One of the rotaxane azobenzene derivatives was shown to undergo photochemically-induced reversible interconversion between its trans- and cis-isomers, causing the cyclodextrin to move back and forth along the axle, and therefore behave as a molecular shuttle. The methodology is therefore shown to constitute a general and versatile approach for the construction of supramolecular species as the basis of photochemical molecular devices. |
Description: | © Royal Society of Chemistry 2008 |
DOI: | 10.1039/b802229a |
Published version: | http://dx.doi.org/10.1039/b802229a |
Appears in Collections: | Aurora harvest Chemistry and Physics publications Environment Institute publications |
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