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Title: Efficient production of [n]rotaxanes by using template-directed clipping reactions
Authors: Wu, J. 
Leung, K.C.-F.
Stoddart, J.F.
Keywords: Dynamic covalent chemistry
Molecular recognition
Template-directed synthesis
Issue Date: 30-Oct-2007
Citation: Wu, J., Leung, K.C.-F., Stoddart, J.F. (2007-10-30). Efficient production of [n]rotaxanes by using template-directed clipping reactions. Proceedings of the National Academy of Sciences of the United States of America 104 (44) : 17266-17271. ScholarBank@NUS Repository.
Abstract: In this article, we report on the efficient synthesis of well defined, homogeneous [n]rotaxanes (n up to 11) by a template-directed thermodynamic clipping approach. By employing dynamic covalent chemistry in the form of reversible imine bond formation, [n]rotaxanes with dialkylammonium ion (-CH 2NH2 +CH2-) recognition sites, encircled by [24]crown-8 rings, were prepared by a thermodynamically controlled, template-directed clipping procedure, that is, by mixing together a dumbbell compound containing a discrete number of -CH2NH2 +CH2- ion centers with appropriate amounts of a dialdehyde and a diamine to facilitate the [n]rotaxane formation. A 21-component self-assembly process is operative during the formation of the [11]rotaxane. The oligomeric dumbbells containing -CH2NH2 +CH2- ion recognition sites were prepared by a stepwise protocol. Several of the dynamic [n]rotaxanes were converted into their kinetically stable counterparts, first by reduction ("fixing") of imine bonds with the BH3·THF complex, then by protonation of the complex by addition of acid. © 2007 by The National Academy of Sciences of the USA.
Source Title: Proceedings of the National Academy of Sciences of the United States of America
ISSN: 00278424
DOI: 10.1073/pnas.0705847104
Appears in Collections:Staff Publications

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