Please use this identifier to cite or link to this item:
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
Source: 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

Show full item record
Files in This Item:
There are no files associated with this item.


checked on Mar 8, 2018


checked on Feb 7, 2018

Page view(s)

checked on Mar 12, 2018

Google ScholarTM



Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.