Please use this identifier to cite or link to this item: https://doi.org/10.1073/pnas.0705847104
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dc.titleEfficient production of [n]rotaxanes by using template-directed clipping reactions
dc.contributor.authorWu, J.
dc.contributor.authorLeung, K.C.-F.
dc.contributor.authorStoddart, J.F.
dc.date.accessioned2014-10-16T08:27:06Z
dc.date.available2014-10-16T08:27:06Z
dc.date.issued2007-10-30
dc.identifier.citationWu, 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. https://doi.org/10.1073/pnas.0705847104
dc.identifier.issn00278424
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/93678
dc.description.abstractIn 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.
dc.description.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1073/pnas.0705847104
dc.sourceScopus
dc.subjectDynamic covalent chemistry
dc.subjectMolecular recognition
dc.subjectPolyrotaxanes
dc.subjectSelf-assembly
dc.subjectTemplate-directed synthesis
dc.typeArticle
dc.contributor.departmentCHEMISTRY
dc.description.doi10.1073/pnas.0705847104
dc.description.sourcetitleProceedings of the National Academy of Sciences of the United States of America
dc.description.volume104
dc.description.issue44
dc.description.page17266-17271
dc.description.codenPNASA
dc.identifier.isiut000250638400008
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