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Article: Efficient production of [n]rotaxanes by using template-directed clipping reactions

TitleEfficient production of [n]rotaxanes by using template-directed clipping reactions
Authors
KeywordsDynamic covalent chemistry
Molecular recognition
Polyrotaxanes
Self-assembly
Template-directed synthesis
Issue Date2007
Citation
Proceedings of the National Academy of Sciences of the United States of America, 2007, v. 104, n. 44, p. 17266-17271 How to Cite?
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.
Persistent Identifierhttp://hdl.handle.net/10722/332752
ISSN
2023 Impact Factor: 9.4
2023 SCImago Journal Rankings: 3.737
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorWu, Jishan-
dc.contributor.authorLeung, Ken Cham Fai-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-10-06T05:14:00Z-
dc.date.available2023-10-06T05:14:00Z-
dc.date.issued2007-
dc.identifier.citationProceedings of the National Academy of Sciences of the United States of America, 2007, v. 104, n. 44, p. 17266-17271-
dc.identifier.issn0027-8424-
dc.identifier.urihttp://hdl.handle.net/10722/332752-
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.languageeng-
dc.relation.ispartofProceedings of the National Academy of Sciences of the United States of America-
dc.subjectDynamic covalent chemistry-
dc.subjectMolecular recognition-
dc.subjectPolyrotaxanes-
dc.subjectSelf-assembly-
dc.subjectTemplate-directed synthesis-
dc.titleEfficient production of [n]rotaxanes by using template-directed clipping reactions-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1073/pnas.0705847104-
dc.identifier.pmid17947382-
dc.identifier.scopuseid_2-s2.0-36849079213-
dc.identifier.volume104-
dc.identifier.issue44-
dc.identifier.spage17266-
dc.identifier.epage17271-
dc.identifier.eissn1091-6490-
dc.identifier.isiWOS:000250638400008-

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