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Article: Syntheses of three-dimensional catenanes under kinetic control

TitleSyntheses of three-dimensional catenanes under kinetic control
Authors
KeywordsCationic cages
Mechanically interlocked molecules
Nontrivial topologies
Suitanes
Triple [π...π] interactions
Issue Date2022
Citation
Proceedings of the National Academy of Sciences of the United States of America, 2022, v. 119, n. 12, article no. e2118573119 How to Cite?
AbstractAlthough catenanes comprising two ring-shaped components can be made in large quantities by templation, the preparation of three-dimensional (3D) catenanes with cage-shaped components is still in its infancy. Here, we report the design and syntheses of two 3D catenanes by a sequence of SN2 reactions in one pot. The resulting triply mechanically interlocked molecules were fully characterized in both the solution and solid states. Mechanistic studies have revealed that a suit[3]ane, which contains a threefold symmetric cage component as the suit and a tribromide component as the body, is formed at elevated temperatures. This suit[3]ane was identified as the key reactive intermediate for the selective formation of the two 3D catenanes which do not represent thermodynamic minima. We foresee a future in which this particular synthetic strategy guides the rational design and production of mechanically interlocked molecules under kinetic control.
Persistent Identifierhttp://hdl.handle.net/10722/327739
ISSN
2023 Impact Factor: 9.4
2023 SCImago Journal Rankings: 3.737
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorWu, Yong-
dc.contributor.authorGuo, Qing Hui-
dc.contributor.authorQiu, Yunyan-
dc.contributor.authorWeber, Jacob A.-
dc.contributor.authorYoung, Ryan M.-
dc.contributor.authorBancroft, Laura-
dc.contributor.authorJiao, Yang-
dc.contributor.authorChen, Hongliang-
dc.contributor.authorSong, Bo-
dc.contributor.authorLiu, Wenqi-
dc.contributor.authorFeng, Yuanning-
dc.contributor.authorZhao, Xingang-
dc.contributor.authorLi, Xuesong-
dc.contributor.authorZhang, Long-
dc.contributor.authorChen, Xiao Yang-
dc.contributor.authorLi, Hao-
dc.contributor.authorWasielewski, Michael R.-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-04-24T05:09:38Z-
dc.date.available2023-04-24T05:09:38Z-
dc.date.issued2022-
dc.identifier.citationProceedings of the National Academy of Sciences of the United States of America, 2022, v. 119, n. 12, article no. e2118573119-
dc.identifier.issn0027-8424-
dc.identifier.urihttp://hdl.handle.net/10722/327739-
dc.description.abstractAlthough catenanes comprising two ring-shaped components can be made in large quantities by templation, the preparation of three-dimensional (3D) catenanes with cage-shaped components is still in its infancy. Here, we report the design and syntheses of two 3D catenanes by a sequence of SN2 reactions in one pot. The resulting triply mechanically interlocked molecules were fully characterized in both the solution and solid states. Mechanistic studies have revealed that a suit[3]ane, which contains a threefold symmetric cage component as the suit and a tribromide component as the body, is formed at elevated temperatures. This suit[3]ane was identified as the key reactive intermediate for the selective formation of the two 3D catenanes which do not represent thermodynamic minima. We foresee a future in which this particular synthetic strategy guides the rational design and production of mechanically interlocked molecules under kinetic control.-
dc.languageeng-
dc.relation.ispartofProceedings of the National Academy of Sciences of the United States of America-
dc.subjectCationic cages-
dc.subjectMechanically interlocked molecules-
dc.subjectNontrivial topologies-
dc.subjectSuitanes-
dc.subjectTriple [π...π] interactions-
dc.titleSyntheses of three-dimensional catenanes under kinetic control-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1073/pnas.2118573119-
dc.identifier.pmid35290119-
dc.identifier.scopuseid_2-s2.0-85126674272-
dc.identifier.volume119-
dc.identifier.issue12-
dc.identifier.spagearticle no. e2118573119-
dc.identifier.epagearticle no. e2118573119-
dc.identifier.eissn1091-6490-
dc.identifier.isiWOS:000775488100017-

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