dc.contributor.author |
Kanagaraj, Kuppusamy |
dc.contributor.author |
Wang, Rui |
dc.contributor.author |
Zhao, Ming-Kai |
dc.contributor.author |
Ballester, Pablo |
dc.contributor.author |
Rebek, Julius Jr. |
dc.contributor.author |
Yu, Yang |
dc.date.accessioned |
2023-04-24T13:11:54Z |
dc.date.available |
2024-02-29T01:45:05Z |
dc.date.issued |
2023-03-01 |
dc.identifier.uri |
http://hdl.handle.net/2072/533096 |
dc.format.extent |
8 p. |
dc.language.iso |
eng |
dc.publisher |
ACS Publications |
dc.rights |
Creative Commons
Reconocimiento-NoComercial-SinObraDerivada 4.0 Internacional.
Esta licencia está permanentemente ubicada en
http://creativecommons.org/licenses/by-nc-nd/4.0/. |
dc.source |
RECERCAT (Dipòsit de la Recerca de Catalunya) |
dc.subject.other |
Química |
dc.title |
Selective Binding and Isomerization of Oximes in a Self-Assembled Capsule |
dc.type |
info:eu-repo/semantics/article |
dc.type |
info:eu-repo/semantics/acceptedVersion |
dc.subject.udc |
00 - Ciència i coneixement. Investigació. Cultura. Humanitats |
dc.embargo.terms |
12 mesos |
dc.identifier.doi |
10.1021/jacs.2c12907 |
dc.rights.accessLevel |
info:eu-repo/semantics/openAccess |
dc.description.abstract |
A series of straight-chain (C7–C13) alkyl-O-methyl aldoximes (R–C(H)═NOMe) were synthesized with various functional groups at the remote ends (alkenes, halogen, −COOH, and NH2). Their isomers about the C═N bond showed ∼60–40% E–Z-ratio in organic solutions. Surprisingly, their confinement in a water-soluble capsule with benzoselenodiazole walls shows high selectivity for the cis-/Z-isomer. Their relative affinities for the chalcogen-bonded capsule at room temperature depend mainly on the guest chain length and functional groups. A chain length of 14 heavy atoms showed especially high E- to Z-isomer selectivity (>99%) and was used in separation. The E–Z isomerization occurred only in the capsular cavity at room temperature and was accelerated 10-fold by sonication. The Z-isomer selective binding, separation, and E–Z isomerization are supported by NMR, DOSY, and computational studies. |