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- Publisher Website: 10.1002/chem.200204479
- Scopus: eid_2-s2.0-0141761378
- WOS: WOS:000185294800005
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Article: Kinetic versus thermodynamic control during the formation of [2]rotaxanes by a dynamic template-directed clipping process
Title | Kinetic versus thermodynamic control during the formation of [2]rotaxanes by a dynamic template-directed clipping process |
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Authors | |
Keywords | Crown compounds Dynamic covalent chemistry Rotaxanes Self-assembly Supramolecular chemistry |
Issue Date | 2003 |
Citation | Chemistry - A European Journal, 2003, v. 9, n. 17, p. 4046-4054 How to Cite? |
Abstract | A template-directed dynamic clipping procedure has generated a library of nine [2]rotaxanes that have been formed from three dialkylammonium salts - acting as the dumbbell-shaped components-and three dynamic, imino bond-containing, [24]crown-8-like macrocycles - acting as the ring-shaped components - which are themselves assembled from three dialdehydes and one diamine. The rates of formation of these [2]rotaxanes differ dramatically, from minutes to days depending on the choice of dialkylammonium ion and dialdehyde, as do their thermodynamic stabilities. Generally, [2]rotaxanes formed by using 2,6-diformylpyridine as the dialdehyde component, or bis(3,5-bis(trifluoromethyl)benzyl)ammonium hexafluorophosphate as the dumbbell-shaped component, assembled the most rapidly. Those rotaxanes containing this particular electron-deficient dumbbell-shaped unit, or 2,5-diformylfuran units in the macroring, were the most stable thermodynamically. The relative thermodynamic stabilities of all nine of the [2]rotaxanes were determined by competition experiments that were monitored by 1H NMR spectroscopy. |
Persistent Identifier | http://hdl.handle.net/10722/332544 |
ISSN | 2023 Impact Factor: 3.9 2023 SCImago Journal Rankings: 1.058 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Horn, Matthias | - |
dc.contributor.author | Ihringer, Johannes | - |
dc.contributor.author | Glink, Peter T. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:12:20Z | - |
dc.date.available | 2023-10-06T05:12:20Z | - |
dc.date.issued | 2003 | - |
dc.identifier.citation | Chemistry - A European Journal, 2003, v. 9, n. 17, p. 4046-4054 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332544 | - |
dc.description.abstract | A template-directed dynamic clipping procedure has generated a library of nine [2]rotaxanes that have been formed from three dialkylammonium salts - acting as the dumbbell-shaped components-and three dynamic, imino bond-containing, [24]crown-8-like macrocycles - acting as the ring-shaped components - which are themselves assembled from three dialdehydes and one diamine. The rates of formation of these [2]rotaxanes differ dramatically, from minutes to days depending on the choice of dialkylammonium ion and dialdehyde, as do their thermodynamic stabilities. Generally, [2]rotaxanes formed by using 2,6-diformylpyridine as the dialdehyde component, or bis(3,5-bis(trifluoromethyl)benzyl)ammonium hexafluorophosphate as the dumbbell-shaped component, assembled the most rapidly. Those rotaxanes containing this particular electron-deficient dumbbell-shaped unit, or 2,5-diformylfuran units in the macroring, were the most stable thermodynamically. The relative thermodynamic stabilities of all nine of the [2]rotaxanes were determined by competition experiments that were monitored by 1H NMR spectroscopy. | - |
dc.language | eng | - |
dc.relation.ispartof | Chemistry - A European Journal | - |
dc.subject | Crown compounds | - |
dc.subject | Dynamic covalent chemistry | - |
dc.subject | Rotaxanes | - |
dc.subject | Self-assembly | - |
dc.subject | Supramolecular chemistry | - |
dc.title | Kinetic versus thermodynamic control during the formation of [2]rotaxanes by a dynamic template-directed clipping process | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/chem.200204479 | - |
dc.identifier.scopus | eid_2-s2.0-0141761378 | - |
dc.identifier.volume | 9 | - |
dc.identifier.issue | 17 | - |
dc.identifier.spage | 4046 | - |
dc.identifier.epage | 4054 | - |
dc.identifier.isi | WOS:000185294800005 | - |