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- Publisher Website: 10.1002/pat.260
- Scopus: eid_2-s2.0-0036825979
- WOS: WOS:000180679000014
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Article: Surrogate-stoppered [2]rotaxanes: A new route to larger interlocked architectures
Title | Surrogate-stoppered [2]rotaxanes: A new route to larger interlocked architectures |
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Authors | |
Keywords | Macrocycles Oligomers Polyrotaxanes Supramolecular structure Wittig reaction |
Issue Date | 2002 |
Citation | Polymers for Advanced Technologies, 2002, v. 13, n. 10-12, p. 777-787 How to Cite? |
Abstract | A novel synthetic strategy for exchanging stoppers on rotaxanes, without them losing their integrity as interlocked molecules, is presented. The surrogate-stoppered [2] rotaxane contains one inert stopper and a triphenylphosphonium group attached to a benzylic position as a second reactive stopper in the dumbbell-shaped component which contains an ammonium (NH2+) ion recognition site, encircled by a crown ether (24C8 or 25C8) component. The strategy for exchanging stoppers relies upon the ability of a benzylic triphenyl-phosphonium function to undergo a Wittig reaction with a bulky aromatic aldehyde to form a 'stilbenoid' [2] rotaxane as a mixture of cis and trans isomers, without the occurrence of any dethreading of the crown ether ring component. The C=C double bonds can then be hydrogenated, using Adams' catalyst, to afford a new covalently modified [2]rotaxane with two inert stoppers. Utilizing this strategy, larger interlocked molecular structures including a two-stationed [2]rotaxane and a branched [4]rotaxane have been prepared. Furthermore, initial studies, aimed at using this methodology to gain access to poly[n]rotaxane architectures, are presented. |
Persistent Identifier | http://hdl.handle.net/10722/332509 |
ISSN | 2023 Impact Factor: 3.1 2023 SCImago Journal Rankings: 0.584 |
ISI Accession Number ID |
DC Field | Value | Language |
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dc.contributor.author | Rowan, Stuart J. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:12:04Z | - |
dc.date.available | 2023-10-06T05:12:04Z | - |
dc.date.issued | 2002 | - |
dc.identifier.citation | Polymers for Advanced Technologies, 2002, v. 13, n. 10-12, p. 777-787 | - |
dc.identifier.issn | 1042-7147 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332509 | - |
dc.description.abstract | A novel synthetic strategy for exchanging stoppers on rotaxanes, without them losing their integrity as interlocked molecules, is presented. The surrogate-stoppered [2] rotaxane contains one inert stopper and a triphenylphosphonium group attached to a benzylic position as a second reactive stopper in the dumbbell-shaped component which contains an ammonium (NH2+) ion recognition site, encircled by a crown ether (24C8 or 25C8) component. The strategy for exchanging stoppers relies upon the ability of a benzylic triphenyl-phosphonium function to undergo a Wittig reaction with a bulky aromatic aldehyde to form a 'stilbenoid' [2] rotaxane as a mixture of cis and trans isomers, without the occurrence of any dethreading of the crown ether ring component. The C=C double bonds can then be hydrogenated, using Adams' catalyst, to afford a new covalently modified [2]rotaxane with two inert stoppers. Utilizing this strategy, larger interlocked molecular structures including a two-stationed [2]rotaxane and a branched [4]rotaxane have been prepared. Furthermore, initial studies, aimed at using this methodology to gain access to poly[n]rotaxane architectures, are presented. | - |
dc.language | eng | - |
dc.relation.ispartof | Polymers for Advanced Technologies | - |
dc.subject | Macrocycles | - |
dc.subject | Oligomers | - |
dc.subject | Polyrotaxanes | - |
dc.subject | Supramolecular structure | - |
dc.subject | Wittig reaction | - |
dc.title | Surrogate-stoppered [2]rotaxanes: A new route to larger interlocked architectures | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/pat.260 | - |
dc.identifier.scopus | eid_2-s2.0-0036825979 | - |
dc.identifier.volume | 13 | - |
dc.identifier.issue | 10-12 | - |
dc.identifier.spage | 777 | - |
dc.identifier.epage | 787 | - |
dc.identifier.isi | WOS:000180679000014 | - |