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- Publisher Website: 10.1002/chem.200800067
- Scopus: eid_2-s2.0-53649094761
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Article: A one-pot synthesis of constitutionally unsymmetrical rotaxanes using sequential Cui-catalyzed azide-alkyne cycloadditions
Title | A one-pot synthesis of constitutionally unsymmetrical rotaxanes using sequential Cu<sup>i</sup>-catalyzed azide-alkyne cycloadditions |
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Authors | |
Keywords | Cycloaddition Mechanical bonds Rotaxanes Supramolecular chemistry Template-directed synthesis |
Issue Date | 2008 |
Citation | Chemistry - A European Journal, 2008, v. 14, n. 14, p. 4168-4177 How to Cite? |
Abstract | A one-pot sequential CuI-catalyzed azide-alkyne cycloaddition (CuAAC) strategy is presented for the synthesis of constitutionally unsymmetrical cyclobis(paraquat-p-phenylene)-based rotaxanes in good yields from simple starting materials. The methodology consists of performing multiple CuAAC reactions to stopper a pseudorotaxane in a stepwise manner, the order of which is controlled through silyl-protection and AgI-catalyzed deprotection of a terminal alkyne. The methodology is highlighted by the synthesis of an amphiphilic branched [4]rotaxane. The methodology increases the ability to access ever more complicated mechanically interlocked compounds to serve in devices as sophisticated and functional molecular machinery. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA,. |
Persistent Identifier | http://hdl.handle.net/10722/332857 |
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 | Spruell, Jason M. | - |
dc.contributor.author | Dichtel, William R. | - |
dc.contributor.author | Heath, James R. | - |
dc.contributor.author | Stoddart, J. Fraser | - |
dc.date.accessioned | 2023-10-06T05:14:48Z | - |
dc.date.available | 2023-10-06T05:14:48Z | - |
dc.date.issued | 2008 | - |
dc.identifier.citation | Chemistry - A European Journal, 2008, v. 14, n. 14, p. 4168-4177 | - |
dc.identifier.issn | 0947-6539 | - |
dc.identifier.uri | http://hdl.handle.net/10722/332857 | - |
dc.description.abstract | A one-pot sequential CuI-catalyzed azide-alkyne cycloaddition (CuAAC) strategy is presented for the synthesis of constitutionally unsymmetrical cyclobis(paraquat-p-phenylene)-based rotaxanes in good yields from simple starting materials. The methodology consists of performing multiple CuAAC reactions to stopper a pseudorotaxane in a stepwise manner, the order of which is controlled through silyl-protection and AgI-catalyzed deprotection of a terminal alkyne. The methodology is highlighted by the synthesis of an amphiphilic branched [4]rotaxane. The methodology increases the ability to access ever more complicated mechanically interlocked compounds to serve in devices as sophisticated and functional molecular machinery. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA,. | - |
dc.language | eng | - |
dc.relation.ispartof | Chemistry - A European Journal | - |
dc.subject | Cycloaddition | - |
dc.subject | Mechanical bonds | - |
dc.subject | Rotaxanes | - |
dc.subject | Supramolecular chemistry | - |
dc.subject | Template-directed synthesis | - |
dc.title | A one-pot synthesis of constitutionally unsymmetrical rotaxanes using sequential Cu<sup>i</sup>-catalyzed azide-alkyne cycloadditions | - |
dc.type | Article | - |
dc.description.nature | link_to_subscribed_fulltext | - |
dc.identifier.doi | 10.1002/chem.200800067 | - |
dc.identifier.scopus | eid_2-s2.0-53649094761 | - |
dc.identifier.volume | 14 | - |
dc.identifier.issue | 14 | - |
dc.identifier.spage | 4168 | - |
dc.identifier.epage | 4177 | - |
dc.identifier.eissn | 1521-3765 | - |
dc.identifier.isi | WOS:000256131800006 | - |