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Article: Modular synthesis and dynamics of a variety of donor-acceptor interlocked compounds prepared by click chemistry

TitleModular synthesis and dynamics of a variety of donor-acceptor interlocked compounds prepared by click chemistry
Authors
KeywordsClick chemistry
Cycloaddition
Host-guest systems
Interlocked compounds
Rotaxanes
Issue Date2007
Citation
Chemistry - An Asian Journal, 2007, v. 2, n. 5, p. 634-647 How to Cite?
AbstractA series of donor-acceptor [2]-, [3]-, and [4]rotaxanes and self-complexes ([1]rotaxanes) have been synthesized by a threading-followed-by-stoppering approach, in which the precursor pseudorotaxanes are fixed by using Cu I-catalyzed Huisgen 1,3-dipolar cycloaddition to attach the required stoppers. This alternative approach to forming rotaxanes of the donor-acceptor type, in which the donor is a 1,5-dioxynaphthalene unit and the acceptor is the tetracationic cyclophane cyclobis(paraquat-p-phenylene), proceeds with enhanced yields relative to the tried and tested synthetic strategies, which involve the clipping of the cyclophane around a preformed dumbbell containing π-electron-donating recognition sites. The new synthetic approach is amenable to application to highly convergent sequences. To extend the scope of this reaction, we constructed [2]rotaxanes in which one of the phenylene rings of the tetracationic cyclophane is perfluorinated, a feature which significantly weakens its association with π-electron-rich guests. The activation barrier for the shuttling of the cyclophane over a spacer containing two triazole rings was determined to be (15.5 ± 0.1) kcal mol-1 for a degenerate two-station [2]rotaxane, a value similar to that previously measured for analogous degenerate compounds containing aromatic or ethylene glycol spacers. The triazole rings do not seem to perturb the shuttling process significantly; this property bodes well for their future incorporation into bistable molecular switches. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
Persistent Identifierhttp://hdl.handle.net/10722/332734
ISSN
2023 Impact Factor: 3.5
2023 SCImago Journal Rankings: 0.846
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorBraunschweig, Adam B.-
dc.contributor.authorDichtel, William R.-
dc.contributor.authorMiljanić, Ognjen Š-
dc.contributor.authorOlson, Mark A.-
dc.contributor.authorSpruell, Jason M.-
dc.contributor.authorKhan, Saeed I.-
dc.contributor.authorHeath, James R.-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-10-06T05:13:52Z-
dc.date.available2023-10-06T05:13:52Z-
dc.date.issued2007-
dc.identifier.citationChemistry - An Asian Journal, 2007, v. 2, n. 5, p. 634-647-
dc.identifier.issn1861-4728-
dc.identifier.urihttp://hdl.handle.net/10722/332734-
dc.description.abstractA series of donor-acceptor [2]-, [3]-, and [4]rotaxanes and self-complexes ([1]rotaxanes) have been synthesized by a threading-followed-by-stoppering approach, in which the precursor pseudorotaxanes are fixed by using Cu I-catalyzed Huisgen 1,3-dipolar cycloaddition to attach the required stoppers. This alternative approach to forming rotaxanes of the donor-acceptor type, in which the donor is a 1,5-dioxynaphthalene unit and the acceptor is the tetracationic cyclophane cyclobis(paraquat-p-phenylene), proceeds with enhanced yields relative to the tried and tested synthetic strategies, which involve the clipping of the cyclophane around a preformed dumbbell containing π-electron-donating recognition sites. The new synthetic approach is amenable to application to highly convergent sequences. To extend the scope of this reaction, we constructed [2]rotaxanes in which one of the phenylene rings of the tetracationic cyclophane is perfluorinated, a feature which significantly weakens its association with π-electron-rich guests. The activation barrier for the shuttling of the cyclophane over a spacer containing two triazole rings was determined to be (15.5 ± 0.1) kcal mol-1 for a degenerate two-station [2]rotaxane, a value similar to that previously measured for analogous degenerate compounds containing aromatic or ethylene glycol spacers. The triazole rings do not seem to perturb the shuttling process significantly; this property bodes well for their future incorporation into bistable molecular switches. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.-
dc.languageeng-
dc.relation.ispartofChemistry - An Asian Journal-
dc.subjectClick chemistry-
dc.subjectCycloaddition-
dc.subjectHost-guest systems-
dc.subjectInterlocked compounds-
dc.subjectRotaxanes-
dc.titleModular synthesis and dynamics of a variety of donor-acceptor interlocked compounds prepared by click chemistry-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/asia.200700035-
dc.identifier.scopuseid_2-s2.0-34250813187-
dc.identifier.volume2-
dc.identifier.issue5-
dc.identifier.spage634-
dc.identifier.epage647-
dc.identifier.eissn1861-471X-
dc.identifier.isiWOS:000246543300008-

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