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Article: Donor-acceptor oligorotaxanes made to order

TitleDonor-acceptor oligorotaxanes made to order
Authors
Keywordsfolding
noncovalent bonding interactions
oligomers
rotaxanes
template-directed syntheses
Issue Date2011
Citation
Chemistry - A European Journal, 2011, v. 17, n. 7, p. 2107-2119 How to Cite?
AbstractFive donor-acceptor oligorotaxanes made up of dumbbells composed of tetraethylene glycol chains, interspersed with three and five 1,5-dioxynaphthalene units, and terminated by 2,6-diisopropylphenoxy stoppers, have been prepared by the threading of discrete numbers of cyclobis(paraquat-p- phenylene) rings, followed by a kinetically controlled stoppering protocol that relies on click chemistry. The well-known copper(I)-catalyzed alkyne-azide cycloaddition between azide functions placed at the ends of the polyether chains and alkyne-bearing stopper precursors was employed during the final kinetically controlled template-directed synthesis of the five oligorotaxanes, which were characterized subsequently by 1HaNMR spectroscopy at low temperature (233aK) in deuterated acetonitrile. The secondary structures, as well as the conformations, of the five oligorotaxanes were unraveled by spectroscopic comparison with the dumbbell and ring components. By focusing attention on the changes in chemical shifts of some key probe protons, obtained from a wide range of low-temperature spectra, a picture emerges of a high degree of folding within the thread protons of the dumbbells of four of the five oligorotaxanesa the fifth oligorotaxane represents a control compound in effecta brought about by a combination of Ci-H···O and π-π stacking interactions between the π-electron-deficient bipyridinium units in the rings and the π-electron-rich 1,5-dioxynaphthalene units and polyether chains in the dumbbells. The secondary structures of a foldamer-like nature have received further support from a solid-state superstructure of a related [3]pseudorotaxane and density functional calculations performed thereon. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Persistent Identifierhttp://hdl.handle.net/10722/332937
ISSN
2023 Impact Factor: 3.9
2023 SCImago Journal Rankings: 1.058
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorBasu, Subhadeep-
dc.contributor.authorCoskun, Ali-
dc.contributor.authorFriedman, Douglas C.-
dc.contributor.authorOlson, Mark A.-
dc.contributor.authorBenítez, Diego-
dc.contributor.authorTkatchouk, Ekaterina-
dc.contributor.authorBarin, Gokhan-
dc.contributor.authorYang, Jeffrey-
dc.contributor.authorFahrenbach, Albert C.-
dc.contributor.authorGoddard, William A.-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-10-06T05:15:29Z-
dc.date.available2023-10-06T05:15:29Z-
dc.date.issued2011-
dc.identifier.citationChemistry - A European Journal, 2011, v. 17, n. 7, p. 2107-2119-
dc.identifier.issn0947-6539-
dc.identifier.urihttp://hdl.handle.net/10722/332937-
dc.description.abstractFive donor-acceptor oligorotaxanes made up of dumbbells composed of tetraethylene glycol chains, interspersed with three and five 1,5-dioxynaphthalene units, and terminated by 2,6-diisopropylphenoxy stoppers, have been prepared by the threading of discrete numbers of cyclobis(paraquat-p- phenylene) rings, followed by a kinetically controlled stoppering protocol that relies on click chemistry. The well-known copper(I)-catalyzed alkyne-azide cycloaddition between azide functions placed at the ends of the polyether chains and alkyne-bearing stopper precursors was employed during the final kinetically controlled template-directed synthesis of the five oligorotaxanes, which were characterized subsequently by 1HaNMR spectroscopy at low temperature (233aK) in deuterated acetonitrile. The secondary structures, as well as the conformations, of the five oligorotaxanes were unraveled by spectroscopic comparison with the dumbbell and ring components. By focusing attention on the changes in chemical shifts of some key probe protons, obtained from a wide range of low-temperature spectra, a picture emerges of a high degree of folding within the thread protons of the dumbbells of four of the five oligorotaxanesa the fifth oligorotaxane represents a control compound in effecta brought about by a combination of Ci-H···O and π-π stacking interactions between the π-electron-deficient bipyridinium units in the rings and the π-electron-rich 1,5-dioxynaphthalene units and polyether chains in the dumbbells. The secondary structures of a foldamer-like nature have received further support from a solid-state superstructure of a related [3]pseudorotaxane and density functional calculations performed thereon. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.-
dc.languageeng-
dc.relation.ispartofChemistry - A European Journal-
dc.subjectfolding-
dc.subjectnoncovalent bonding interactions-
dc.subjectoligomers-
dc.subjectrotaxanes-
dc.subjecttemplate-directed syntheses-
dc.titleDonor-acceptor oligorotaxanes made to order-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/chem.201001822-
dc.identifier.pmid21274953-
dc.identifier.scopuseid_2-s2.0-79551707310-
dc.identifier.volume17-
dc.identifier.issue7-
dc.identifier.spage2107-
dc.identifier.epage2119-
dc.identifier.eissn1521-3765-
dc.identifier.isiWOS:000287986500012-

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