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Article: Molecular meccano, 57: Template-directed syntheses, spectroscopic properties, and electrochemical behavior of [n]catenanes

TitleMolecular meccano, 57: Template-directed syntheses, spectroscopic properties, and electrochemical behavior of [n]catenanes
Authors
KeywordsCatenanes
Cyclophanes
Electrochemistry
Electronic spectroscopy
Template- directed synthesis
Issue Date2000
Citation
European Journal of Organic Chemistry, 2000, n. 7, p. 1121-1130 How to Cite?
AbstractCatenanes composed of two, three, five, or seven interlocked macrocycles have been synthesized in yields ranging from 1 to 30%. Their template- directed syntheses rely on a series of cooperative noncovalent bonding interactions between π-electron rich 1,5-dioxynaphthalene ring systems and π-electron deficient bipyridinium units which are incorporated within the macrocyclic components. The interlocked structure associated with one of the [3]catenanes was demonstrated unequivocally by single crystal X-ray analysis which also revealed the formation of polar stacks stabilized by intermolecular [π···π] interactions. The number of interlocked components of each catenane was determined by liquid secondary ion, matrix- assisted laser desorption ionization/time-of-flight, and/or electrospray mass spectrometries. The absorption spectra, emission spectra, and electrochemical properties of the macrocyclic components and of the catenanes have been investigated. Two kinds of charge-transfer absorption bands (intramolecular in the cyclophanes containing electron-donor and electron-acceptor units, intercomponent in the catenanes) have been found. Such charge-transfer excited states are responsible for the quenching of the potentially fluorescence units of the cyclophanes, and of the crown ethers in the catenanes. Charge-transfer electronic interactions are also evidenced by the electrochemical behavior. Correlations among the redox potentials of the various compounds are reported and discussed.
Persistent Identifierhttp://hdl.handle.net/10722/332590
ISSN
2023 Impact Factor: 2.5
2023 SCImago Journal Rankings: 0.584
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorAshton, Peter R.-
dc.contributor.authorBaldoni, Virna-
dc.contributor.authorBalzani, Vincenzo-
dc.contributor.authorClaessens, Christian G.-
dc.contributor.authorCredi, Alberto-
dc.contributor.authorHoffmann, H. D.Andreas-
dc.contributor.authorRaymo, Françisco M.-
dc.contributor.authorStoddart, J. Fraser-
dc.contributor.authorVenturi, Margherita-
dc.contributor.authorWhite, Andrew J.P.-
dc.contributor.authorWilliams, David J.-
dc.date.accessioned2023-10-06T05:12:42Z-
dc.date.available2023-10-06T05:12:42Z-
dc.date.issued2000-
dc.identifier.citationEuropean Journal of Organic Chemistry, 2000, n. 7, p. 1121-1130-
dc.identifier.issn1434-193X-
dc.identifier.urihttp://hdl.handle.net/10722/332590-
dc.description.abstractCatenanes composed of two, three, five, or seven interlocked macrocycles have been synthesized in yields ranging from 1 to 30%. Their template- directed syntheses rely on a series of cooperative noncovalent bonding interactions between π-electron rich 1,5-dioxynaphthalene ring systems and π-electron deficient bipyridinium units which are incorporated within the macrocyclic components. The interlocked structure associated with one of the [3]catenanes was demonstrated unequivocally by single crystal X-ray analysis which also revealed the formation of polar stacks stabilized by intermolecular [π···π] interactions. The number of interlocked components of each catenane was determined by liquid secondary ion, matrix- assisted laser desorption ionization/time-of-flight, and/or electrospray mass spectrometries. The absorption spectra, emission spectra, and electrochemical properties of the macrocyclic components and of the catenanes have been investigated. Two kinds of charge-transfer absorption bands (intramolecular in the cyclophanes containing electron-donor and electron-acceptor units, intercomponent in the catenanes) have been found. Such charge-transfer excited states are responsible for the quenching of the potentially fluorescence units of the cyclophanes, and of the crown ethers in the catenanes. Charge-transfer electronic interactions are also evidenced by the electrochemical behavior. Correlations among the redox potentials of the various compounds are reported and discussed.-
dc.languageeng-
dc.relation.ispartofEuropean Journal of Organic Chemistry-
dc.subjectCatenanes-
dc.subjectCyclophanes-
dc.subjectElectrochemistry-
dc.subjectElectronic spectroscopy-
dc.subjectTemplate- directed synthesis-
dc.titleMolecular meccano, 57: Template-directed syntheses, spectroscopic properties, and electrochemical behavior of [n]catenanes-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/1099-0690(200004)2000:7<1121::aid-ejoc1121>3.0.co;2-3-
dc.identifier.scopuseid_2-s2.0-16344364726-
dc.identifier.issue7-
dc.identifier.spage1121-
dc.identifier.epage1130-
dc.identifier.isiWOS:000086857100004-

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