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Article: Self-assembly and self-organization of self-recognizing cyclophanes

TitleSelf-assembly and self-organization of self-recognizing cyclophanes
Authors
KeywordsCrystal engineering
Host-guest chemistry
Nanotubes
Sandwich complexes
Self-assembly
Issue Date1998
Citation
European Journal of Organic Chemistry, 1998, n. 6, p. 969-981 How to Cite?
AbstractAn analysis is presented of the different contributions that give rise to the packing observed in the crystal structures of a wide range of bipyridinium-based molecular assemblies and supramolecular arrays. It is demonstrated how the various interactions - electrostatic, van der Waals, and π-π interactions - that contribute to the solid-state arrangement of these molecules and supermolecules can be utilized in order to design a series of tetracationic cyclophanes that can potentially self-organize in a highly ordered way in the solid state by virtue of the fact that they contain π-electron donors as well as π-electron acceptors. The syntheses of these cyclophanes is outlined and the tunability of the self-assembly methodology in their construction is demonstrated. One of these tetracationic cyclophanes - comprising π-electron-rich hydroquinone rings and π-electron-deficient bipyridinium units - has been shown to pack as highly ordered two-dimensional, mosaic-like sheets in the solid state. Its dicationic precursor also forms extended π-π-stacked layers in the solid state. An analogous cyclophane - containing two π-electron-rich resorcinol rings in place of the two hydroquinone rings - forms, in the solid state, one-dimensional arrays wherein the component resorcinol rings interact through then: parallel π-π stacking. It has also been established that the first of the aforementioned tetracationic cyclophanes forms a 1:1 adduct with ferrocene in both the solution and solid states. X-ray crystallography, performed on the 1:1 adduct, reveals that not only is the ferrocene molecule complexed in a π-π slacking sense within the tetracationic cyclophane, but the 1:1 adduct also packs in a manner that is remarkably similar to the supramolecular organization of the free cyclophane in the crystalline state.
Persistent Identifierhttp://hdl.handle.net/10722/333582
ISSN
2023 Impact Factor: 2.5
2023 SCImago Journal Rankings: 0.584

 

DC FieldValueLanguage
dc.contributor.authorAshton, Peter R.-
dc.contributor.authorChemin, Alexandre-
dc.contributor.authorClaessens, Christian G.-
dc.contributor.authorMenzer, Stephan-
dc.contributor.authorStoddart, J. Fraser-
dc.contributor.authorWhite, Andrew J.P.-
dc.contributor.authorWilliams, David J.-
dc.date.accessioned2023-10-06T05:20:46Z-
dc.date.available2023-10-06T05:20:46Z-
dc.date.issued1998-
dc.identifier.citationEuropean Journal of Organic Chemistry, 1998, n. 6, p. 969-981-
dc.identifier.issn1434-193X-
dc.identifier.urihttp://hdl.handle.net/10722/333582-
dc.description.abstractAn analysis is presented of the different contributions that give rise to the packing observed in the crystal structures of a wide range of bipyridinium-based molecular assemblies and supramolecular arrays. It is demonstrated how the various interactions - electrostatic, van der Waals, and π-π interactions - that contribute to the solid-state arrangement of these molecules and supermolecules can be utilized in order to design a series of tetracationic cyclophanes that can potentially self-organize in a highly ordered way in the solid state by virtue of the fact that they contain π-electron donors as well as π-electron acceptors. The syntheses of these cyclophanes is outlined and the tunability of the self-assembly methodology in their construction is demonstrated. One of these tetracationic cyclophanes - comprising π-electron-rich hydroquinone rings and π-electron-deficient bipyridinium units - has been shown to pack as highly ordered two-dimensional, mosaic-like sheets in the solid state. Its dicationic precursor also forms extended π-π-stacked layers in the solid state. An analogous cyclophane - containing two π-electron-rich resorcinol rings in place of the two hydroquinone rings - forms, in the solid state, one-dimensional arrays wherein the component resorcinol rings interact through then: parallel π-π stacking. It has also been established that the first of the aforementioned tetracationic cyclophanes forms a 1:1 adduct with ferrocene in both the solution and solid states. X-ray crystallography, performed on the 1:1 adduct, reveals that not only is the ferrocene molecule complexed in a π-π slacking sense within the tetracationic cyclophane, but the 1:1 adduct also packs in a manner that is remarkably similar to the supramolecular organization of the free cyclophane in the crystalline state.-
dc.languageeng-
dc.relation.ispartofEuropean Journal of Organic Chemistry-
dc.subjectCrystal engineering-
dc.subjectHost-guest chemistry-
dc.subjectNanotubes-
dc.subjectSandwich complexes-
dc.subjectSelf-assembly-
dc.titleSelf-assembly and self-organization of self-recognizing cyclophanes-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1002/(SICI)1099-0690(199806)1998:6<969::AID-EJOC969>3.0.CO;2-G-
dc.identifier.scopuseid_2-s2.0-0008623723-
dc.identifier.issue6-
dc.identifier.spage969-
dc.identifier.epage981-

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