File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Self-assembly of functionalized [2]catenanes bearing a reactive functional group on either one or both macrocyclic components - From monomeric [2]catenanes to polycatenanes

TitleSelf-assembly of functionalized [2]catenanes bearing a reactive functional group on either one or both macrocyclic components - From monomeric [2]catenanes to polycatenanes
Authors
Issue Date1998
Citation
Macromolecules, 1998, v. 31, n. 2, p. 295-307 How to Cite?
AbstractA series of mono- and difunctionalized [2]catenanes, incorporating a bipyridinium-based cyclophane component interlocked with a dioxyarene-based macrocyclic polyether, have been self-assembled. The methodology relies upon the complementarity between the π-electron-deficient and the π-electron-rich macrocyclic components. Hydrogen-bonding interactions between the acidic hydrogen atoms on the bipyridinium units and the polyether oxygen atoms, as well as π-π stacking and edge-to-face T-type interactions between the complementary aromatic units, are responsible for these self-assembly processes. These [2]catenanes have been designed in order to locate one reactive functional group-either a hydroxyl group or a carboxylic acid function - onto one or both macrocyclic components. In principle, polymerization or copolymerization of these monomeric [2]catenanes can be realized by condensations at the reactive functional groups to generate main-chain, side-chain, and dendritic polycatenanes. Indeed, the versatility of this design logic has been demonstrated by some preliminary experiments. A main-chain oligo[2]catenane incorporating 17 repeating units connected by urethane linkages was synthesized by the condensation of a monomeric difunctionalized [2]catenane bearing one hydroxymethyl group on each of its two macrocyclic components with a diisocyanate derivative. The geometries adopted in the solid state by some of the monomeric [2]catenanes were examined by single-crystal X-ray analyses. Interestingly, in the case of a monofunctionalized [2Jcatenane bearing one carboxylic acid group on its π-electron-rich macrocyclic component, pseudobis[2]catenanes are observed in the solid state as a result of the formation of hydrogen-bonded dimers between the carboxylic acid groups of adjacent molecules.
Persistent Identifierhttp://hdl.handle.net/10722/332420
ISSN
2023 Impact Factor: 5.1
2023 SCImago Journal Rankings: 1.401
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorMenzer, Stephan-
dc.contributor.authorWhite, Andrew J.P.-
dc.contributor.authorWilliams, David J.-
dc.contributor.authorBělohradský, Martin-
dc.contributor.authorHamers, Christoph-
dc.contributor.authorRaymo, Francisco M.-
dc.contributor.authorShipway, Andrew N.-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-10-06T05:11:20Z-
dc.date.available2023-10-06T05:11:20Z-
dc.date.issued1998-
dc.identifier.citationMacromolecules, 1998, v. 31, n. 2, p. 295-307-
dc.identifier.issn0024-9297-
dc.identifier.urihttp://hdl.handle.net/10722/332420-
dc.description.abstractA series of mono- and difunctionalized [2]catenanes, incorporating a bipyridinium-based cyclophane component interlocked with a dioxyarene-based macrocyclic polyether, have been self-assembled. The methodology relies upon the complementarity between the π-electron-deficient and the π-electron-rich macrocyclic components. Hydrogen-bonding interactions between the acidic hydrogen atoms on the bipyridinium units and the polyether oxygen atoms, as well as π-π stacking and edge-to-face T-type interactions between the complementary aromatic units, are responsible for these self-assembly processes. These [2]catenanes have been designed in order to locate one reactive functional group-either a hydroxyl group or a carboxylic acid function - onto one or both macrocyclic components. In principle, polymerization or copolymerization of these monomeric [2]catenanes can be realized by condensations at the reactive functional groups to generate main-chain, side-chain, and dendritic polycatenanes. Indeed, the versatility of this design logic has been demonstrated by some preliminary experiments. A main-chain oligo[2]catenane incorporating 17 repeating units connected by urethane linkages was synthesized by the condensation of a monomeric difunctionalized [2]catenane bearing one hydroxymethyl group on each of its two macrocyclic components with a diisocyanate derivative. The geometries adopted in the solid state by some of the monomeric [2]catenanes were examined by single-crystal X-ray analyses. Interestingly, in the case of a monofunctionalized [2Jcatenane bearing one carboxylic acid group on its π-electron-rich macrocyclic component, pseudobis[2]catenanes are observed in the solid state as a result of the formation of hydrogen-bonded dimers between the carboxylic acid groups of adjacent molecules.-
dc.languageeng-
dc.relation.ispartofMacromolecules-
dc.titleSelf-assembly of functionalized [2]catenanes bearing a reactive functional group on either one or both macrocyclic components - From monomeric [2]catenanes to polycatenanes-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/ma970685w-
dc.identifier.scopuseid_2-s2.0-0031647060-
dc.identifier.volume31-
dc.identifier.issue2-
dc.identifier.spage295-
dc.identifier.epage307-
dc.identifier.isiWOS:000071733100010-

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats