File Download

There are no files associated with this item.

  Links for fulltext
     (May Require Subscription)
Supplementary

Article: Degenerate [2]rotaxanes with electrostatic barriers

TitleDegenerate [2]rotaxanes with electrostatic barriers
Authors
Issue Date2011
Citation
Organic and Biomolecular Chemistry, 2011, v. 9, n. 7, p. 2240-2250 How to Cite?
AbstractA synthetic approach to the preparation of [2]rotaxanes (1-5·6PF6) incorporating bispyridinium derivatives and two 1,5-dioxynaphthalene (DNP) units situated in the rod portions of their dumbbell components that are encircled by a single cyclobis(paraquat-p-phenylene) tetracationic (CBPQT4+) ring has been developed. Since the π-electron-deficient bispyridinium units are introduced into the dumbbell components of the [2]rotaxanes 1-5·6PF6, there are Coulombic charge-charge repulsions between these dicationic units and the CBPQT 4+ ring in the [2]rotaxanes. Thus, the CBPQT4+ rings in the degenerate [2]rotaxanes exhibit slow shuttling between two DNP recognition sites on the 1H NMR time-scale on account of the electrostatic barrier posed by the bispyridinium units, as demonstrated by variable-temperature 1H NMR spectroscopy. Electrochemical experiments carried out on the [2]rotaxanes 1·6PF6 and 2·6PF 6 indicate that the one-electron reduced bipyridinium radical cation in the dumbbell components of the [2]rotaxanes serves as an additional recognition site for the two-electron reduced CBPQT2(+) diradical cationic ring. Under appropriate conditions, the ring components in the degenerate rotaxanes 1·6PF6 and 2·6PF6 can shuttle along the recognition sites - two DNP units and one-electron reduced bipyridinium radical cation - under redox control. © 2011 The Royal Society of Chemistry.
Persistent Identifierhttp://hdl.handle.net/10722/332940
ISSN
2023 Impact Factor: 2.9
2023 SCImago Journal Rankings: 0.607
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorLi, Hao-
dc.contributor.authorZhao, Yan Li-
dc.contributor.authorFahrenbach, Albert C.-
dc.contributor.authorKim, Soo Young-
dc.contributor.authorPaxton, Walter F.-
dc.contributor.authorStoddart, J. Fraser-
dc.date.accessioned2023-10-06T05:15:31Z-
dc.date.available2023-10-06T05:15:31Z-
dc.date.issued2011-
dc.identifier.citationOrganic and Biomolecular Chemistry, 2011, v. 9, n. 7, p. 2240-2250-
dc.identifier.issn1477-0520-
dc.identifier.urihttp://hdl.handle.net/10722/332940-
dc.description.abstractA synthetic approach to the preparation of [2]rotaxanes (1-5·6PF6) incorporating bispyridinium derivatives and two 1,5-dioxynaphthalene (DNP) units situated in the rod portions of their dumbbell components that are encircled by a single cyclobis(paraquat-p-phenylene) tetracationic (CBPQT4+) ring has been developed. Since the π-electron-deficient bispyridinium units are introduced into the dumbbell components of the [2]rotaxanes 1-5·6PF6, there are Coulombic charge-charge repulsions between these dicationic units and the CBPQT 4+ ring in the [2]rotaxanes. Thus, the CBPQT4+ rings in the degenerate [2]rotaxanes exhibit slow shuttling between two DNP recognition sites on the 1H NMR time-scale on account of the electrostatic barrier posed by the bispyridinium units, as demonstrated by variable-temperature 1H NMR spectroscopy. Electrochemical experiments carried out on the [2]rotaxanes 1·6PF6 and 2·6PF 6 indicate that the one-electron reduced bipyridinium radical cation in the dumbbell components of the [2]rotaxanes serves as an additional recognition site for the two-electron reduced CBPQT2(+) diradical cationic ring. Under appropriate conditions, the ring components in the degenerate rotaxanes 1·6PF6 and 2·6PF6 can shuttle along the recognition sites - two DNP units and one-electron reduced bipyridinium radical cation - under redox control. © 2011 The Royal Society of Chemistry.-
dc.languageeng-
dc.relation.ispartofOrganic and Biomolecular Chemistry-
dc.titleDegenerate [2]rotaxanes with electrostatic barriers-
dc.typeArticle-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1039/c0ob00937g-
dc.identifier.scopuseid_2-s2.0-79952749181-
dc.identifier.volume9-
dc.identifier.issue7-
dc.identifier.spage2240-
dc.identifier.epage2250-
dc.identifier.isiWOS:000288456700028-

Export via OAI-PMH Interface in XML Formats


OR


Export to Other Non-XML Formats