Solid-state characterization and photoinduced intramolecular electron transfer in a nanoconfined octacationic homo[2]catenane

Jonathan C. Barnes, Marco Frasconi, Ryan M. Young, Nezar H. Khdary, Wei Guang Liu, Scott M. Dyar, Paul R. McGonigal, Ian C. Gibbs-Hall, Christian S. Diercks, Amy A. Sarjeant, Charlotte L. Stern, William A. Goddard, Michael R Wasielewski, J. Fraser Stoddart

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

An octacationic homo[2]catenane comprised of two mechanically interlocked cyclobis(paraquat-p-phenylene) rings has been obtained from the oxidation of the septacationic monoradical with nitrosonium hexafluoroantimonate. The nanoconfinement of normally repulsive bipyridinium units results in the enforced π-overlap of eight positively charged pyridinium rings in a volume of 3. In the solid state, the torsional angles around the C-C bonds between the four pairs of pyridinium rings range between 16 and 30°, while the π-π stacking distances between the bipyridinium units are extended for the inside pair and contracted for the pairs on the outside-a consequence of Coulombic repulsion between the inner bipyridinium subunits. In solution, irradiation of the [2]catenane at 275 nm results in electron transfer from one of the paraphenylene rings to the inner bipyridinium dimer, leading to the generation of a temporary mixed-valence state within the rigid and robust homo[2]catenane.

Original languageEnglish
Pages (from-to)10569-10572
Number of pages4
JournalJournal of the American Chemical Society
Volume136
Issue number30
DOIs
Publication statusPublished - Jul 30 2014

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Dimers
Irradiation
Electrons
Oxidation
Paraquat
catenane

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Barnes, J. C., Frasconi, M., Young, R. M., Khdary, N. H., Liu, W. G., Dyar, S. M., ... Stoddart, J. F. (2014). Solid-state characterization and photoinduced intramolecular electron transfer in a nanoconfined octacationic homo[2]catenane. Journal of the American Chemical Society, 136(30), 10569-10572. https://doi.org/10.1021/ja505093d

Solid-state characterization and photoinduced intramolecular electron transfer in a nanoconfined octacationic homo[2]catenane. / Barnes, Jonathan C.; Frasconi, Marco; Young, Ryan M.; Khdary, Nezar H.; Liu, Wei Guang; Dyar, Scott M.; McGonigal, Paul R.; Gibbs-Hall, Ian C.; Diercks, Christian S.; Sarjeant, Amy A.; Stern, Charlotte L.; Goddard, William A.; Wasielewski, Michael R; Stoddart, J. Fraser.

In: Journal of the American Chemical Society, Vol. 136, No. 30, 30.07.2014, p. 10569-10572.

Research output: Contribution to journalArticle

Barnes, JC, Frasconi, M, Young, RM, Khdary, NH, Liu, WG, Dyar, SM, McGonigal, PR, Gibbs-Hall, IC, Diercks, CS, Sarjeant, AA, Stern, CL, Goddard, WA, Wasielewski, MR & Stoddart, JF 2014, 'Solid-state characterization and photoinduced intramolecular electron transfer in a nanoconfined octacationic homo[2]catenane', Journal of the American Chemical Society, vol. 136, no. 30, pp. 10569-10572. https://doi.org/10.1021/ja505093d
Barnes, Jonathan C. ; Frasconi, Marco ; Young, Ryan M. ; Khdary, Nezar H. ; Liu, Wei Guang ; Dyar, Scott M. ; McGonigal, Paul R. ; Gibbs-Hall, Ian C. ; Diercks, Christian S. ; Sarjeant, Amy A. ; Stern, Charlotte L. ; Goddard, William A. ; Wasielewski, Michael R ; Stoddart, J. Fraser. / Solid-state characterization and photoinduced intramolecular electron transfer in a nanoconfined octacationic homo[2]catenane. In: Journal of the American Chemical Society. 2014 ; Vol. 136, No. 30. pp. 10569-10572.
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