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One-Electron Reduction of an “Extended Viologen” p-Phenylene-bis-4,4‘-(1-aryl-2,6-diphenylpyridinium) Dication

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Alison Funston,^† James P. Kirby,^† John R. Miller,^† Lubomír Pospíšil,^‡ Jan Fiedler,^‡ Magdaléna Hromadová,^‡ Miroslav Gál,^‡ Jaroslav Pecka,^§ Michal Valášek,^§ Zbigniew Zawada,^‖ Pawel Rempala,^‖ and Josef Michl*^‖

Chemistry Department, Brookhaven National Laboratory, Building 555A, Upton, New York 11973, J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, Dolejškova 3, 18223 Prague, Department of Organic Chemistry, Charles University, Albertov 2030, Prague, Czech Republic, and Department of Chemistry and Biochemistry, University of Colorado, Boulder, Colorado 80309-0215

J. Phys. Chem. A, 2005, 109 (48), pp 10862–10869

DOI: 10.1021/jp053556n

Publication Date (Web): November 10, 2005

Section:

Physical Organic Chemistry

Abstract

One-electron reduction of the “extended viologen” dication 1 yields the red cation radical 2, characterized by strong near-IR absorption. It has been generated and studied by pulse radiolytic, electrochemical, redox titration, UV−visible, and electron paramagnetic resonance spectroscopic methods. All results are in agreement with a fully delocalized electronic structure for 2.

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This article has been cited by 4 ACS Journal articles (4 most recent appear below).

Single-Step versus Stepwise Two-Electron Reduction of Polyarylpyridiniums: Insights from the Steric Switching of Redox Potential Compression
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Journal of the American Chemical Society2012 134 (5), 2691-2705
- Single-Step versus Stepwise Two-Electron Reduction of Polyarylpyridiniums: Insights from the Steric Switching of Redox Potential Compression
  Jérôme Fortage, Cyril Peltier, Christian Perruchot, Yohei Takemoto, Yoshio Teki, Fethi Bedioui, Valérie Marvaud, Grégory Dupeyre, Lubomír Pospísil, Carlo Adamo, Magdaléna Hromadová, Ilaria Ciofini, and Philippe P. Lainé
  Journal of the American Chemical Society2012 134 (5), 2691-2705
  Contrary to 4,4′-dipyridinium (i.e., archetypal methyl viologen), which is reduced by two single-electron transfers (stepwise reduction), the 4,1′-dipyridinium isomer (so-called “head-to-tail” isomer) undergoes two electron transfers at apparently the ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Photoswitchable Organic Mixed Valence in Dithienylcyclopentene Systems with Tertiary Amine Redox Centers
Bice He and Oliver S. Wenger
Journal of the American Chemical Society2011 133 (42), 17027-17036
- Photoswitchable Organic Mixed Valence in Dithienylcyclopentene Systems with Tertiary Amine Redox Centers
  Bice He and Oliver S. Wenger
  Journal of the American Chemical Society2011 133 (42), 17027-17036
  The electronic structures of the radical cations of two dithienylperfluorocyclopentene molecules with appended tertiary amine units were investigated by electrochemical and optical spectroscopic methods. The through-bond N–N distances in the photocyclized ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Organic Mixed Valence
Jihane Hankache and Oliver S. Wenger
Chemical Reviews2011 Article ASAP
- Organic Mixed Valence
  Jihane Hankache and Oliver S. Wenger
  Chemical Reviews2011 Article ASAP
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Cobaltocene-Doped Viologen as Functional Components in Organic Electronics
Chang Su Kim, Stephanie Lee, Leonard L. Tinker, Stefan Bernhard and Yueh-Lin Loo
Chemistry of Materials2009 21 (19), 4583-4588
- Cobaltocene-Doped Viologen as Functional Components in Organic Electronics
  Chang Su Kim, Stephanie Lee, Leonard L. Tinker, Stefan Bernhard and Yueh-Lin Loo
  Chemistry of Materials2009 21 (19), 4583-4588
  Given the energy level alignment between viologen and cobaltocene, cobaltocene readily transfers electrons to the intrinsically insulating viologen, resulting in the formation of an electron transfer complex with high electron density. When cobaltocene−...
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