Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 5, Pages 2090-2106Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405157
Keywords
dimerization; electrochemistry; molecular devices; pi interactions; radical ions
Categories
Funding
- Agence National de la Recherche [ANR-12-BS07-0014-01]
- Institut de Chimie de Lyon (ICL, NitroFer project)
- Region Rhone-Alpes
- Labex Arcane [ANR-11-LABX-0003-01]
- IDRIS [i2014086670]
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We have established that bipyridinium radicals can be reversibly pi-dimerized under the combined effects of chemical (proton transfer) and electrochemical (electron transfer) stimuli. Our investigations also led to the discovery that a bis-pyridinyl appended calixarene intermediate is involved in a fully reversible redox-triggered sigma-dimerization process. The structure of the most stable intramolecular sigma-dimer was provided by computational chemistry and its complete conversion into a noncovalent pi-dimer could be triggered chemically by addition of protons, leading to the formation of protonated cation radicals. Theoretical data collected with the N-methylated and N-protonated pi-dimers also support the existence of multivariant orientations in pi-bonded dimers of viologen cation-radicals.
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