4,8,12,16-Tetra-tert-butyl-s-indaceno[1,2,3-cd:5,6,7-c‘d‘]diphenalene: A Four-Stage Amphoteric Redox System
Journal of the American Chemical Society1998Vol. 120(9), pp. 2018–2027
Citations Over TimeTop 20% of 1998 papers
Kenji Ohashi, Takashi Kubo, Takashi Masui, Kagetoshi Yamamoto, Kazuhiro Nakasuji, Takeji Takui, Yasushi Kai, Ichiro Murata
Abstract
A four-stage amphoteric redox hydrocarbon (5) containing two phenalenyl units was prepared. X-ray crystallography of 5 reveals a delocalized D2h structure, which is consistent with the presence of only five signals in the 1H NMR spectrum of 5 at −60 °C. The cyclic voltammogram of 5 exhibits four reversible redox waves with a small numerical sum (E1sum) of first oxidation (E1ox) and reduction (E1red) potentials. Four redox states of 5 were successfully generated from the neutral 5 and were characterized by NMR, ESR, and UV−vis−near-IR spectroscopies and theoretical calculations. These spectral data reveal that phenalenyl units play an important role in the high amphotericity of 5 and the stability of the redox states generated.
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