A four-stage amphoteric redox hydrocarbon
(5) containing two phenalenyl units was prepared.
X-ray
crystallography of 5 reveals a delocalized
D
2
h
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
(E
1
sum) of first oxidation
(E
1
ox) and reduction
(E
1
red) 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.
Ab initio MO calculations were carried out for diradical, polyradical and cation-radical states of azomethyne-ylide dimer and clusters. The calculated results were applied to a molecular design of possible organic analogues to copper-oxide chains and planes in YBa2Cu3O
x
and related species. These organic analogues have molecular skeletons similar to those of conducting polymers and graphite, although their electronic structures are quite different because of electron and spin correlations.
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