The green fluorescence emission of 9-aminoanthracence (
9AA
) was maintained
by controlling the oxidation of
9AA
with oxygen in the
solid state and in solution. The solid-state fluorescence of
9AA
was maintained for a longer time when lauric acid was
used because the equilibrium between
9AA
and 9-anthrylammonium
salt (
9AAH
+
) inclines toward
the right-hand side in the presence of an acid. A solution of
9AA
in CDCl
3
, to which nitrogen had been bubbled
through for 5 min, continued to emit green fluorescence for more than
3 days, whereas the fluorescence emission disappeared within 3 days
for the solution that had been bubbled with oxygen for 5 min.
9AA
is oxidized by oxygen in MeOH under dark conditions to
give almost nongreen fluorescent anthraquinone monoimine (
AQNH
), whereas dimerization of
9AA
occurs under UV irradiation
at 365 nm, much faster than the generation of
AQNH
. These
results suggest that
9AA
is oxidized by the triplet rather
than the singlet oxygen in MeOH. Some of the organic molecules, proteins,
and biological tissues were successfully stained with
9AA
on microscope slides within 10 min because the green fluorescence
emission of
9AA
was successfully maintained in the presence
of an acid and under hypoxic conditions of the used materials.