Ethynylferrocenyl derivatives of 2,7-acridine (1, 2), 9-N-acridone (4), and 2-anthraquinone
(6) are described. (Z)-10-(2-iodo-1-ethenylferrocene)-9(10H)-acridinone (3), an intermediate
in the formation of 4, N-Fc(CH2)
n
-acridone (5; n = 8, 11), 1-Fc-anthraquinone (7), and (E)-(2-FcCC)-anthraquinone (8) were also investigated. The X-ray structures of 3 and 6 were
determined. B3LYP calculations, UV/vis spectroelectrochemistry, cyclic voltammetry, and
ESR spectra were used to probe the ground and excited states of both the neutral and oxidized
compounds. Emission is observed from oxidized, but not neutral, 4 and 6; however, 1, 2,
and 8 are fluorescent. Surprisingly, emission is reduced upon oxidation of 2 and 8, which
appears to correlate with the greater distortion in the excited compared to ground states.
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