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Electrochemistry, Spectroscopy And Electrogenerated Chemiluminescence Of Perylene, Terrylene, And Quaterrylene Diimides In Aprotic Solution

S. Lee, Y. Zu, A. Herrmann, Y. Geerts, K. Müllen, A. J. Bard
Published 1999 · Chemistry

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The electrochemistry, UV−vis spectrophotometry, photoluminescence, and electrogenerated chemiluminescence (ECL) of perylenedicarboxylic imide, perylenetetracarboxylic diimide (PDI), terrylenetetracarboxylic diimide (TDI), and quaterrylenecarboxylic diimide (QDI) were investigated. All compounds undergo two reversible one-electron reductions and one reversible one-electron oxidation reaction. The first reduction potential shifts to less negative values and the potential for oxidation to less positive values for the diimide series with increasing size of the aromatic core. These changes in potential correlate well with orbital energies from molecular orbital calculations. The difference in potential between the first and second reduction waves decreased with increasing distance between the imide groups, so that TDI and QDI show only a single reduction wave, equivalent to a two-electron reduction. These reduction potentials provide estimates for the equilibrium constant for disproportionation of the radical ...
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