On the Reaction of Naphthalene Diimides with Fluoride Ions: Acid/Base versus Redox Reactions.

The characterization of a naphthalene diimide (NDI) radical anion is presented. Its properties allow a reliable comparison point for other systems involving the NDI radical anion, such as systems claimed to perform the oxidation of the fluoride anion. In addition to reiterating the obvious thermodynamic objections to such an unlikely oxidation, we present several observations that show that the fluoride anion does not act as a one-electron reducing agent toward the NDI investigated in this work.