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On the Reaction of Naphthalene Diimides with Fluoride Ions: Acid/Base versus Redox Reactions
Author(s) -
BélangerChabot Guillaume,
Ali Ahmed,
Gabbaï François P.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201705223
Subject(s) - fluoride , chemistry , redox , ion , naphthalene , photochemistry , diimide , base (topology) , inorganic chemistry , organic chemistry , molecule , mathematical analysis , perylene , mathematics
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.