The role of fluoride in anion–π interaction with naphthalene diimide†
Teck Lip Dexter
Tam 
*a
and
Jian Wei
Xu
*a
*a
and
Jian Wei
Xu
*a
Abstract
The role of fluoride in anion–π interaction with naphthalene diimide (NDI) is dependent on the solvent used. Here we show that in polar aprotic solvents like THF which does not contain any acidic protons, fluoride generates hydroxide that complexes with NDI and it is this complex that reduces NDI to NDI˙−.
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