Radical Anions of Trifluoromethylated Perylene and Naphthalene Imide and Diimide Electron Acceptors

A series
of electron-deficient perylene and naphthalene imides
and diimides (1–4) with varying degrees
of trifluoromethylation were synthesized. Single crystal X-ray analysis
afforded detailed structural information, while spectroelectrochemical
and EPR spectroscopy provided characterization of the radical anions
of 1–4. This study reveals that trifluoromethylation
of the imides and diimides makes their one-electron reduction potentials
substantially more positive relative to the unsubstituted counterparts,
while their other properties remain largely unchanged.