Radical Anions of Trifluoromethylated Perylene and
Naphthalene Imide and Diimide Electron Acceptors
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Abstract
A series
of electron-deficient perylene and naphthalene imides
and diimides (<b>1</b>–<b>4</b>) 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 <b>1</b>–<b>4</b>. 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
