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.