title: Radical anions of trifluoromethylated perylene and naphthalene imide and diimide electron acceptors.
abstract: 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.
authors.affiliation: Department of Chemistry and Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University , Evanston, Illinois 60208-3113, United States.
authors.forename: Vladimir V
authors.initials: VV
authors.lastname: Roznyatovskiy
authors.forename: Daniel M
authors.initials: DM
authors.lastname: Gardner
authors.forename: Samuel W
authors.initials: SW
authors.lastname: Eaton
authors.forename: Michael R
authors.initials: MR
authors.lastname: Wasielewski