Radical Anions of trifluoromethylated perylene and naphthalene imide and diimide electron acceptors

Vladimir V. Roznyatovskiy, Daniel M. Gardner, Samuel W. Eaton, Michael R Wasielewski*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

51 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)696-699
Number of pages4
JournalOrganic Letters
Volume16
Issue number3
DOIs
StatePublished - Feb 7 2014

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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