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 language | English |
|---|---|
| Pages (from-to) | 696-699 |
| Number of pages | 4 |
| Journal | Organic Letters |
| Volume | 16 |
| Issue number | 3 |
| DOIs | |
| Publication status | Published - Feb 7 2014 |
ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
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Roznyatovskiy, V. V., Gardner, D. M., Eaton, S. W., & Wasielewski, M. R. (2014). Radical Anions of trifluoromethylated perylene and naphthalene imide and diimide electron acceptors. Organic Letters, 16(3), 696-699. https://doi.org/10.1021/ol403736m