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 |
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ASJC Scopus subject areas
- Organic Chemistry
- Physical and Theoretical Chemistry
- Biochemistry
Cite this
Radical Anions of trifluoromethylated perylene and naphthalene imide and diimide electron acceptors. / Roznyatovskiy, Vladimir V.; Gardner, Daniel M.; Eaton, Samuel W.; Wasielewski, Michael R.
In: Organic Letters, Vol. 16, No. 3, 07.02.2014, p. 696-699.Research output: Contribution to journal › Article
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TY - JOUR
T1 - Radical Anions of trifluoromethylated perylene and naphthalene imide and diimide electron acceptors
AU - Roznyatovskiy, Vladimir V.
AU - Gardner, Daniel M.
AU - Eaton, Samuel W.
AU - Wasielewski, Michael R
PY - 2014/2/7
Y1 - 2014/2/7
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84893838986&partnerID=8YFLogxK
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U2 - 10.1021/ol403736m
DO - 10.1021/ol403736m
M3 - Article
VL - 16
SP - 696
EP - 699
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 3
ER -