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

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

doi:10.1021/ol403736m

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

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

Northwestern University

Research output: Contribution to journal › Article › peer-review

42 Citations (Scopus)

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	https://doi.org/10.1021/ol403736m
Publication status	Published - Feb 7 2014

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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AU - Roznyatovskiy, Vladimir V.

AU - Gardner, Daniel M.

AU - Eaton, Samuel W.

AU - Wasielewski, Michael R.

PY - 2014/2/7

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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.

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