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

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

Research output: Contribution to journalArticle

35 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 languageEnglish
Pages (from-to)696-699
Number of pages4
JournalOrganic Letters
Volume16
Issue number3
DOIs
Publication statusPublished - Feb 7 2014

Fingerprint

Perylene
Imides
imides
naphthalene
Anions
Electrons
anions
X ray analysis
Paramagnetic resonance
Spectrum Analysis
electrons
X-Rays
Single crystals
Spectroscopy
single crystals
spectroscopy
x rays
naphthalenediimide

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 journalArticle

Roznyatovskiy, Vladimir V. ; Gardner, Daniel M. ; Eaton, Samuel W. ; Wasielewski, Michael R. / Radical Anions of trifluoromethylated perylene and naphthalene imide and diimide electron acceptors. In: Organic Letters. 2014 ; Vol. 16, No. 3. pp. 696-699.
@article{cfc98b6f0a1143bb8cdb404b387c227a,
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.",
author = "Roznyatovskiy, {Vladimir V.} and Gardner, {Daniel M.} and Eaton, {Samuel W.} and Wasielewski, {Michael R}",
year = "2014",
month = "2",
day = "7",
doi = "10.1021/ol403736m",
language = "English",
volume = "16",
pages = "696--699",
journal = "Organic Letters",
issn = "1523-7060",
publisher = "American Chemical Society",
number = "3",

}

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

UR - http://www.scopus.com/inward/citedby.url?scp=84893838986&partnerID=8YFLogxK

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 -