Bis(n-octylamino)perylene-3,4: 9,10-bis(dicarboximide)s and their radical cations: Synthesis, electrochemistry, and ENDOR spectroscopy

Michael J. Ahrens, Michael J. Tauber, Michael R Wasielewski

Research output: Contribution to journalArticle

73 Citations (Scopus)

Abstract

1,6- and 1,7-bis(n-octylamino)perylene-3,4:9,10-bis(dicarboximide) were synthesized by reaction of n-octylamine with the corresponding dibromo compounds. These compounds display intense charge-transfer optical transitions in the visible spectrum (∼550-750 nm) and fluoresce weakly (ΦF <0.06). Cyclic voltammetry reveals that each chromophore undergoes facile and reversible oxidation and reduction. Spectroelectrochemical studies show that the radical cations of these chromophores are stable and show no signs of deprotonation of the secondary amines. Electron paramagnetic resonance (EPR) and electron-nuclear double resonance (ENDOR) studies of the chemically generated radical cations of these chromophores corroborate the spectroelectrochemical data by showing that the radical cations persist for days at room temperature in methylene chloride solution. These experiments and complementary density functional theory (DFT) calculations provide a comprehensive picture of the molecular orbitals, spin density distributions, and geometries of the radical cations. The redox properties and stability of these alkylamino-functionalized perylene compounds make them a valuable addition to the family of robust perylene-based chromophores that can be used to develop new photoactive charge transport materials.

Original languageEnglish
Pages (from-to)2107-2114
Number of pages8
JournalJournal of Organic Chemistry
Volume71
Issue number5
DOIs
Publication statusPublished - Mar 5 2006

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Perylene
Electrochemistry
Chromophores
Cations
Spectroscopy
Electrons
Charge transfer
Deprotonation
Optical transitions
Methylene Chloride
Molecular orbitals
Cyclic voltammetry
Amines
Density functional theory
Paramagnetic resonance
Oxidation
Geometry
Experiments
Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Bis(n-octylamino)perylene-3,4 : 9,10-bis(dicarboximide)s and their radical cations: Synthesis, electrochemistry, and ENDOR spectroscopy. / Ahrens, Michael J.; Tauber, Michael J.; Wasielewski, Michael R.

In: Journal of Organic Chemistry, Vol. 71, No. 5, 05.03.2006, p. 2107-2114.

Research output: Contribution to journalArticle

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