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  Photophysics and redox properties of rylene imide and diimide dyes alkylated ortho to the imide groups.

Bullock, J. E., Vagnini, M. T., Ramanan, C., Co, D. T., Wilson, T. M., Dicke, J. W., et al. (2010). Photophysics and redox properties of rylene imide and diimide dyes alkylated ortho to the imide groups. The Journal of Physical Chemistry B, 114(5), 1794-1802. doi:10.1021/jp908679c.

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Item Permalink: http://hdl.handle.net/21.11116/0000-0005-49EE-E Version Permalink: http://hdl.handle.net/21.11116/0000-0005-4A1A-C
Genre: Journal Article

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 Creators:
Bullock, Joseph E, Author
Vagnini, Michael T, Author
Ramanan, Charusheela1, Author              
Co, Dick T, Author
Wilson, Thea M, Author
Dicke, Jay W, Author
Marks, Tobin J., Author
Wasielewski, Michael R., Author
Affiliations:
1Department of Chemistry, Argonne-Northwestern Solar Energy Research (ANSER) Center, Northwestern University, Evanston, Illinois, ou_persistent22              

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Free keywords: building-blocks,c-h bonds,carbon-hydrogen bonds,charge separation,crystalline coronene derivatives,energy-transfer,fluorescent dyes,perylene diimides,photoinduced electron-transfer,ruthenium-catalyzed addition
 Abstract: Ruthenium-catalyzed C-H bond activation was used to directly attach phenethyl groups derived from styrene to positions ortho to the imide groups in a variety of rylene imides and diimides including naphthalene-1,8-dicarboximide (NMI), naphthalene-1,4:5,8-bis(dicarboximide) (NI), perylene-3,4-dicarboximide (PMI), perylene-3,4:9, 10-bis(dicarboximide) (PDI), and terrylene-3,4:11,12-bis(dicarboximide) (TDI). The monoimides were dialkylated, while the diimides were tetraalkylated, with the exception of NI, which could only be dialkylated due to steric hindrance. The absorption, fluorescence, transient absorption spectra, and lowest excited singlet state lifetimes of these chromophores, with the exception of NI, are nearly identical to those of their unsubstituted parent chromophores. The reduction potentials of the dialkylated chromophores are similar to 100 mV more negative and oxidation potentials are similar to 40 mV less positive than those of the parent compounds, while the corresponding potentials of the tetraalkylated compounds are similar to 200 mV more negative and similar to 100 mV less positive than those of their parent compounds, respectively. Continuous wave electron paramagnetic resonance (EPR) and electron nuclear double resonance (ENDOR) data on the radical anion of PDI reveals spin density on the perylene-core protons as well as on the beta-protons of the phenethyl groups. The phenethyl groups enhance the otherwise poor solubility of the bis(dicarboximide) chromophores and only weakly perturb the photophysical and redox properties of the parent molecules, rendering these derivatives and related molecules of significant interest to solar energy conversion.

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Language(s): eng - English
 Dates: 20102010
 Publication Status: Published in print
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Method: -
 Identifiers: DOI: 10.1021/jp908679c
 Degree: -

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Title: The Journal of Physical Chemistry B
  Other : J. Phys. Chem. B
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 114 (5) Sequence Number: - Start / End Page: 1794 - 1802 Identifier: ISSN: 1520-6106
CoNE: https://pure.mpg.de/cone/journals/resource/1000000000293370_1