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Issue 37, 2012
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A DFT study on photoinduced surface catalytic coupling reactions on nanostructured silver: selective formation of azobenzene derivatives from para-substituted nitrobenzene and aniline

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Abstract

We propose that aromatic nitro and amine compounds undergo photochemical reductive and oxidative coupling, respectively, to specifically produce azobenzene derivatives which exhibit characteristic Raman signals related to the azo group. A photoinduced charge transfer model is presented to explain the transformations observed in para-substituted ArNO2 and ArNH2 on nanostructured silver due to the surface plasmon resonance effect. Theoretical calculations show that the initial reaction takes place through excitation of an electron from the filled level of silver to the lowest unoccupied molecular orbital (LUMO) of an adsorbed ArNO2 molecule, and from the highest occupied molecular orbital (HOMO) of an adsorbed ArNH2 molecule to the unoccupied level of silver, during irradiation with visible light. The para-substituted ArNO2˙ and ArNH2+˙ surface species react further to produce the azobenzene derivatives. Our results may provide a new strategy for the syntheses of aromatic azo dyes from aromatic nitro and amine compounds based on the use of nanostructured silver as a catalyst.

Graphical abstract: A DFT study on photoinduced surface catalytic coupling reactions on nanostructured silver: selective formation of azobenzene derivatives from para-substituted nitrobenzene and aniline

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Publication details

The article was received on 10 May 2012, accepted on 30 Jul 2012 and first published on 30 Jul 2012


Article type: Paper
DOI: 10.1039/C2CP41502J
Phys. Chem. Chem. Phys., 2012,14, 12919-12929

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    A DFT study on photoinduced surface catalytic coupling reactions on nanostructured silver: selective formation of azobenzene derivatives from para-substituted nitrobenzene and aniline

    L. Zhao, Y. Huang, X. Liu, J. R. Anema, D. Wu, B. Ren and Z. Tian, Phys. Chem. Chem. Phys., 2012, 14, 12919
    DOI: 10.1039/C2CP41502J

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