Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 7, Pages 1973-1977Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201309482
Keywords
azo compounds; copper; nanoparticles; aromatic nitro compounds; photocatalysis
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Funding
- SKLCC [2013BWZ006, 2014BWZ006]
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Copper is a low-cost plasmonic metal. Efficient photocatalysts of copper nanoparticles on graphene support are successfully developed for controllably catalyzing the coupling reactions of aromatic nitro compounds to the corresponding azoxy or azo compounds under visible-light irradiation. The coupling of nitrobenzene produces azoxybenzene with a yield of 90% at 60 degrees C, but azobenzene with a yield of 96% at 90 degrees C. When irradiated with natural sunlight (mean light intensity of 0.044Wcm(-2)) at about 35 degrees C, 70% of the nitrobenzene is converted and 57% of the product is azobenzene. The electrons of the copper nanoparticles gain the energy of the incident light through a localized surface plasmon resonance effect and photoexcitation of the bound electrons. The excited energetic electrons at the surface of the copper nanoparticles facilitate the cleavage of the NO bonds in the aromatic nitro compounds. Hence, the catalyzed coupling reaction can proceed under light irradiation and moderate conditions. This study provides a green photocatalytic route for the production of azo compounds and highlights a potential application for graphene.
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