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Issue 7, 2011
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Synthesis of azobenzenes: the coloured pieces of molecular materials

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Abstract

Azobenzenes are ubiquitous motifs very important in many areas of science. Azo compounds display crucial properties for important applications, mainly for the chemical industry. Because of their discovery, the main application of aromatic azo compounds has been their use as dyes. These compounds are excellent candidates to function as molecular switches because of their efficient cistransisomerization in the presence of appropriate radiation. The classical methods for the synthesis of azo compounds are the azo coupling reaction (coupling of diazonium salts with activated aromatic compounds), the Mills reaction (reaction between aromatic nitroso derivatives and anilines) and the Wallach reaction (transformation of azoxybenzenes into 4-hydroxy substituted azoderivatives in acid media). More recently, other preparative methods have been reported. This critical review covers the various synthetic methods reported on azo compounds with special emphasis on the more recent ones and their mechanistic aspects (170 references).

Graphical abstract: Synthesis of azobenzenes: the coloured pieces of molecular materials

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Article information


Submitted
16 Nov 2010
First published
16 Mar 2011

Chem. Soc. Rev., 2011,40, 3835-3853
Article type
Critical Review

Synthesis of azobenzenes: the coloured pieces of molecular materials

E. Merino, Chem. Soc. Rev., 2011, 40, 3835
DOI: 10.1039/C0CS00183J

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