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11,11,12,12-Tetracyano-4,5-pyrenoquinodimethanes: air-stable push-pull o-quinodimethanes with S2 fluorescence

Raúl García1, Sandeep More1, Manuel Melle-Franco2

  • 1†POLYMAT, University of the Basque Country UPV/EHU, Avenida de Tolosa 72, E-20018 Donostia-San Sebastian, Spain.

Organic Letters
|November 15, 2014
PubMed

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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para position.