Microwave-assisted synthesis and characterization of phthalocyanines substituted with azo compound containing eugenol moiety

The new metallophthalocyanines (Co, Ni, Cu, and Zn) substituted with azo compound containing eugenol moiety are described. Firstly, azo compound (I) containing eugenol moiety was synthesized by treating eugenol with p-hydroxyaniline. Then phthalonitrile compound (1) was synthesized by microwave-assisted synthesis method. The purification of phthalonitrile compound (1) was carried out by column chromatographic separation. Intramolecular hydrogen bonding in the azo compound (I) prevent base-catalyzed nucleophilic aromatic substitution of OH group belongs eugenol. At the last step, metallophthalocyanines (1a, 1b, 1c, and 1d) were synthesized by the microwave irradiation. The microwave-assisted synthesis method reduces reaction times and enhances the yield of the reactions. All phthalocyanine compounds are soluble in DMF and DMSO. The structures were confirmed by elemental analysis, 1H NMR, 13C NMR, UV/Vis, IR and Mass spectra.

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► The new metallophthalocyanines (Co, Ni, Cu, and Zn) substituted with azo compound containing eugenol moiety are described.
► Intramolecular hydrogen bonding in the azo compounds can prevent substitution of OH group.
► The structures were confirmed by elemental analysis, 1H NMR, 13C NMR, UV/Vis, IR and Mass spectra.