Substituted Co(II) and Cu(II) metallophthalocyanines from new Schiff base containing pyrrole units: Synthesis, characterization and investigation of photocatalytic activity on 2,3-dichlorophenol oxidation

Abstract

In this article, novel Schiff base compound 1 bearing pyrrole moiety has been synthesized from the reaction of 1-hydroxybenzaldehyde with 1,2-aminophenylpyrrole for the first time. The cobalt phthalocyanine and copper phthalocyanine (3–4) were prepared by the cyclotetramerization of the novel phthalonitrile compound 2 and the corresponding metal salts. The new phthalonitrile compound 2 was synthesized by the reaction between 4-((E)-{[2-(1H-pyrro-1-yl)phenyl]imino}methyl)phenol 1 and 4-nitrophthalonitrile in DMF. The all new compounds (1–4) have been characterized by FT-IR spectroscopy, 1H-NMR/13C-NMR, mass, UV–Vis spectroscopy techniques and elemental analysis (for metallophthalocyanines). Chlorine-bearing phenols are of a class of pollutants. They have been regarded as a potential risk to environment and human health. It is important to advanced effective techniques to remove chlorinated phenols in wastewater. For this purpose, we investigated that different parameters influenced the photooxidation process were determined and 2,3-dichlorophenol oxidize to the less harmfull products with high conversion and yield in the presence of Cu(II) and Co(II) phthalocyanine catalysts.