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Four water soluble azo dyes, 4-(isopropyl)-2-[(E)-(4-chlorophenyl)diazenyl]phenol (L1), 4-(isopropyl)-2-[(E)-(2,4-dichlorophenyl)diazenyl]phenol (L2), 4-(sec-butyl)-2-[(E)-(4-chlorophenyl) diazenyl]phenol (L3), 4-(sec-butyl)-2-[(E)-(2,4-dichlorophenyl)diazenyl]phenol (L4), and their Cu(II) and Ni(II) complexes were synthesized and characterized using spectroscopic methods. Examination of their thermal stability revealed similar decomposition temperature of approximately 260–300°C and that they were more thermally stable than their metal complexes. Ni(II) complexes of ligands L2 and L4 were more stable than the other coordination compounds. Among the synthesized ligands, L2 and the complexes Cu(L3)2 and Ni(L4)2 showed both antimicrobial and antifungal activity. However, the other ligands and the complexes were poorly active against selected microorganisms.

Synthesis, thermal stability, electronic features, and antimicrobial activity of phenolic azo dyes and their Ni(II) and Cu(II) complexes