Synthesis and spectral properties of zinc and magnesium phthalocyaninates containing diazenylphenoxy groups

Optimum conditions were selected for the preparation of new phenols: azo dyes of various compositions, namely, 2-phenyldiazenyl-4-(2-phenylpropan-2-yl)phenol and (2,6-dibromo)phenyldiazenyl-4-(2-phenylpropan-2-yl)phenol. Nucleophilic substitution with 3- and 4-nitrophthalonitrile was carried out using the synthesized dyes to form 3/4-[2-phenyldiazenyl-4-(2-phenylpropan-2-yl]phenoxy- and 3/4-[2-(2,6-dibromo)-phenyl)diazenyl]-4-(2-phenylpropan-2-yl)phenoxyphthalonitriles. The metal complexes were synthesized by template condensation in a solution of the corresponding phthalonitrile with zinc or magnesium acetate. The compositions and structures of the synthesized compounds were confirmed by mass spectrometry and NMR, IR, and electronic absorption spectroscopy. The spectral and luminescence properties were studied, the yield of singlet oxygen generation of the synthesized phthalocyanines was determined, and the acid-base properties of the synthesized complexes were investigated.