Synthesis and Properties of Metal Complexes with Halogen-Substituted Octaphenyltetraazaporphyrins

By reactions of di(4-halophenyl)maleindinitriles with magnesium and zinc(II) acetates in boiling ethylene glycol, Mg(II)-octa-(4-chlorophenyl)tetraazaporphyrin, Mg(II)-octa-(4-fluorophenyl)-tetraazaporphyrin, Zn(II)-octa-(4-chlorophenyl)tetraazaporphyrin, and Zn(II)-octa-(4-fluorophenyl)tetraazaporphyrins were synthesized. The cyclomerization of diphenylmaleinitrile with zinc acetate in ethylene glycol resulted in Zn(II)-Octaphenyltetraazaporphyrin. The corresponding Cu(II) and Mn(III)-octaphenyltetraazaporphyrins were synthesized in dimethylformamide using the metal exchange reaction of halogen-substituted magnesium complexes with copper(II) and manganese(II) chlorides. The obtained compounds were identified by electron absorption, IR, and H-1 NMR spectroscopy, and mass spectrometry. The photochemical stability of the synthesized complexes was studied.