Synthesis of porphyrazine-octaamine, hexamine and diamine derivatives

The syntheses of a variety of substituted diaminomaleonitriles, with variable nitrogen substituents, were undertaken. Linstead macrocyclization of the resulting diaminomaleonitriles gave access to a wide range of functionalized porphyrazine-octaamines and hexamines and norphthalocyaninediamines. Conversion of these macrocycles into metallic derivatives and studies of their electronic absorption, solubility and electrochemistry are described. These flexible tetraazaporphyrins show potential in a range of applications including biomedical agents, novel charge–transfer complexes, chemical sensors, novel electronic materials and non-linear optics.