Synthesis and Characterization of Several Series of Substituted Metallophthalocyanines

The twenty-four substituted metallophthalocyanines were synthesized, in two steps, from 4-nitrophthalonitrile or 3-nitrophthalonitrile, and characterized by MS, ¹H NMR, UV-vis, IR and element analysis. The results showed that they all were consistent with proposed structures. They behaved excellent solubility in some organic solvents, but the stability of them in solution was not good as in solid state. According to the scopes of red shift, the impact of metals, substituents and substitution positions on Q-bands could be displayed as follow: Mn > Zn ≈ Cu > Ni ≈ Co; 2-isopropyl-5-methylphenoxyl ≥ 4-tert-butylphenoxyl ≥ quinolin-8-yloxyl ≥ 2-methoxyethoxyl; non-periphery > periphery. The research displayed that the alternative ways to control the Q bands of Pc compounds to have a big change were to alter the chemical value of metal in the center of Pc ring, replace the atom banding directly with Pc ring or its chemical circumstance, and change the substitution position of substituent on Pc ring (periphery or non-periphery).