Synthesis and Separation of Structural Isomers of 2(3),9(10),16(17),23(24)-Tetrasubstituted Phthalocyanines

The 2(3),9(10),16(17),23(24)-tetrasubstituted metalphthalocyanines 1-7 (M = In, Ni, Zn) were synthesized, as mixtures of four different structural isomers, from the corresponding 4-alkoxy-1,2-dicyanobenzenes and the appropriate metal salts. Separation of the four structural isomers was successfully achieved on a C30 alkyl phase by high-performance liquid chromatography (HPLC). The determination of the point groups of the structural isomers was carried out for 1 and 3, the composition of the structural isomers of 4-7 was accomplished by comparing their retention times and UV/Vis spectra with the data of 1 and 3. For the phthalocyanines 8-10 and the naphthalocyanines 11 and 12 only the C4h and D2h isomers could be separated.