Synthesis and characterization of carboxyl and tert-Buthyl substueted dendritic assymetric phthalocyanines

Phthalocyanines are one of the class of macrocyclic compounds widely used in scientific studies and advanced technological applications. Thuse of phthalocyanines as photodynamic cancer therapy, solar cells, optical data collection and catalyst is becoming more and more important. Significant results will be obtained by the preparation and characterization of electron-donor tert-butylphenoxy and electron-attractive carboxyl-substituted dendritic asymmetric phthalocyanine derivatives. Because of their catalytic, photophysical and photochemical properties, new compounds will have the potential to be used in different areas, especially in solar cell construction. Reaction of 4,5-difluoro phtalonitrile and dimethyl-5-hydroxyisophthalate in DMSO in the presence of K2CO3 yielded compound 1. In the presence of K2CO3 in DMSO, the reaction of 4,5-dichloro-phthalonitrile with p-chlorophenol yielded the compound 2. Dendritic phthalonitrile derivative 3 was prepared by interaction of this compound with p-tert-butylphenol at room temperature. The lithium phthalocyanine derivative was prepared by reaction of the compound 1 and 3 with Li metal, and hydrolysis of the compound with concentrated HOAc yielded metal-free dendritic phthalocyanine 4. The reaction of compound 1 and 3 with Zn(OAc)2 and [RuCl2(DMSO)4] in DMF and in the presence of DBU resulted in the synthesis of dendritic zinc phthalocyanine derivative 5 and dendritic ruthenium phthalocyanine derivative 6, respectively. Prepared phthalocyanines are dissolved in CHCl3, acetone. The synthesized compounds were characterized by 1H-NMR, 13C-NMR UV-vis and IR spectroscopy methods.