Synthesis and characterization of dendritic phthalocyanines containing large steric effect groups

Phthalocyanines are used in catalytic reactions, gas sensors, solar cells, liquid crystals and photodynamic cancer treatment because of their optical, chemical and physical properties. Phthalocyanine and dendritic phthalocyanine derivatives containing large groups of steric effect appear to be used in homogeneous catalytic reactions, particularly in selective catalytic oxidation reactions. For these reasons, the synthesis and characterization of dendritic phthalocyanin containing electron donor groups and large groups of steric effect will be important. In this study, dendritic phthalocyanines were prepared in which p-tertiary butylphenoxy groups having large the steric effect and electron donor properties were bound to tris derivated. The reaction of tris(hydroxymethyl)nitromethane with thionyl chloride in pyridine gave the tris(chloromethyl)nitromethane, which was reduced by Pd / C to give tris(chloromethyl)aminomethane. The dendritic group 3 was prepared by the reaction of phenoxy salt (which obtained by reaction of NaH and p-tert-butylphenol) and tris(chloromethyl)aminomethane in THF. At room temperature, the reaction of 3 and 4,5-dichlorophthalonitrile in the presence of K2CO3 in DMF was used to prepare compound 4. The tetramerisation of the compound 4 and Li metal in pentanol was prepared and the lithium phthalocyanine derivative, and the metal-free dendritic phthalocyanine 5 was synthesized by hydrolysis of this compound with concentrated H2SO4. In DMF the presence of DBU, the reaction of 4 compounds with Zn(OAc)2 and Co(OAc)2 resulted in the preparation of dendritic zinc phthalocyanine derivative 6 and dendritic cobalt phthalocyanine derivative 7 respectively. All phthalocyanine derivatives are soluble in organic solvents such as ether, CHCl3, acetone. The prepared compounds were characterized by 1H-NMR, 13C-NMR,UV-vis and IR spectroscopic methods.