Synthesis and investigation of some properties of new type of phthalocyanines containing 4-coumarinoxy groups in peripheral positions

In this study, it was aimed to synthesize and characterize symmetrical phthalocyanines substituted with coumarin moiety in peripheral positions. The novel phthalocyanines bearing coumarin moiety were prepared in two steps. In the first step, the starting compound 3 (7-(3,4-dicyanophenoxy)-3-chloro-4-methylcoumarin) was synthesized according to the literature method, by using the nucleophilic aromatic displacement reaction between 3-chloro-4-methyl-7-hydroxycoumarin and 4-nitrophthalonitrile in dry dimethylformamide (DMF) in the presence of dry K2CO3. In the second step, the new metallo phthalocyanines (ZnPc, NiPc, CoPc, and CuPc) were prepared by the standart method of cyclotetramerization of corresponding 7-(3,4-dicyanophenoxy)-3-chloro-4-methylcoumarin in the presence of DBU as basic catalysts in DMF for 24 h. In addition it was used the `heating of the solid phase?method for the synthesis of metal free phthalocyanine. Metal free Pc was prepared by heating compound 3 with DBU in a N2 atmosphere in a sealed tube.The structures of the newly synthesized Pcs have been confirmed and characterized by UV/Vis, FT-IR, 1H and 13C NMR spectroscopies and thermal analysis studies.