Synthesis of new phthalocyanines from the 4-(4′–phenoxy-3-chlorochalcone) phthalonitrile

In this study, a new type of metallo phthalocyanines containing chalcone groups on the periphery were synthesized starting from 4'-hydroxy-3-chloro chalcone compound and their structures were characterized by spectroscopic methods. In the first stage of study, 4′–phenoxy-3-chloro chalcone compound (1) was synthesized by the Claisen-Schmidt-type base catalyzed condensation reaction of 4-hydroxyacetophenone and 3-chlorobenzaldehyde in the presence of NaOH. Then the new 3-chlorochalcone substituted phthalonitrile derivative (2) was obtained by the nucleophilic aromatic substitution reaction (SNAr) with the synthesized 3-chloro chalcone compound (1) and 4-nitrophthalonitrile in the presence of K2CO3 in dry DMF under nitrogen atmosphere. In the second stage of study, new metallo phthalocyanine complexes containing chalcone groups on the periphery (3-6) were synthesized using "solid-solid heating method" in the presence of 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) as basic catalyst with the 3-chloro chalcone substituted phthalonitrile (2). For this purpose, performed by the cyclization reaction with chalcone substituted phthalonitrile compound (2) under nitrogen atmosphere in the presence of appropriate metal salts (Co(II), Zn(II), Ni(II) and Cu(II) acetates), new metal phthalocyanine compound (3-6) was obtained. The structure of synthesized compounds were elucidated using the spectroscopic methods such as UV-Vis, FT-IR, NMR and Mass spectroscopy.