Synthesis and characterization of novel type of phthalocyanines containing naphtyl chalcone groups on peripheral positions

In this study, starting from 1-naphtyl chalcone compound some novel metallo and metal-free phthalocyanine compounds were synthesized and their structures were characterized by spectroscopic methods. In this thesis, firstly 1-naphtyl chalcone compound (3) was synthesized from the reaction of 1-naphtaldehyde and 4-hydroxyacetophenone using the Claisen–Schmidt base-catalyzed aldol condensation according to the literature. 4-(1-Naphtyl chalcone) substitue phtalonitrile compound (5) was obtained from the nucleophilic aromatic substitution reaction of synthesized 1-naphthyl chalcone (3) and 4-nitrophthalonitrile in the presence of K2CO3 in dry DMF at 70 oC under nitrogen atmosphere. In the second part of this thesis, periferal tetrasubstituted metallo-phthalocyanine complexes (6-9) were synthesized by 'heating of solid phase' method. By using this technique, the cyclotetramerization of 4-(1-naphthyl chalcone) substitue phthalonitrile compound (5) with corresponding metal salts (Co(II), Zn(II), Ni(II) and Cu(II) acetates) under nitrogen atmosphere resulted with the formation of novel metallo-phthalocyanines (6-9). Metal-free phtalocyanine compound (10) was also obtained from the cyclotetramerization reaction of 4-(1-naphthyl chalcone) substitue phthalonitrile (5) at the same conditions using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as basic catalyst. The structures of the synthesized novel compounds were confirmed by using UV-Visible, FT-IR, 1H and 13C-NMR, and mass spectroscopic technices. Key Words: Naphthyl Chalcone, Phthalocyanine, CoPc, ZnPc, NiPc, CuPc