Synthesis and characterization of new zinc phthalocyanine compounds with octa substituted morpholine groups

Phthalocyanine compounds used as photosensitizers in photodynamic therapy show promising results on cancer cells and are of great importance in studies conducted in this field. Morpholine compound, which exhibits advantageous properties such as being anti-inflammatory and antimicrobial, also has easy synthesis methods. It is thought that phthalocyanine compounds with morpholine groups attached can be used as anticancer agents. Click chemistry is of great importance in bioconjugation, drug and polymer chemistry. The biological activities of phthalocyanines containing triazole rings synthesized as a result of copper-catalyzed azide-alkyne cycloaddition have gained importance in terms of medical applications and the studies conducted are increasing. In this thesis study, phthalocyanine compounds with octasubstituted morpholine groups attached were synthesized. As a result of the reaction of 4,5-bis((2-iodoethyl)thio)phthalonitrile compound and morpholine compound in dry DMF solution, 4,5-bis((2-morpholinoethyl)thio)phthalonitrile compound was obtained. The obtained compound was reacted with zinc acetate in the presence of DBU and zinc phthalocyanine compound was synthesized. In the zinc phthalocyanine compound containing triazole ring, firstly ((4,5-dicyano-1,2-phenylene)bis(sulfanedyl))bis(ethane-2,1-dyl)bis(4-methylbenzenesulfonate) compound was reacted with NaN3 in dry acetonitrile. As a result of this reaction, 4,5-bis((2-azidoethyl)thio)phthalonitrile compound was obtained. Then, CuAAC click reaction was carried out in dry tert-butanol using this compound and 4-(prop-2-yn-1-yl)morpholine compound. Zinc phthalocyanine compound was synthesized from the synthesized triazole ring phthalonitrile compound. Finally, these synthesized zinc phthalocyanine compounds were made water soluble using methyliodide for in vitro and in vivo studies. The structures of each synthesized substance were elucidated and characterized using FT-IR and mass spectrometers, 1H NMR and 13C NMR, UV‒vis spectrophotometer.