The synthesis, characterization of the new phthalocyanine compounds and investigation of their photodynamic theraphy, thin film properties

In this work, 17,18-dibromo-8-methyl-4,12-ditosyl-3,4,5,6,7,8,9,10,11,12,13,14-dodecahydro-2H-benzo[b][1,4,7,11,15]dioxatriazacycloheptadecine compound (1)was synthesized using N,N'-(3,3'-(methylazanediyl)bis(propane-3,1-diyl))bis(4-methylbenzenesulfon amide) and 1,2-bis(2-iodoethoxy)-4,5-dibromobenzene as starting compounds. This macrocyclic dibromo derivative (1) was treated excess amount of CuCN to get macrocyclic dinitrile derivative (2). Zinc (II) phthalocyanine (3), nickel (II) phthalocyanine (4), cobalt (II) phthalocyanine (5) was synthesized using dinitrile compound (2) with n-pentanol, DBU and dry Zn(CH3COO)2, NiCl2, CoCl2, salts respectively. In addition to this, 4-phenethoxyphthalonitrile compound (6)was synthesized using 2-phenylethanol and 4-nitrophthalonitrile as starting compounds. The metal-free phthalocyanine (7) was synthesized using dinitrile compound (6) with n-pentanol, DBU. Zinc (II) phthalocyanine (8), cobalt (II) phthalocyanine (9), copper (II) phthalocyanine (10) compounds were synthesized by the reaction of dinitrile compound (6) in the presence of dimethylaminoethanol and DBU using dry Zn(CH3COO)2, CoCl2, CuCl2 salts, respectively in microwave oven. Beside this, PDT properties of zinc (II) phthalocyanine (8) was investigated. In addition, thin film properties of metal-free phthalocyanine (7), zinc (II) phthalocyanine (8), cobalt (II) phthalocyanine (9), copper (II) phthalocyanine (10) compounds were investigated. Microscope glasses (Isolab) were used as the substrates. After cleaning the substrates, metal-free phthalocyanine (7), zinc (II) phthalocyanine (8), cobalt (II) phthalocyanine (9), copper (II) phthalocyanine (10) thin films were performed by spin coating method. After then, thermal stability of synthesized phthalocyanines (7), (8), (9), (10) were determined by thermogravimetric analysis (TG/DTA). The structures of the synthesized original compounds were identified by using elemental analysis, IR, 13C-NMR, 1H-NMR, UV-Vis and MS spectral data.