Synthesis and characterization of novel 2-{[2-(dimethylamino)ethyl](methyl)amino} ethoxy-substituted metallophthalocyanines

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1. 2, 9(10), 16(17), 23(24)-Tetrakis-(2-{[2-(dimethylamino)ethyl](methyl) amino} ethoxy) ph- thalocyaninato(chloro) - manganese (II) (7) Compound 3 (0.1 g, 0.37 mmol), anhydrous MnCl2(0.013 g, 0.10 mmol), and 2-dimethylaminoethanol (0.5 mL) were irradiated in a microwave oven at 140 ◦: 3055 (C-H, aromatic), 2938–2876 (C-H, aliphatic), 1259 (C-O-C). Analysis of C60H80ClMnN16O4(1179.77) (% calcd./found): C: 61.08/61.70, H: 6.83/6.78, N: 19.00/18.95. 2, 9(10), 16(17), 23(24)-Tetrakis-(2-{[2-( trimethylamino)ethyl] (dimethyl)amino} ethoxy) phthalocyaninatozinc(II) octaiodide (8) Compound 4 (0.206 g, 0.37 mmol), anhydrous Zn(CH3COO)2(0.018 g, 0.10 mmol), and 2-dimethylaminoethanol (0.5 mL) were irradiated in a quartz vessel of 10 mL capacity by a microwave oven at 140 ◦ C and 200 W for 3 min. The resulting dark green solid was filtered off, washed several times with diethyl ether, and dried in vacuo. UV-Vis (DMSO): λ, nm (log ε) 299 (4.32), 684 (4.25). IR νmax/cm −1: 3059 (C-H, aromatic), 2953–2860 (C-H, aliphatic), 1255 (C-O-C).1H NMR (500 MHz; CDCl3): δ 2.21 (24H, s, CH3), 3.17 (36H, s, CH3), 3.26 (8H, br, CH2-N), 3.41 (8H, br, CH2-N), 3.82 (8H, br, CH2-N), 5.23 (8H, br, CH-O), 7.46–8.04 (12H, m, Ar). Analysis of C68H104I8N16O4Zn (2290.30) (% calcd./found): C 35.66/ 35.70, H: 4.58/ 4.78, N: 9.78/ 9.95. 4. Conclusion The synthesis and the characterization of Pcs with 4 amino-based substituents have been reported and these new complexes were characterized by elemental analysis, FT-IR, 1H NMR spectroscopy, and electronic spec- troscopy. The synthesized Pcs are highly soluble in common organic solvents such as THF, chloroform, and dichloromethane. The quaternized products are soluble in water. For this reason, these compounds deserve further research for their properties as photosensors.