Synthesis and characterization of novel 2-{[2-(dimethylamino)ethyl](methyl)amino} ethoxy-substituted metallophthalocyanines
The synthesis of novel, symmetrical, tetrasubstituted metallophthalocyanines (cobalt, zinc, and copper) bearing four 2-{[2-(dimethylamino)ethyl](methyl)amino} ethoxy units was reported. The dinitrile derivative was converted into the water-soluble quaternized product by its reaction with methyl iodide. The quaternized zinc phthalocyanine was obtained from the reaction of the water-soluble dinitrile derivative with zinc acetate. The structures of the newly synthesized molecules were proposed according to elemental analysis, 1H NMR, FT-IR, and UV-Vis spectral data.
Synthesis and characterization of novel 2-{[2-(dimethylamino)ethyl](methyl)amino} ethoxy-substituted metallophthalocyanines
The synthesis of novel, symmetrical, tetrasubstituted metallophthalocyanines (cobalt, zinc, and copper) bearing four 2-{[2-(dimethylamino)ethyl](methyl)amino} ethoxy units was reported. The dinitrile derivative was converted into the water-soluble quaternized product by its reaction with methyl iodide. The quaternized zinc phthalocyanine was obtained from the reaction of the water-soluble dinitrile derivative with zinc acetate. The structures of the newly synthesized molecules were proposed according to elemental analysis, 1H NMR, FT-IR, and UV-Vis spectral data.
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- 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.