Synthesis of tetra-substituted phthalocyanines bearing 2-(ethyl(m-tolyl)amino)ethanol: Computational and photophysicochemical studies

Add time:07/17/2019    Source:sciencedirect.com

This work presents the synthesis of 4-(2-(ethyl(m-tolyl) amino) ethoxy) phthalonitrile (1) as ligand and its peripherally tetrasubstituted metal-free (2) and metallophthalocyanines (3–5) derivatives. Synthesized compounds were characterized by standart spectroscopy methods. The molecular structure of the ligand (1) was confirmed by single-crystal X-ray diffraction experiment. The crystallographic information file (cif) was uploaded to the data center with CCDC number 1,853,485. The optimized structure of the ligand (1) and the phthalocyanines (2–5) were obtained by using different metods such as B3lyp, HF and m062x method 3–21 g, 6–31 g, sdd basis set. In b3lyp/6–31++g(d,p) basis set, 1H and 13C NMR chemical shifts, IR spectrum and UV–vis spectrum were measured in gas, chloroform and dimethylsulfoxide phase by means of the obtained optimized structure. Besides, the photophysical and photochemical properties of newly synthesized phthalocyanines (2–5) were investigated in DMSO, comparatively. Singlet oxygen quantum yields of the phthalocyanines (2–5) are ranging from 0.28 to 0.70.

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