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

Gunsel A., Bilgicli A. T., TÜZÜN B., Piskin H., Atmaca G., ERDOĞMUŞ A., ...More

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, vol.373, pp.77-86, 2019 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 373
  • Publication Date: 2019
  • Doi Number: 10.1016/j.jphotochem.2018.12.038
  • Journal Name: JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.77-86
  • Keywords: Phthalocyanine, Synthesis, Computational studies, Crystal structure, Photochemistry, MOLECULAR-DYNAMICS SIMULATION, CORROSION-INHIBITORS DFT, METAL-FREE, ZINC(II) PHTHALOCYANINES, PHOTOCHEMICAL PROPERTIES, ELECTROCHEMICAL PROPERTIES, THEORETICAL EVALUATION, BASE-PAIR, DERIVATIVES, AGGREGATION
  • Yıldız Technical University Affiliated: Yes

Abstract

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, H-1 and C-13 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.