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., ...Daha Fazla

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, cilt.373, ss.77-86, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 373
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1016/j.jphotochem.2018.12.038
  • Dergi Adı: JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.77-86
  • Anahtar Kelimeler: 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 Teknik Üniversitesi Adresli: Evet

Özet

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.