Synthesis, DFT analysis, and electronic properties of new phthalocyanines bearing ETAEO substituents on peripheral position


Cabir B., YILDIKO Ü., Ağırtaş M. S.

JOURNAL OF COORDINATION CHEMISTRY, vol.72, no.17, pp.2997-3011, 2019 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 72 Issue: 17
  • Publication Date: 2019
  • Doi Number: 10.1080/00958972.2019.1680832
  • Journal Name: JOURNAL OF COORDINATION CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2997-3011
  • Keywords: Phthalocyanine, synthesis, fluorescence, characterization, metal, NBO, METAL-FREE, PHOTOCHEMICAL PROPERTIES, NICKEL PHTHALOCYANINE, COPPER PHTHALOCYANINE, THIN-FILMS, DEGRADATION, ANTIOXIDANT, ZINC(II), HOMO, LUMO
  • Van Yüzüncü Yıl University Affiliated: Yes

Abstract

This study reports the synthesis of new zinc and magnesium phthalocyanine compounds with ((ethylenediamine-N,N ',N '-triacetic acid-N-2-ethyl)oxy) (ETAEO) substituted groups. A novel compound, (4-ETAEO) phthalonitrile, for the starting material of these phthalocyanines was synthesized. The exact characterization of the compounds was carried out with H-1 NMR, IR, UV-Vis, and mass spectra. Fluorescence intensity of these metallophthalocyanines (MPcs) was investigated at 1 x 10(-5) M concentration in tetrahydrofuran (THF). Electronic absorption measurements of the phthalocyanine compounds in the tetrahydrofuran were performed. Photodegradation was performed in dimethylformamide (DMF). Optimized structure, boundary molecular orbitals (HOMO and LUMO), natural bond orbital (NBO) analysis and global reactivity descriptors were analyzed by DFT calculations.