Novel phthalocyanines bearing 4-(2-isopropylphenoxy) groups: Synthesis, characterization, electrochemical and in-situ spectroelectrochemical properties

DEMİRBAŞ Ü., Akyüz D.

JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol.1017, 2024 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1017
  • Publication Date: 2024
  • Doi Number: 10.1016/j.jorganchem.2024.123272
  • Journal Name: JOURNAL OF ORGANOMETALLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, Index Chemicus (IC)
  • Keywords: Cobalt(II) phthalocyanine, Electrochemistry, Isopropylphenoxy, Spectroelectrochemistry, Zinc(II) phthalocyanine
  • Karadeniz Technical University Affiliated: Yes

Abstract

In this study, 4-(2-isopropylphenoxy)phthalonitrile (3) was prepared via a substitution reaction between 2-isopropylphenol (1) and 4-nitrophthalonitrile (2). Then, peripherally tetra 2-isopropylphenoxy substituted zinc (II) (4) and cobalt(II) (5) phthalocyanines were obtained via a cyclotetramerization reaction between phthalonitrile (3) and related metal salt. The structural characterization of synthesized compounds were completed via FT-IR, 1HNMR , UV-Vis and MALDI-TOF mass data. Electrochemical and spectroelectrochemical measurements were performed to determine the potential of novel phthalocyanines to be used in electrochemical applications. While the cobalt(II) phthalocyanine (5) displayed one metal-based reduction, two ring-based reductions and one metal and ring-based oxidation; zinc(II) phthalocyanine (4) showed three ring-based reductions and one ringbased oxidation reaction. In addition, it was determined that electron-releasing isopropyl phenoxy group affected half-wave peak potentials of complexes and the Q band positions. Diffusion-controlled, reversible and multi-electron transfer abilities of the zinc(II) (4) and cobalt(II) (5) phthalocyanines showed that they have redox richness for can be used in optical technological applications.