Synthesis, electrochemical, in-situ spectroelectrochemical and in-situ electrocolorimetric characterization of new phthalocyanines containing macrocyclic moieties

• New phthalocyanine compounds containing optically active 1,1′-binaphthyl crown ethers units were synthesized.
• These new complexes were explained by using spectroscopic data and elemental analysis.
• Electrochemical properties of Co(II) and Zn (II) phthalocyanines were investigated by using cyclic voltammetry and differential pulse voltammetry techniques.

In this work, we synthesized new phthalocyanine compounds containing optically active 1,1′-binaphthyl crown ethers units. The metal-free phthalocyanine (3) was synthesized by the cyclotetramerization of dinitrile derivative (2) in dry n-pentanol by a classical method. However, metal phthalocyanines complexes (4, 5, 6), were synthesized by the reaction of dinitrile derivative (2) in DMAE. The structure of the new compounds were characterized by using spectroscopic data and elemental analysis. Electrochemical properties of Co (II) and Zn (II) phthalocyanines were investigated by using cyclic voltammetry and differential pulse voltammetry techniques. They exhibited two reversible Pc ring-based one-electron reduction couples. The Co (II) and Zn (II) phthalocyanines gave very similar voltammetric responses with slight potential shift due to different metal center.

In this work, new phthalocyanine compounds containing mixed-donor substituted macrocyclic groups were synthesized. The metal-free phthalocyanine (3) by cyclotetramerization of dinitrile derivative (2) was accomplished in dry n-pentanol in a Schlenk tube at reflux temperature under N2 (g) atmosphere. The complexes of metal phthalocyanines, such as, Co(II) (4), Cu(II) (5), Zn(II) (6) phthalocyanines were prepared by the reaction of (2) to get dinitrile derivative complexes by order of the, corresponding anhydrous metal salts. These new complexes were identified by using spectroscopic data and elemental analysis. Electrochemical properties of Co(II) and Zn(II) phthalocyanines were investigated by using cyclic voltammetry and differential pulse voltammetry techniques. They exhibit two reversible Pc ring-based one-electron reduction couples. The Co(II) and Zn(II) phthalocyanines give very similar voltammetric responses with slight potential shift due to different metal center.Figure optionsDownload as PowerPoint slide