Synthesis and electrochemistry of new octa-substituted metal-free and metallophthalocyanines


ACAR İ., SAKA E. T. , Topcu S., BIYIKLIOĞLU Z., KANTEKİN H., AKTAS A.

JOURNAL OF COORDINATION CHEMISTRY, vol.68, no.10, pp.1847-1858, 2015 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Volume: 68 Issue: 10
  • Publication Date: 2015
  • Doi Number: 10.1080/00958972.2015.1022537
  • Journal Name: JOURNAL OF COORDINATION CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.1847-1858

Abstract

The synthesis and characterization of metal-free (H-2-Pc) and metal-containing (Zn, Co, and Cu) derivatives of a symmetrically octa-substituted phthalocyanine derived from 4,5-bis[2-(phenylthio)ethoxy]phthalonitrile were carried out by microwave irradiation. The electrochemical properties of the metal-free phthalocyanine 4 and metallophthalocyanine complexes 5 and 6 were investigated by cyclic voltammetry and differential pulse voltammetry. We have previously investigated the electrochemical properties of the tetra substituted 2-(phenylthio)ethoxy phthalocyanines. The reduction potential of the octa-substituted metal-free phthalocyanine shifted to more negative potential as a result of the electron donating of the 2-(phenylthio)ethoxy groups on the periphery compared to those of tetra substituted. The H2Pc and ZnPc demonstrated ligand-based electron transfer processes, while CoPc complex has a metal-based reduction process. Similar aggregation behavior was observed for octa-substituted phthalocyanines. The compounds were characterized using IR, H-1 NMR, C-13 NMR, elemental analysis, and MS spectral data.