1,4-Dithiaheterocycle-fused porphyrazines: Synthesis, characterization, voltammetric and spectroelectrochemical properties

Tuncer S., KOCA A., Guel A., Avciata U.

DYES AND PIGMENTS, vol.81, no.2, pp.144-151, 2009 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 81 Issue: 2
  • Publication Date: 2009
  • Doi Number: 10.1016/j.dyepig.2008.09.022
  • Journal Name: DYES AND PIGMENTS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.144-151
  • Yıldız Technical University Affiliated: Yes


Porphyrazines (M = H, Mg, Zn and Co) with a 2,3-dicyano-5-phenyl-5,6-dihydro-1,4-dithiin group fused to each pyrrole unit were synthesized and characterized starting with the corresponding unsaturated dicarbonitrile derivative. The voltammetric and spectroelectrochemical characterizations of the metallo-porphyrazines (M=2H(+), Mg2+, Zn2+ and Co2+) substituted with 2,3-dicyano-5-phenyl-5,6-dihydro-1,4-dithiin groups on peripheral positions are described. Cyclic voltammetry and differential pulse voltammetry studies showed that while metal-free, magnesium, and zinc porphyrazines represented well-defined one-electron ligand-based reductions and ligand-based one-electron oxidation couples, cobalt porphyrazine gave both metal-based and ligand-based reduction and oxidation couples. Assignments of the redox couples were confirmed by spectroelectrochemical measurements. (C) 2008 Elsevier Ltd. All rights reserved.