Octa- and tetra-substituted phthalocyanines with methoxyeugenol group: synthesis, characterization and in vitro antimicrobial activity

Kamiloglu A. A., Direkel S., Yalazan H., KANTEKİN H., ACAR İ.

JOURNAL OF COORDINATION CHEMISTRY, vol.73, no.7, pp.1177-1190, 2020 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 73 Issue: 7
  • Publication Date: 2020
  • Doi Number: 10.1080/00958972.2020.1761962
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chimica, Metadex
  • Page Numbers: pp.1177-1190
  • Keywords: Octa-phthalocyanine, eugenol, characterization, metallophthalocyanine, antimicrobial activity, OXYGEN REDUCTION, EUGENOL, FASTNESS
  • Karadeniz Technical University Affiliated: Yes


In this study, the novel phthalonitrile derivatives 1 and 2 were synthesized. Tetra-substituted metal-free 1a (H2Pc) and metallophthalocyanines (ZnPc 1b, CoPc 1c and CuPc 1d) bearing four peripheral 4-allyl-2,6-dimethoxyphenol (methoxy-eugenol) groups and octa-substituted metal-free 2a and metallophthalocyanines (ZnPc 2b, CoPc 2c and CuPc 2d) bearing eight peripheral methoxy-eugenol group were synthesized. All new synthesized compounds are characterized by IR, C-13{H-1} NMR (for 1 and 2), UV-Vis (for 1a-2d) and mass spectroscopy. Antimicrobial activities of the synthesized phthalonitrile derivatives (1 and 2) and phthalocyanine compounds 1a-2d were determined by microdilution broth method against nine different bacteria and one yeast species. In this study, CoPc (2c) compound, which has eight peripheral 4-allyl-2,6-dimethoxyphenol, had the highest antibacterial activity (minimum inhibitory concentration [MIC] = 312 mu g/mL). In addition, 1b, 1d, 2b and 2d were found to be effective on at least three different bacterial species at different concentrations (MIC = 1250-5000 mu g/mL). Shigella flexneri were the most affected bacteria, but none of the compounds were effective against fungal isolate.