Novel symmetrical and unsymmetrical fluorine-containing metallophthalocyanines: synthesis, characterization and investigation of their biological properties

Hande Pekbelgin Karaoğlu, Özgül Sağlam, Sadin Özdemir, Serpil Gonca, Makbule Burkut Koçak*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

In this study, a new fluorinated phthalonitrile compound namely 5-bis[4-(trifluoromethoxy)-thiophenyl] phthalonitrile was synthesized. In addition, peripherally substituted symmetric metallated phthalocyanine derivatives [M = Co (2) and M = Zn (3)] and unsymmetrically substituted zinc phthalocyanine (ZnPc) complex (4) were synthesized by cyclotetramerization of this phthalonitrile compound. Characterization of all new compounds was carried out using FT-IR, NMR, UV-Vis, and mass spectroscopy. Additionally, antioxidant activity, DNA cleavage activity, antimicrobial activity, biofilm inhibition activity, and bacterial viability inhibition test of the compounds (1-4) were investigated. The antioxidant activities of the new phthalocyanine complexes were studied by performing two different methods. The results indicated that the highest DPPH (1,1-diphenyl-2-picrylhydrazyl) free radical scavenging activity was determined to be 67.85% for2and also3showed the highest activity with 31.65% for chelating activity at 200 mg L−1concentration. Phthalocyanine compounds demonstrated effective DNA cleavage and antimicrobial activities. The highest percentage of cell vitality inhibition was found for compound4, 56.92%. Also, test compounds exhibited good biofilm inhibition activity.

Original languageEnglish
Pages (from-to)9700-9708
Number of pages9
JournalDalton Transactions
Volume50
Issue number28
DOIs
Publication statusPublished - 28 Jul 2021

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Publisher Copyright:
© The Royal Society of Chemistry 2021.

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