Octa-substituted Zinc(II), Cu(II), and Co(II) phthalocyanines with 1-(4-hydroxyphenyl)propane- 1-one: Synthesis, sensitive protonation behaviors, Ag(I) induced H-type aggregation properties, antibacterial– antioxidant activity, and molecular docking studies
Tarih
18 June 20Yazar
Bilgiçli, Ahmet T.Kandemir, Tugberk
Arıduru, Rana
Günsel, Armagan
Abak, Çagla
Yarasir, M. Nilüfer
Arabaci, Gulnur
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Tüm öğe kaydını gösterKünye
1Department of Chemistry, Sakarya University, Sakarya, Turkey 2Department of Chemistry, Cumhuriyet University, Sivas, TurkeyÖzet
This study shows the synthesis and characterization of 4,5-bis(4-propionylphenoxy)
phthalonitrile (2) and its octa-substituted phthalocyanine
derivatives [ZnPc(3), CuPc(4), and CoPc(5)]. A combination of standard
spectroscopic techniques has characterized the newly synthesized
phthalonitrile derivative and phthalocyanines. The aggregation behaviors of
new octa-substituted phthalocyanines have been evaluated by ultraviolet–
visible (UV-vis) spectroscopy. The metal ion-sensitive behaviors of new
octa-substituted phthalocyanines in the presence of soft metal ions have been
performed by UV-vis and fluorescence spectrophotometer. The quenching
efficiency (Ksv) of Ag+ ions against ZnPc(3) was found using the Stern–Volmer
equation. The binding constant (Ka) and binding stoichiometry (n) of ZnPc(3)
with Ag+ ions were calculated using the modified Benesi–Hildebrand
equation. Sensitive protonation behaviors of octa-substituted phthalocyanines
have been investigated by titration experiments as well as computational
calculations. The ZnPc(3) and CuPc(4) were exhibited H-type aggregation
behaviors toward Ag+ ions. However, the protonation of octa-substituted zinc
and copper phthalocyanine during the titration with HCl caused J-type selfaggregation
properties. In vitro antioxidant properties of the new compounds
were investigated by the radical scavenging ability of 1,1-diphenyl-
2-picrylhydrazyl (DPPH), chelating ability to ferrous ions, and reducing power
methods. Additionally, in vitro antibacterial activities of the octa-substituted
phthalocyanines were determined. Finally, optimized structures of novel
compounds [(2), ZnPc(3), CuPc(4), and CoPc(5)] were obtained on the HF
(Hartree–Fock), B3LYP (Becke, 3-parameter, Lee-Yang-Parr), M06–2X
methods with 3–21 g, 6–31 g and SDD basis set. Then, biological activities of novel phthalonitrile and its phthalocyanine derivatives toward breast, liver,
and lung cancer proteins were compared with molecular docking studies.