Comparatively singlet oxygen efficiency by sono-photochemical and photochemical studies of new lutetium (III) phthalocyanines

Synthesis, Photophysical and Biological Properties of New Phthalocyanines Bearing Peripherally 4‐(Trifluoromethoxy)phenoxy Groups

Non-symmetrical metallophthalocyanines (MPc), in which M is zinc(II), chloromanganese(III), or cobalt(II), containing a thiazole ring in their peripheries were synthesized by the statistical condensation of two different phthalonitriles, namely 4-(4-phenyl-2-thiazolyl)thiophthalonitrile (1) and 4-tert-butylphthalonitrile (2). The newly prepared compounds were characterized via elemental analysis techniques, including ultraviolet-visible spectrophotometry, Fourier transform infrared spectroscopy, proton nuclear magnetic resonance spectroscopy and mass spectrometry. The redox properties of the MPcs were tested via cyclic and square wave voltammetry methods. The redox results elucidated the effects of the metal centers and electrolytic systems on the electrochemical activities of the designed phthalocyanine complexes. The heavy metal ion recognition abilities of these complexes were also analyzed by employing an AT-cut quartz crystal resonator with a fundamental resonance frequency of 10 MHz. The results revealed that Cu2+ at a concentration of 0.40 mg L−1 in the aqueous solution caused a ∼31 kHz frequency shift of the quartz crystal coated with a thin film of MnPc (5). This considerable observed shift in the resonance frequency indicated the powerful sensing ability of compound 5 to detect Cu2+ ions, even in liquid phase. Furthermore, the heavy metal ion sensing results showed that this examined sensitivity of the QCM-based sensor strongly depends upon the atomic radius of the metal ions in aqueous solution.

Thiazole-substituted non-symmetrical metallophthalocyanines: synthesis, characterization, electrochemical and heavy metal ion sensing properties

Nonlinear optical properties of peripheral symmetrically and non-symmetrically 4-(trifluoromethoxy)phenoxy substituted zinc phthalocyanines

Measurement of improved singlet oxygen generations of indium chloride phthalocyanines by comparatively sono-photochemical and photochemical studies

This study presents a novel phthalonitrile derivative (2) bearing (trifluoromethoxy)phenoxy groups in 4,5 positions. Cyclotetramerization of (2) in N,N-dimethylaminoethanol (DMAE) gave a series of ...

Antimicrobial and antioxidant properties of novel octa-substituted phthalocyanines bearing (trifluoromethoxy) phenoxy groups on peripheral positions

This study presents the preparation of a novel tetra-substituted phthalonitrile (1), namely, 3,6-bis(hexyloxy)-4,5-bis(4-(trifluoromethoxy)phenoxy)phthalonitrile (1) and its metal-free (2)/metal {M = Zn (3), Cu (4), Co (5), Lu(CH3COO) (6), Lu (7)} phthalocyanines. A series of various spectroscopic methods (UV-vis, FT-IR, mass, and 1H NMR spectroscopy) were performed for the characterization of the newly synthesized compounds. The potential of compounds 2, 3, and 6 as photosensitizing materials for photodynamic and sonophotodynamic therapies was evaluated by photophysical, photochemical, and sonochemical methods. The highest singlet quantum yields were obtained for the zinc phthalocyanine derivative 3 by performing photochemical and sonochemical methods. In addition, several biological activities of the new compounds 1–7 were investigated. The newly synthesized phthalocyanines exhibited excellent DPPH scavenging activity and also DNA nuclease activity. The antimicrobial activity of the new compounds was evaluated by the disc diffusion assay. Effective microbial cell viability inhibition was observed with phthalocyanine macromolecules. The photodynamic antimicrobial therapy of the phthalocyanines showed 100% bacterial inhibition when compared to the control. They also exhibited significant biofilm inhibition activity against S. aureus and P. aeruginosa. These results indicate that new phthalocyanines are promising photodynamic antimicrobial therapies for the treatment of infectious diseases.

Nazli Farajzadeh

Papers

Comparatively singlet oxygen efficiency by sono-photochemical and photochemical studies of new lutetium (III) phthalocyanines

Antimicrobial and antioxidant properties of novel octa-substituted phthalocyanines bearing (trifluoromethoxy) phenoxy groups on peripheral positions

Synthesis, Photophysical and Biological Properties of New Phthalocyanines Bearing Peripherally 4‐(Trifluoromethoxy)phenoxy Groups

Nonlinear optical properties of peripheral symmetrically and non-symmetrically 4-(trifluoromethoxy)phenoxy substituted zinc phthalocyanines

Photophysicochemical, sonochemical, and biological properties of novel hexadeca-substituted phthalocyanines bearing fluorinated groups.