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

Photochem & Photobiology

Özdemir

Gonca

et al. 2021

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As thiazoles and fluorinated groups are well known as active species of hybrid pharmaceutical agents, this study aimed to evaluate the synergic effect of these groups on the biological features of phthalocyanines for the first time in the hope of discovering efficient pharmaceutical agents. Therefore, a new phthalonitrile derivative namely 4‐(2‐(4‐methylthiazol‐5‐yl)ethoxy)‐5‐(4‐(trifluoromethoxy)phenoxy)phthalonitrile (1) and its metal‐free (2)/metal phthalocyanines (3‐5) were prepared and characterized using various spectroscopic techniques. Solubility of new phthalocyanines (2‐5) was examined in a series of polar and nonpolar solvents. Additionally, sono/photochemical methods were applied to examine the photophysical and sono/photochemical properties of new zinc phthalocyanine to measure its potential as a probable material for sono/photodynamic therapies. The antioxidant activities of compounds (1‐5) were evaluated using the DPPH scavenging activity method and the highest radical scavenging activity was obtained 92.13% (200 mg L−1) for manganese phthalocyanine. All the phthalocyanines demonstrated high DNA nuclease activity, as well. The antimicrobial activities of compounds (1‐5) were investigated using disk diffusion and microdilution methods. The phthalocyanines exhibited effective microbial cell inhibition activity against Escherichia coli (E. coli). Antimicrobial photodynamic therapy activity was investigated against E. coli by LED irradiation. Compounds (2‐5) acted as photosynthesizers. Also, they displayed significant biofilm inhibition activity against Staphylococcus aureus (S. aureus) and Pseudomonas aeruginosa (P. aeruginosa).

Section: Introductionmentioning

confidence: 99%

“…Our group also has been reported the synthesis, and characterization of different fluorine‐containing phthalocyanines. The biological, electrochemical and optical properties of these fluorinated phthalocyanines were examined, as well (35–46).…”

Section: Introductionmentioning

confidence: 99%

Photophysicochemical and Biological Properties of New Phthalocyanines Bearing 4‐(trifluoromethoxy)phenoxy and 2‐(4‐methylthiazol‐5‐yl)ethoxy Groups on Peripheral Positions

Photochem & Photobiology

Özdemir

Gonca

et al. 2021

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“…Since compound 1a obeys the Lambert–Beer law, aggregation does not rely on concentration at the studied range of concentration (Fig. 5) (29–34,41,42).…”

Section: Resultsmentioning

confidence: 99%

“…Spectral properties of Pcs as a function of the electronic states change by enhancement of p-stacking which derange of the electronic states. Furthermore, the study of the electronic absorption spectra of Pcs is a useful approach for measurement and management of their aggregation (1)(2)(3)(4)(29)(30)(31)(32)(33)(34)41,42).…”

Section: Aggregation Studiesmentioning

confidence: 99%

Effect of Position and Connected Atom on Photophysical and Photochemical Properties of Some Fluorinated Metallophthalocyanines

Sağlam

Photochem & Photobiology

Atmaca

et al. 2020

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This study presents the preparation of a new phthalonitrile derivative namely 3‐(4‐(trifluoromethoxy)thiophenoxy)phthalonitrile (1) and a series of its metallated phthalocyanines (M = Zn (II) (1a) and In(III) (1b)). In addition, the peripheral analog of the indium phthalocyanine chloride (2b) was newly synthesized. Characterization of the resulting compounds was carried out by utilizing various spectroscopic methods such as FT‐IR, 1H NMR and UV‐Vis spectroscopy. The influence of concentration on aggregation properties of compound 1a was investigated at different concentrations of DMSO. The effect of solvent type on aggregation properties of compound 1a was studied, as well. According to the referred procedures, the macrocyclic molecules (2a, 3a‐b and 4a‐b) were prepared. The effect of some parameters including metal ion, the position of the substituent and the connected atom (oxo or thio) on photochemical and photophysical features of compounds (1a‐b, 2a‐b, 3a‐b, and 4a‐b) was studied for evaluation of their potential as a photosensitizer in PDT, comparatively. The highest singlet oxygen quantum yields (ΦΔ = 0.71 for 1a and 0.80 for 2b) were obtained for complexes 1a and 1b in DMSO. The photophysical and photochemical features of the studied macromolecules are therefore suitable for photodynamic therapy applications.

“…Recently, our group has concentrated on investigating the advantages of the synthesis and characterization of the fluorinated Pcs as suitable materials for chemical, biological, physical, and medical applications. [ 14,24–30 ] This study reports the preparation and characterization of new peripherally/nonperipherally substituted Pcs bearing 4‐(trifluoromethoxy)thiophenyl or 4‐(trifluoromethoxy)phenoxy substituents. In addition, the effect of the position and connected atom on the biological properties of the newly synthesized Pcs was examined.…”

Section: Introductionmentioning

confidence: 99%

Investigation of tyrosinase enzyme (from mushroom) inhibitory activities and antioxidant properties of new fluorine‐containing phthalocyanines

Sağlam

Akın

et al. 2020

Archiv der Pharmazie

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A series of new peripherally or nonperipherally substituted phthalocyanines bearing 4‐(trifluoromethoxy)thiophenyl groups was synthesized. In addition, a new metal‐free phthalocyanine bearing 4‐(trifluoromethoxy)phenoxy on the nonperipheral position was prepared. The resulting phthalocyanines were characterized using some spectroscopic techniques such as 1H nuclear magnetic resonance, Fourier‐transform infrared spectroscopy, and UV–Vis spectroscopy, together with elemental analysis. When the tyrosinase enzyme inhibition activities of the synthesized phthalocyanines were examined, molecules 2b and 3b showed an inhibitory activity against the enzyme with IC50 values of 176.2 ± 0.65 and 284.4 ± 1.03, respectively. The inhibition types of the molecules and standard inhibitor kojic acid were found as competitive for 2b, mixed for 1b and kojic acid, and uncompetitive for 3b. Antioxidant activities were also assessed by using 1,1‐diphenyl‐2‐picrylhydrazyl (DPPH) and reducing power assays, and the molecules showed moderate antioxidant activities.