Synthesis and electrochemistry of non-aggregated axially disubstituted silicon phthalocyanines bearing benzoxazin substituents

Bıyıklıoğlu, Zekeriya; Baş, Hüseyin

doi:10.1016/j.ica.2015.01.023

Cited by 14 publications

(4 citation statements)

References 32 publications

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“…Aggregation of phthalocyanines is dependent on the solvent, concentration, substituents, and complex metal ions. [38] In this study, aggregation behaviors of DFP-Si, DFP-Cu, and DFP-Mn in solution were examined by UV-Vis spectrophotometer in different solvents and concentrations. Figures 4a, 5a 4b, 5b, and 6b show the UV-Vis spectra of the DFP-Si, DFP-Cu, and DFP-Mn in different concentrations in CHCl 3 (concentration ranges 2-12 Â 10 À6 M).…”

Section: Aggregation Propertiesmentioning

confidence: 99%

Synthesis, characterization, and α‐glucosidase, cholinesterases, and tyrosinase inhibitory effects of axial substituted silicon and peripheral tetra‐substituted copper (II), manganese (III) phthalocyanines

Öztürmen

Barut

Bıyıklıoğlu

2022

Applied Organom Chemis

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In this paper, we have synthesized axially di‐(3,3‐diphenylpropoxy) substituted silicon (DFP‐Si) and peripherally tetra‐(3,3‐diphenylpropoxy) substituted copper (II), manganese (III) phthalocyanines (DFP‐Cu, DFP‐Mn). Then, the α‐glucosidase, acetylcholinesterase, butyrylcholinesterase, and tyrosinase inhibitory effects of DFP‐Si, DFP‐Cu, and DFP‐Mn were examined using spectrophotometric methods. DFP‐Mn had the highest inhibitor effect on cholinesterases, tyrosinase, and α‐glucosidase in a concentration‐dependent manner. DFP‐Mn inhibited α‐glucosidase with IC50 value of 17.80 μM. Also, DFP‐Mn also showed higher α‐glucosidase inhibitory actions that acarbose used as a positive control. The inhibition percentages in the presence of DFP‐Mn were 30.64 ± 2.24%, 51.96 ± 1.56%, and 72.96 ± 4.95%, respectively at 20, 40, and 100 μM on AChE. In the presence of DFP‐Mn at 100 μM, the inhibition percentages were calculated as 52.18 ± 2.22% against tyrosinase. These results showed that the compound has potential to treat Diabetes mellitus but further studies are needed to confirm the antidiabetic effect of the compound.

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Section: Aggregation Propertiesmentioning

confidence: 99%

Synthesis, characterization, and α‐glucosidase, cholinesterases, and tyrosinase inhibitory effects of axial substituted silicon and peripheral tetra‐substituted copper (II), manganese (III) phthalocyanines

Öztürmen

Barut

Bıyıklıoğlu

2022

Applied Organom Chemis

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“…To overcome this problem, the introduction of substituents at the axial positions of phthalocyanines is preferred because the axial positions can strongly influence some properties of phthalocyanines such as its solubility and aggregation behavior. 15,16 For this reason, non-aggregating and water soluble axially disubstituted silicon phthalocyanines (SiPcs) can be used in biological applications. Previous researches have also demonstrated that toxicity of SiPcs are very low against cancer cells.…”

Section: Introductionmentioning

confidence: 99%

The synthesis of axially disubstituted silicon phthalocyanines, their quaternized derivatives and first inhibitory effect on human cytosolic carbonic anhydrase isozymes hCA I and II

2018

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“…In this study, first the zinc(II) phthalocyanines containing octa-substituted with hexyl-linked carbazole in the nonperipheral positions and carbazole-substituted disulfur compounds were synthesized and characterized. It is well-known that some properties of phthalocyanines such as NIR shifting of the Q-band, decrease in aggregation, high triplet quantum yield, physicochemical properties, and solubility depend on the position or types of substituents (α, β; S, O) and metals. ,− Compared to the same substituents substituted at different positions in zinc or metal-free phthalocyanines according to the electropolymerization, electro-optic and biosensor properties should be significant. In this work, optical, electrical, and sensing properties of superstructured zinc(II) phthalocyanine nonperipherally alkyl-linked polycarbazole have been compared with peripherally alkyl-linked polycarbazole-based zinc(II) phthalocyanine.…”

Section: Introductionmentioning

confidence: 99%

Comparative Investigation of Peripheral and Nonperipheral Zinc Phthalocyanine-Based Polycarbazoles in Terms of Optical, Electrical, and Sensing Properties

Soganci

Bayğu

Kabay

et al. 2018

ACS Appl. Mater. Interfaces

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In this study, nonperipherally alkyl-linked carbazole conjugated novel zinc(II) phthalocyanine was synthesized by cyclotetramerization reaction of 6-(9 H-carbazol-9-yl)hexane-1-thiol and 3,6-bis(tosyloxy) phthalonitrile in a one-step reaction. Optical, electrical, and sensing properties of this super structured polycarbazole obtained by electropolymerization are compared with peripherally alkyl-linked polycarbazole-based zinc(II) phthalocyanine. It has been found that the attachment of alkyl-linked carbazoles to the phthalocyanine molecule in either peripheral or nonperipheral positions has a great effect on the optical and electrical properties and sensing ability of the resulting polycarbazole derivatives. P(n-ZnPc) has the highest electrochromic contrast (70.5%) among the derivatives of zinc(II) phthalocyanines in the literature. In addition to these, the sensor platform has been successfully established, and analytical optimizations have been carried out. When the sensors prepared with zinc(II) phthalocyanine are examined, it was specified that the n-ZnPc- co-TP/GOx was ranked first in the literature with high sensor response and stability. As a result, by changing of the peripheral and nonperipheral position of phthalocyanines, their physical properties can be tuned to meet the requirements of desired technological application.

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Synthesis and electrochemistry of non-aggregated axially disubstituted silicon phthalocyanines bearing benzoxazin substituents

Cited by 14 publications

References 32 publications

Synthesis, characterization, and α‐glucosidase, cholinesterases, and tyrosinase inhibitory effects of axial substituted silicon and peripheral tetra‐substituted copper (II), manganese (III) phthalocyanines

Synthesis, characterization, and α‐glucosidase, cholinesterases, and tyrosinase inhibitory effects of axial substituted silicon and peripheral tetra‐substituted copper (II), manganese (III) phthalocyanines

The synthesis of axially disubstituted silicon phthalocyanines, their quaternized derivatives and first inhibitory effect on human cytosolic carbonic anhydrase isozymes hCA I and II

Comparative Investigation of Peripheral and Nonperipheral Zinc Phthalocyanine-Based Polycarbazoles in Terms of Optical, Electrical, and Sensing Properties

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