The new zinc phthalocyanine having high singlet oxygen quantum yield substituted with new benzenesulfonamide derivative groups containing schiff base

Pişkin, Mehmet; Canpolat, Erdal; Öztürk, Ömer Faruk

doi:10.1016/j.molstruc.2019.127181

Cited by 24 publications

(30 citation statements)

References 24 publications

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“…The 1 H-and 13 C-NMR spectral results of the newly compounds 1, 2 and ZnPc 3 are in concordance with those of their counterparts in the literature [24,25]. The ZnPc 3 was also characterized by MALDI-TOF mass spectrometry using 2,5-dihydroxybenzoicacid as a MALDI matrix (Fig.…”

Section: Resultssupporting

confidence: 85%

“…S2 in ESI). The absence of sharp bond stretching vibration with weak or moderate intensity in the FTIR spectrum of the ZnPc 3 in the range 2210 cm -1 to 2280 cm -1 was attributed to the absence of the nitrile group and indicated its conversion to the ZnPc 3 [24][25][26][27] (Fig. S3 in ESI).…”

Section: Resultsmentioning

confidence: 99%

“…The aim of this study is to synthesize a new photosensitizer for PDT with su cient and suitable uorescence properties, photostability and high singlet oxygen generating ability, which combines three different bioactive groups Schiff base, benzenesulfonamide and phthalocyanine in a single structure.The effects of the presence of a new benzenesulfonamide derivative containing electron donor group as methoxy and Schiff base and strongly electron acceptor groups such as Schiff base, bromine, and pyridine on the Pc ring on spectroscopic, photophysicochemical properties were researched in dimethyl sulfoxide (DMSO). In addition, these properties of the new zinc(II) Pc 3 were compared with the properties of different benzenesulfonamide derivative substituted zinc(II) phthalocyanines and unsubstituted zinc(II) phthalocyanine presented in previous studies [24,25].…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis, Characterization and Photophysicochemical Properties of Zinc(Ii) Phthalocyanine With New Benzenesulfonamide Derivative Substituents

Öncül

Öztürk

Pişkin

2021

Preprint

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Novel (E)-4-((5-bromo-2-hydroxy-3-methoxybenzylidene)amino)-N-(pyridin-2-yl)benzenesulfonamide 1, (E)-4-((5-bromo-2-(3,4-dicyanophenoxy)-3-methoxybenzylidene)amino)-N-(pyridin-2-yl)benzene sulfonamide 2 and 2(3),9(10),16(17),23(24)-tetra-[(E)-4-((5-bromo-3-methoxy-2-(λ1-oxidanyl)benzyl idene)amino)-N-(pyridine-2-yl)benzenesulfonamide]phthalocyaninato zinc(II) phthalocyanine 3 were synthesized. Their (1-3) structures were illuminated with spectroscopic methods such as FT-IR, 1H NMR,13C NMR, UV–vis, MALDI-TOF mass spectra and also elemental analysis. The spectroscopic, photophysical and photochemical properties of the zinc(II) phthalocyanine 3 were investigated in dimethyl sulfoxide and its effects on the above mentioned properties were reported as a result of containing new type benzenesulfonamide derivatives as substituents. In addition, its above-mentioned properties were reported by comparing different species with those of their substituted and/or unsubstituted counterparts. The zinc(II) phthalocyanine 3 has photosensitizing abilities suitable and sufficient especially for photocatalytic applications.

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Section: Resultssupporting

confidence: 85%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Characterization and Photophysicochemical Properties of Zinc(Ii) Phthalocyanine With New Benzenesulfonamide Derivative Substituents

Öncül

Öztürk

Pişkin

2021

Preprint

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“…The ΦF value of the MgPc 2 was lower than unsubstituted magnesium (II) phthalocyanine in DMF [27], which implies that the presence of the 2,6-dimethoxyphenoxy units reduced the fluorescence quenching of the Pc molecule. The ΦF value of the MgPc 2 is similar and typical of the other studied magnesium (II) Pc in DMF [37][38][39][40][41][42][43][44][45][46][47]. Fluorescence lifetime (τF) refers to the average time a molecule stays in its excited state before fluorescing, and its value is directly related to that of ΦF, i.e.…”

Section: Fluorescence Quantum Yield and Lifetimesupporting

confidence: 56%

“…In DMF, the τF value of the substituted MgPc 2 is 4.65 ns and longer compared to unsubstituted magnesium (II) phthalocyanine [27], suggesting less quenching by substitution. The τF value of the MgPc 2 is typical for the metallo-phthalocyanines [37][38][39][40][41][42][43][44][45][46][47]. The natural radiative lifetime (τ0) and the rate constants for fluorescence (kF) value of the MgPc 2 are 5.81× 10 −7 s -1 and 17.22 ns, respectively.…”

Section: Fluorescence Quantum Yield and Lifetimementioning

confidence: 99%

Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine

Pişkin

Öztürk

Odabaş

2021

MANAS Journal of Engineering

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2(3),9(10),16(17),23(24)-tetrakis-2,6-dimethoxyphenoxy substituted magnesium (II) phthalocyanine, which has very good solubility in polar and non-polar solvents and does not aggregate, was synthesized. Its structure was characterized by spectroscopic methods such as elemental analysis, UV-vis, FT-IR, MALDI-TOF mass and 1 H NMR. It has very good solubility in polar aprotic solvents such as dimethyl sulfoxide, N, N-Dimethylformamide, tetrahydrofuran, dichloromethane, and non-polar solvents such as toluene, chloroform. Its aggregation properties have been studied both in the solvents mentioned above and in N, N-Dimethylformamide at different concentrations. Its photophysical properties were determined in N, N-dimethyl formamide. The effects of the nature and presence of 2,6-dimethoxyphenoxy group, which is an antioxidant derivative, on the phthalocyanine skeleton on the spectroscopic and photophysical properties were investigated by comparing it with unsubstituted magnesium (II) phthalocyanine. It can be a good nominee for various technological applications in that it does not aggregate and has good solubility in polar and non-polar solvents, as well as better and favorable fluorescence properties than its analog in the previous study.

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Tumor‐pH‐value responsive non‐peripheral substituted phthalocyanines: Synthesis, investigation of photophysical and photochemical properties

Genc Bilgicli,

Bilgiçli,

Alagöz

et al. 2023

Applied Organom Chemis

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Cancer is one of the diseases with the highest mortality rate worldwide. Although PDT has recently produced encouraging outcomes, there are still many areas that need to be improved. The first of these is the negative consequences faced by patients treated with the PDT method when exposed to sunlight. For this reason, a new PDT method has been developed in recent years, and it is aimed at using photosensitizer molecules that can be active in acidic conditions. Since the pH values of tumor tissues are more acidic than normal tissues, preparing molecules that act effectively in acidic conditions will allow for more effective results in treating cancer with PDT. In this context, within the scope of this study, 3‐(4‐propionylphenoxy)phthalonitrile (1) and its non‐peripheral tetra‐substituted phthalocyanine derivatives [(2), (3), and (4)] were prepared. With these phthalocyanine derivatives, the novel compounds (5), (6), and (7) were synthesized for the first time. The aggregation tendencies of newly synthesized phthalocyanines (5–7) were investigated in solvent media. The effects of pH changes upon UV–Vis and fluorescence spectra were performed. The electronic and emission spectra of synthesized phthalocyanine derivatives are highly sensitive to pH changes. Formation constant (LogK) values of mono‐ and di‐protonated phthalocyanine forms were calculated by the Henderson–Hasselback equation. The mono‐ and di‐protonated species' equilibrium constants (logK1 and logK2) were calculated as ~5.0. This value may be promising for pH‐sensitizing photosensitizers. Also, the photophysical and photochemical properties of synthesized metallophthalocyanine derivatives (2) and (5) were studied at different pH values. The singlet oxygen quantum yield of (2) and (5) was calculated to be 0.78 and 0.81 in DMSO, respectively. When pH = 6.4, that is, tumor‐pH‐values, this value for (5) has increased to 0.92. The newly synthesized phthalocyanines are suitable photosensitizers for PDT applications, especially with high singlet oxygen quantum yield at pH 6.4.

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The new zinc phthalocyanine having high singlet oxygen quantum yield substituted with new benzenesulfonamide derivative groups containing schiff base

Cited by 24 publications

References 24 publications

Synthesis, Characterization and Photophysicochemical Properties of Zinc(Ii) Phthalocyanine With New Benzenesulfonamide Derivative Substituents

Synthesis, Characterization and Photophysicochemical Properties of Zinc(Ii) Phthalocyanine With New Benzenesulfonamide Derivative Substituents

Synthesis, spectroscopy, and photophysical properties of newly magnesium (II) phthalocyanine

Tumor‐pH‐value responsive non‐peripheral substituted phthalocyanines: Synthesis, investigation of photophysical and photochemical properties

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