Synthesis, characterization, luminescent properties and biological activities of zinc complexes with bidentate azomethine Schiff-base ligands

Бурлов, А. С.; Власенко, В. Г.; Koshchienko, Yu. V.; Макарова, Н. И.; Зубенко, А. А.; Drobin, Yu.D.; Фетисов, Л. Н.; Колодина, А. А.; Zubavichus, Ya. V.; Trigub, Alexander L.; Левченков, С. И.; Гарновский, Д. А.

doi:10.1016/j.poly.2018.07.034

Cited by 49 publications

(23 citation statements)

References 36 publications

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“…The synthetic pathways for the synthesis of corresponding compounds were given (3,5,7,9) in Schemes 1 and 2 (11,12). The treatment of 4-amino-1,-5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…The treatment of indole-3-carbaldehyde (2) with trans-cyclohexane-1,2-diamine (10) in ethanol at 80 C yielded the (1S,2S,N1,N2)-N1,N2-bis((1H-indol-3-yl) methylene)cyclohexane-1,2-diamine (11). In the IR spectrum, the NH vibration band was observed at 2,925 cm −1 .…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…Three new (5,11,12) and three known (3, 7, 9) SBs were synthesized efficiently in high yields. The addition of aldehyde slowly into the reaction medium is important for product yield.…”

Section: Reducing Powermentioning

confidence: 99%

“…[ 9 ] Due to the electron‐donating ability, SBs could be used in the field of coordination chemistry extensively. [ 10 ] SBs are among the most chiefly used organic compounds, revealing a wide range of applications, such as electroluminescent effects, [ 11 ] fluorescence properties, [ 12 ] nonlinear optical properties, [ 13 ] chemosensory. [ 14 ] In addition, SBs and their metal complexes have showed a large variety of biological activity in recent research, including anticancer, antioxidant, [ 15 ] antibacterial, antibiofilm, anti‐inflammatory, hemocompatibility, cytotoxic, [ 16 ] pesticidal, nematicidal activities.…”

Section: Introductionmentioning

confidence: 99%

“…13 C NMR (100 MHz, CDCl 3 ) δ: 159.6, 156.8, 154.4, 152.9, 148.0, 136.8, 134.8, 130.4, 129.7, 129.5, 128.5, 128.4, 127.9, 127.6, 125.8, 117.6, 115.9, 35.4, 10.2 (Figure S17). Synthesis of (1S,2S,N1,N2)-N1,N2bis((1H-indol-3-yl)methylene)cyclohexane-1,2-diamine(11)…”

mentioning

confidence: 99%

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Synthesis, characterization, and antioxidant activity of heterocyclic Schiff bases

Kızılkaya

Dağ

Aral

et al. 2020

J Chinese Chemical Soc

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Schiff base derivatives have gained great importance due to revealing a great number of biological properties. Schiff bases were synthesized by treatment of 4-amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (1) with various aldehydes in methanol at reflux. In addition, diamine was reacted with an aldehyde to yield the corresponding Schiff bases. The structures of synthesized Schiff bases were elucidated by spectroscopic methods such as microanalysis, 1 H-NMR, 13 C-NMR, and FTIR. Antioxidant activities of synthesized Schiff bases were carried out using different antioxidant assays such as 1,1-diphenyl-2-picryl-hydrazyl free radical (DPPH •) scavenging, 2,2 0-azino-bis (3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical scavenging, and reducing power activity. (E)-4-((1H-indol-3-yl)methyleneamino)-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (3), (E)-1,5-dimethyl-4-((2-methyl-1H-indol-3-yl) methyleneamino)-2-phenyl-1H-pyrazol-3(2H)-one (5), (E)-1,5-dimethyl-2-phenyl-4-(thiophen-2-ylmethyleneamino)-1H-pyrazol-3(2H)-one (7), (E)-1,5-dimethyl-2-phenyl-4-(quinolin-2-ylmethyleneamino)-1H-pyrazol-3(2H)-one (9), (1S,2S, N1,N2)-N1,N2-bis((1H-indol-3-yl)methylene)cyclohexane-1,2-diamine (11), and (1S,2S,N1,N2)-N1,N2-bis((2-methyl-1H-indol-3-yl)methylene)cyclohexane-1,2-diamine (12) were synthesized in high yields. Compound 5 displayed a good ABTS •+ activity. Compound 3 revealed the outstanding activity in all assays. Compound 7 has the best-reducing power ability in comparison to other synthesized compounds. Although compounds 5, 11, 12 are new, compounds 3, 7, 9 are known. Due to revealing a good antioxidant activity, the synthesized compounds (3, 5, 7) have the potential to be used as synthetic antioxidant agents.

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“…The synthetic pathways for the synthesis of corresponding compounds were given (3,5,7,9) in Schemes 1 and 2 (11,12). The treatment of 4-amino-1,-5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…Three new (5,11,12) and three known (3, 7, 9) SBs were synthesized efficiently in high yields. The addition of aldehyde slowly into the reaction medium is important for product yield.…”

Section: Reducing Powermentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Synthesis, characterization, and antioxidant activity of heterocyclic Schiff bases

Kızılkaya

Dağ

Aral

et al. 2020

J Chinese Chemical Soc

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Chemical and electrochemical synthesis, structure, photoluminescent properties, and biological activity of 4‐methyl‐N‐[2‐[(Z)‐2‐(2‐pyridyl)alkyliminomethyl]phenyl]benzenesulfamide zinc(II) complexes

Бурлов

Власенко

Koshchienko

et al. 2019

Applied Organom Chemis

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A series of Zn(II) complexes of the tridentate azomethine ligands, condensation products of 2‐(N‐tosylamino)benzaldehyde and 2‐aminoalkylpyridines, were synthesized by chemical and electrochemical methods. All compounds were characterized on the basis of C, H, N elemental analysis, Fourier‐transform infrared, 1H nuclear magnetic resonance, UV–Vis, and photoluminescence studies. The local atomic structures of complexes were determined from analysis of extended X‐ray absorption fine structure and X‐ray absorption near‐edge structure of Zn K‐edges. The molecular structure of chloro‐{4‐methyl‐N‐[2‐[(Z)‐2‐pyridyl)ethyliminomethyl]phenyl]benzenesulfamide}zinc(II) was determined by X‐ray single‐crystal diffraction. The fluorescence spectra show that these complexes in dimethyl sulfoxide solutions at room temperature emit bright blue luminescence at 435–461 nm with fluorescence quantum yields in the range of 0.20–0.31. The assignment and the nature of the bands in experimental UV–Vis spectra of complexes were analyzed using time‐dependent density functional theory calculations B3LYP/6‐31G(d). The azomethines and complexes of zinc have been screened for their antibacterial, protistocidal, and fungistatic activities against Penicillium italicum, Colpoda steinii, Escherichia coli 078, and Staphylococcus aureus P‐209, and the results are compared with the activity of furazolidone, chloroquine, and Fundazol.

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Zinc (II) complexes with Schiff bases obtained from N‐[2‐(cyclohexyliminomethyl)‐ or 2‐(4‐cyclohexylphenyliminomethyl) phenyl]‐4‐methylbenzenesulfonamides and their application as highly luminescent blue emitters for OLEDs

Burlov,

Koshchienko,

Vlasenko

et al. 2024

Applied Organom Chemis

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Two new Schiff base compounds of N‐{2‐[(E)‐сyclohexyliminomethyl]phenyl}‐4‐methylbenzenesulfonamide, N‐{2‐[(E)‐(4‐сyclohexylphenyl)iminomethyl]phenyl}‐4‐methylbenzenesulfonamide and their Zn(II) complexes have been synthesized and characterized by elemental analysis, FT‐IR and UV–Vis spectra, and single crystal X‐ray determination. In both complexes, Zn2+ ions have a tetrahedral environment with two nitrogen atoms of the tosylamide groups and two nitrogen atoms of the imine fragment. Time‐dependent density functional theory calculations have been performed on two zinc(II) complexes in order to assign their experimental UV–visible absorption bands. Zinc(II) complexes showed thermal stability up to 335–340°C under a nitrogen atmosphere by thermogravimetric analysis (TGA). The photoluminescent spectra show that both Zn(II) complexes in the solid state at room temperature emit blue luminescence with high emission quantum yields of 20% and 29%. The doped devices with configurations of indium tin oxide (ITO)/poly(3,4‐ethylenedioxythiophene):poly(styrene sulfonate) (PEDOT:PSS)/N,N′‐Di(1‐naphthyl)‐N,N′‐diphenyl‐(1,1′‐biphenyl)‐4,4′‐diamine (NPD)/4,4′‐N,N′ ‐dicarbazolebiphenyl (CBP):Zinc(II) complex (5%)/1,3,5‐tris(N‐phenylbenzimidazole‐2‐yl) benzene (TPBI)/LiF/Al have been fabricated and investigated. The doped device based on the complex with the сyclohexylphenyl substituent of the ligand showed the best electroluminescent characteristics with maximum brightness Lmax of 3415 cd/m2, maximum current efficiency of 2.8 cd/A, and power efficiency of 1.9 lm/W, while the doped device with emitter on the base of the complex with the сyclohexyl substituent showed slightly worse electroluminescence (EL) performance with Lmax of 2105 cd/m2, maximum current efficiency of 2.1 cd/A, and power efficiency of 1.6 lm/W.

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Synthesis, characterization, luminescent properties and biological activities of zinc complexes with bidentate azomethine Schiff-base ligands

Cited by 49 publications

References 36 publications

Synthesis, characterization, and antioxidant activity of heterocyclic Schiff bases

Synthesis, characterization, and antioxidant activity of heterocyclic Schiff bases

Chemical and electrochemical synthesis, structure, photoluminescent properties, and biological activity of 4‐methyl‐N‐[2‐[(Z)‐2‐(2‐pyridyl)alkyliminomethyl]phenyl]benzenesulfamide zinc(II) complexes

Zinc (II) complexes with Schiff bases obtained from N‐[2‐(cyclohexyliminomethyl)‐ or 2‐(4‐cyclohexylphenyliminomethyl) phenyl]‐4‐methylbenzenesulfonamides and their application as highly luminescent blue emitters for OLEDs

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