Mixed-ligand Zn(II) complexes of 1-phenyl-3-methyl-4-formylpyrazole-5-one and various aminoheterocycles: Synthesis, structure and photoluminescence properties

Бурлов, А. С.; Koshchienko, Yu. V.; Макарова, Н. И.; Кузьменко, Т. А.; Chesnokov, V. V.; Кискин, М. А.; Николаевский, С. А.; Гарновский, Д. А.; Ураев, А. И.; Власенко, В. Г.; Метелица, А. В.

doi:10.1016/j.synthmet.2016.06.025

Cited by 26 publications

(8 citation statements)

References 31 publications

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“…Particularly, the highest quantum yields was found for of 4 while lowest—for 7. It is well known that zinc cations in complexes play a key role in increasing the fluorescent emission due to enhancement in the rigidity of the ligand and reduces the loss of energy by thermal vibrational decay, contributing to an increase in the lifetime of the excited state and efficiency of luminescence [ 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 ]. To support this, the luminescence decay curves for both ligands and their corresponding complexes were recorded at room temperature in the solid state.…”

Section: Resultsmentioning

confidence: 99%

“…Among the promising optical materials, zinc complexes have been especially important because of the simplicity in their synthesis procedures, wide range of emission maximum position and low cost of zinc in comparison with platinum metals and f-elements. Extensive research work in recent decades has led to the preparation of a number of new zinc complexes containing organic ligands [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 ], which have been used as emitters and electron transporters in OLED research. The molecular design and synthesis of new organic ligands are among the main approaches for the construction of zinc complexes with controllable luminescent properties.…”

Section: Introductionmentioning

confidence: 99%

“…The molecular design and synthesis of new organic ligands are among the main approaches for the construction of zinc complexes with controllable luminescent properties. Among the large number of zinc complexes azomethine ligands proved to be excellent candidates for the development of new luminescent material due to the ease of introduction and targeted variation of type and position of substituents [ 16 , 17 , 18 , 19 , 20 , 21 ].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Photoluminescence and Electrical Study of Pyrazolone-Based Azomethine Ligand Zn(II) Complexes

Гусев¹,

Braga²,

Tyutyunik³

et al. 2020

Materials

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New luminescent zinc complexes were obtained by reaction of pyrazolone-based azomethine ligands with Zn(CH3COO)2·2H2O. Complexes fully characterized by elemental analysis, FTIR, ES–MS, NMR, and single crystal X-ray analysis. Title complexes in the solid state demonstrate tunable luminescence from blue to orange by varying of substituents on the aromatic ring. Quantum yields are in the 0.03 to 0.49 range. TGA data shows that obtained complexes demonstrate high thermal stability and can be used as electroluminescent materials. The electrical properties of the complexes under study were considered in the ITO-Zncomplex-Al “sandwich” structure.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Photoluminescence and Electrical Study of Pyrazolone-Based Azomethine Ligand Zn(II) Complexes

Гусев¹,

Braga²,

Tyutyunik³

et al. 2020

Materials

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“…We previously reported on molecular adducts of zinc(II) chelate based on 1‐pheny‐3‐methyl‐4‐formylpyrazol‐5‐one (as a β ‐diketonate‐like ligand) with various aminoquinolines, which have photo‐ and electroluminescence with high quantum yields . In these molecular systems, aminoquinoline moieties act as emitters, while zinc formylpyrazolonate part is responsible for thermal and chemical stability.…”

Section: Figurementioning

confidence: 99%

“…In the literature, there is no information about 2‐AQ and 4‐AQ adducts similar to 1 a,b . Compared with the previously obtained luminescent adducts of 6‐AQ and 5‐ADQ with zinc(II) formylpyrazolonate, the luminescence band maximum of compounds 1 c,d is shifted to the blue region by 37 and 25 nm, respectively. Fluorescence quantum yields ϕ of zinc acetylacetonate adducts 1 c and 1 d are slightly inferior to the quantum yields of formylpyrazolone analogues (0.40 and 0.37 versus 0.55 and 0.36).…”

Section: Figurementioning

confidence: 99%

Adducts of Zinc(II) Acetylacetonate with Various Aminoquinolines: Synthesis, Structure and Luminescence

Chesnokov

Ростовцева

2019

ChemistrySelect

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New adducts of zinc(II) acetylacetonate of composition [Zn(acac)2L] (where L=2‐aminoquinoline, 4‐aminoquinoline, 6‐aminoquinoline, 5‐amino‐4,6‐dimethylquinoline) were obtained and characterized by elemental analysis, IR and 1H‐NMR. The optical properties of zinc(II) adducts were investigated by UV/Vis and photoluminescence spectroscopy. In these adducts, each zinc(II) ion is coordinated with two acetylacetonate moieties and one aminoquinoline ligand through an endocyclic nitrogen atom. Adducts show thermal stability (m.p.>180 °C), good solubility in non‐polar solvents, but they easily decompose in the presence of Lewis bases. The 4‐aminoquinoline adduct does not luminesce. The emission bands of other compounds in CH2Cl2 solutions are located in the blue region of the spectrum in the range 373–460 nm with quantum yields ϕ= 0.21‐0.40.

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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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Mixed-ligand Zn(II) complexes of 1-phenyl-3-methyl-4-formylpyrazole-5-one and various aminoheterocycles: Synthesis, structure and photoluminescence properties

Cited by 26 publications

References 31 publications

Synthesis, Photoluminescence and Electrical Study of Pyrazolone-Based Azomethine Ligand Zn(II) Complexes

Synthesis, Photoluminescence and Electrical Study of Pyrazolone-Based Azomethine Ligand Zn(II) Complexes

Adducts of Zinc(II) Acetylacetonate with Various Aminoquinolines: Synthesis, Structure and Luminescence

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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