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Preparation method and application of 8-hydroxyquinoline complexes with four-core structures

A technology of hydroxyquinoline and complexes, applied in the field of metal-organic coordination chemistry, can solve the problems that the luminous intensity and quantum yield of the device cannot reach the practical stage, hinder the controllable structure and good luminous performance, and low cost, and achieve Broad commercialization prospects, large-scale production, and low-cost effects

Inactive Publication Date: 2018-06-08
ANHUI UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

In recent years, the structure of 8-hydroxyquinoline metal complexes synthesized by people is mainly mononuclear Mq n type, however, Mq n The luminous intensity and quantum yield of devices made of new-type luminescent materials still cannot reach the practical stage, and mononuclear metal-organic complexes limit or even hinder the preparation of new 8-hydroxyquinoline metal-organic materials with controllable structures and good luminescent properties. , in order to further regulate and optimize the emission wavelength, lifetime and quantum yield of 8-hydroxyquinoline metal complexes, develop new synthetic methods and strategies to obtain 8-hydroxyquinoline with clear structure, low cost and good luminescence performance The polynuclear metal-organic complexes of morphines are of great significance

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  • Preparation method and application of 8-hydroxyquinoline complexes with four-core structures
  • Preparation method and application of 8-hydroxyquinoline complexes with four-core structures
  • Preparation method and application of 8-hydroxyquinoline complexes with four-core structures

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preparation example Construction

[0033] The present invention also provides a method for preparing the above-mentioned 8-hydroxyquinoline aluminum and gallium complex with a tetranuclear structure, wherein the preparation method comprises: an organic ligand with a structure of formula (II), a metal salt (aluminum salt or gallium salt) aqueous solution and organic solvent are mixed and reacted to prepare two crystalline complexes of structure (I).

[0034]

[0035] In the reaction of preparing the two crystalline complexes of the structure (I), the source of the organic ligand using the structure of the formula (II) is not particularly limited, it can be purchased or made by itself according to the existing literature, and the metal salt is preferably Aluminum nitrate and gallium nitrate, the concentration of the metal salt solution is preferably 0.02 to 0.1mol / L, more preferably 0.08mol / L; the organic solvent is preferably N,N-dimethylformamide and methanol; the The volume ratio of the organic solvent N,N-...

Embodiment 1

[0041] The preparation of formula (II) compound: take by weighing 8-hydroxyquinaldine (10mmol), m-phthalaldehyde (5mmol) in the 25mL double-necked round-bottomed flask of oven dry, add acetic anhydride (10mL) in reaction bottle, N 2 Under protection, it was heated to 120°C for 72h. After cooling to room temperature, a yellow solid was obtained, which was washed three times with distilled water and dried to obtain the target product, yield: 2.05 g, 82%. Dissolve (E,E')-2,2-(1,3-divinylphenyl)bis-8-acetoxyquinaldine (2.0 g, 4 mmol) obtained above in 60 mL of pyridine, Then, 15 mL of distilled water was added to the reaction flask, heated to reflux, and reacted overnight. Cool to room temperature, remove pyridine by distillation under reduced pressure, add 200 mL of distilled water, filter to obtain a yellow solid, wash with distilled water, and dry in vacuo to obtain the target product (E,E')-2,2-(1,3-divinylphenyl) Bis-8-hydroxyquinoline. Yield 1.4g, 84%. 1 HNMR (DMSO-d 6...

Embodiment 2

[0043] Synthesis of 8-hydroxyquinoline aluminum complex (1) shown in formula (I): (E, E')-2,2-(1,3-divinylphenyl) bis-8-hydroxyquinoline (10mmol) was dissolved in N,N-dimethylformamide and methanol mixed solvent (12mL, V / V=1:5), Al(NO 3 ) 3 9H 2 O (20mmol) aqueous solution (0.08mol / L) was added dropwise in the solution, the mixed solution was sealed in a 80mL reactor, kept at 70°C for 20 hours, filtered to obtain yellow blocky crystals, washed with methanol and ether and placed in Air dry. Yield 5.45 g, 85%. ESI-MS m / z: 1537 ([M+1] + );C 88 h 68 o 12 N 6 Al 4 Elemental Analysis Calculated: C70.02, H 4.54, N 5.57; Found: C 69.98, H 4.48, N 5.54. FTIR (KBr tablet): 3443.64(s), 2836.42(w), 1669.54(w), 1599.93(m), 1558.08(s), 1505.81(s), 1455.43(s), 1384.61(s), 1344.48(m ), 1307.51(m), 1279.84(w), 1163.43(w), 1106.94(s), 1059.35(w), 969.55(m), 886.40(w), 832.04(m), 804.50(w), 753.91(s ), 700.06(w), 666.55(w).

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Abstract

The invention discloses a preparation method and application of 8-hydroxyquinoline complexes with four-core structures and belongs to the technical field of metal-organic coordination chemistry. The preparation method disclosed by the invention comprises the following specific steps: dissolving an organic ligand (E,E')-2,2-(1,3-divinyl phenyl)bi-8-acetoxyquinaldine into N,N-dimethylformamide and methanol; then adding metallic aluminum or an aqueous solution of gallium salt, putting the obtained mixed solution into a sealed container, and reacting at the temperature of 30 to 80 DEG C until a crystalline product separates out; washing a product with the methanol and drying. The two 8-hydroxyquinoline complexes prepared by the preparation method disclosed by the invention have good fluorescence properties and have potential economic value in the application aspects of preparing luminescent devices and the like. Besides, the preparation method of a luminous material, provided by the invention, has the advantages of simplicity, wide source of raw materials, capability of realizing large-scale production and broad commercial prospect.

Description

technical field [0001] The invention belongs to the field of metal-organic coordination chemistry, and specifically relates to the preparation method and application of two kinds of 8-hydroxyquinoline aluminum and gallium complexes with tetranuclear structures. Background technique [0002] At present, luminescent materials are mainly divided into inorganic materials, organic materials and metal-organic complex materials. Organic and inorganic light-emitting materials have shown broad application prospects in lighting, displays, molecular sensing, and optical devices. Some inorganic light-emitting materials (such as BaMgAl 10 o 17 :Eu 2+ and GdMgB 5 o 10 : Ce 3+ , Tb 3+ ) have even been transformed into commercial products. Phosphors have the advantages of narrow emission spectrum, bright colors, strong light absorption ability, and high conversion efficiency; on the other hand, their luminescence properties are usually affected by atomic structure, composition, partic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/06C07F5/00C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07F5/003C07F5/069C07B2200/13C09K2211/188C09K2211/186H10K85/326H10K85/324H10K50/11
Inventor 袁国赞赵祥祥汪世林
Owner ANHUI UNIVERSITY OF TECHNOLOGY
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