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Method for preparing chiral dual-core europium beta-diketone complex luminescent material

A technology of luminescent materials and complexes, which is applied in the direction of luminescent materials, chemical instruments and methods, and compounds containing elements of group 3/13 of the periodic table, etc. It can solve the problem of patent reports on chiral dinuclear rare earth β-diketone compounds, etc. problem, to achieve high yield, good reproducibility, and enhanced luminescent performance

Active Publication Date: 2014-07-02
郑州轻大产业技术研究院有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The chiral europium β-diketone complexes that have been reported are all mononuclear compounds, and there are no related patent reports on chiral dinuclear rare earth β-diketone compounds

Method used

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  • Method for preparing chiral dual-core europium beta-diketone complex luminescent material
  • Method for preparing chiral dual-core europium beta-diketone complex luminescent material
  • Method for preparing chiral dual-core europium beta-diketone complex luminescent material

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Embodiment 1

[0028] A preparation method of a chiral dinuclear europium β-diketone complex luminescent material is as follows: firstly prepare a chiral pinene pyridine pyrazine derivative organic bridging ligand (–)-2,5-bis(4,5-pine En-2-pyridyl), the preparation steps are as follows:

[0029] (1) Synthesis of 2,5-diformylpyrazine

[0030] Add 0.01 mmol pyrazine to the reaction vessel, then add 0.02 mmol acetaldehyde, 15 mL water, 15 mL glacial acetic acid and 3 mL concentrated sulfuric acid, keep the reaction temperature at 0°C, stir for 15 minutes, then slowly add 0.02 mmol tert-butyl After the dropwise addition, continue to stir for 20 minutes, and finally slowly add 1 mL of ferrous sulfate aqueous solution with a concentration of 0.02~0.04 mol / L. After the dropwise addition, continue to stir for 2 hours, filter and wash with water to obtain light yellow Powder, namely 2,5-diformylpyrazine;

[0031] (2) Synthesis of 2,5-diformylpyrazine pyridinium iodide salt

[0032] Add 76 mmol iod...

Embodiment 2

[0037] A preparation method of a chiral dinuclear europium β-diketone complex luminescent material is as follows: firstly prepare a chiral pinene pyridine pyrazine derivative organic bridging ligand (–)-2,5-bis(4,5-pine En-2-pyridyl), the preparation steps are as follows:

[0038] (1) Synthesis of 2,5-diformylpyrazine

[0039] Add 0.02 mmol pyrazine to the reaction vessel, then add 0.04 mmol acetaldehyde, 20 mL water, 20 mL glacial acetic acid and 4 mL concentrated sulfuric acid, keep the reaction temperature at 0°C, stir for 20 minutes, then slowly add 0.04 mmol tert-butyl After the dropwise addition, continue to stir for 30 minutes, and finally slowly add 1 mL of ferrous sulfate aqueous solution with a concentration of 0.04 mol / L. After the dropwise addition, continue to stir for 3 hours, filter and wash with water to obtain a light yellow powder. That is, 2,5-diformylpyrazine;

[0040] (2) Synthesis of 2,5-diformylpyrazine pyridinium iodide salt

[0041] Add 80 mmol iodi...

Embodiment 3

[0046] A preparation method of a chiral dinuclear europium β-diketone complex luminescent material is as follows: firstly prepare a chiral pinene pyridine pyrazine derivative organic bridging ligand (–)-2,5-bis(4,5-pine En-2-pyridyl), the preparation steps are as follows:

[0047] (1) Synthesis of 2,5-diformylpyrazine

[0048] Add 0.015 mmol of pyrazine to the reaction vessel, then add 0.03 mmol of acetaldehyde, 18 mL of water, 18 mL of glacial acetic acid and 4 mL of concentrated sulfuric acid, keep the reaction temperature at 0°C, stir for 18 minutes, then slowly add 0.03 mmol of tert-butyl Base hydrogen peroxide, continue to stir for 25 minutes after the dropwise addition, and finally slowly dropwise add 1 mL of ferrous sulfate aqueous solution with a concentration of 0.03 mol / L, continue to stir for 2.5 hours after the dropwise addition, filter and wash with water to obtain a light yellow powder. That is, 2,5-diformylpyrazine;

[0049] (2) Synthesis of 2,5-diformylpyrazi...

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Abstract

The invention discloses a method for preparing a chiral dual-core europium beta-diketone complex luminescent material. The method comprises the following steps: dissolving Eu(tta)3.2H2O into ethanol to prepare a solution a of which the concentration is 0.01mol / L at normal temperature; dissolving an organic bridging ligand (-)-2,5-bi(4,5-pinene-2-pyridyl) of chiral pinene pyridine pyrazine derivatives into acetone to prepare a solution b of which the concentration is 0.005mol / L; mixing the solution a with the solution b at equal volume and then agitating for 20 minutes; standing the mixed solution; filtering after 6-8 days; and washing by using absolute ether and drying in vacuum, so as to prepare the chiral dual-core europium beta-diketone complex luminescent material. The luminescent material is mild in synthesis condition, high in yield, strong in stability, and easy to separate and purify, and is expected to have a broad application prospect in the aspects such as an electroluminescent device, a bioluminescent probe, a nonlinear optical material and a light conversion molecular device as a novel luminescent material.

Description

technical field [0001] The invention belongs to the technical field of inorganic-organic hybrid rare earth functional materials and preparation thereof, in particular to a preparation method of a chiral dinuclear europium crystalline material with strong luminescence. Background technique [0002] Due to the special configuration of the f electron shell of rare earth europium ions, the complexes of europium have red light emitting properties in the visible light range, and the emitted red light has high color purity and long life. These unique photophysical properties make europium complexes have broad application prospects as luminescent materials in electroluminescent devices, lasers, bioluminescent probes, and photoconverting molecular devices. However, the molar absorption coefficient of europium ion itself is very low, and its absorption ability to ultraviolet and visible light is weak. Therefore, to prepare europium complexes with strong luminescent properties, organic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/00C07D401/14C09K11/06
Inventor 李郤里周立明李彩凤高丽君方少明
Owner 郑州轻大产业技术研究院有限公司
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