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Preparing methods of tetraphenylethylene-based carboxylic acid organic ligand and complexes of ligand

A technology of tetrastyryl carboxylic acid and organic ligand, which is applied in the field of luminescent metal organic framework materials, can solve the problems of low yield and single ligand structure, and achieves simple method steps, simple synthesis method and good reproducibility. Effect

Inactive Publication Date: 2019-04-19
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the ligand structure of the above two luminescent materials is single and the yield is low.

Method used

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  • Preparing methods of tetraphenylethylene-based carboxylic acid organic ligand and complexes of ligand
  • Preparing methods of tetraphenylethylene-based carboxylic acid organic ligand and complexes of ligand
  • Preparing methods of tetraphenylethylene-based carboxylic acid organic ligand and complexes of ligand

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Experimental program
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Effect test

Embodiment 1

[0043] A kind of preparation method of tetrastyryl carboxylic acid organic ligand comprises the following steps:

[0044] (A) Synthesis of 3-methoxycarbonylphenylboronic acid ester: Add 5g of 3-carboxyphenylboronic acid, 75mL of methanol and 3mL of concentrated sulfuric acid with a concentration of 98wt% in a 250mL flask, reflux at 80°C for about 20h, take it out and cool it down to room temperature, add water Precipitation, standing for 1h, suction filtration, washing, and drying to obtain 3-methoxycarbonylphenyl borate;

[0045] (B) Synthesis of 1,1,2,2-tetra[(3-benzyloxycarbonyl)benzene]ethylene: 4g 3-methoxycarbonylphenylboronate, 1g 4Br-TPE and 0.47g tetrakistriphenylphosphine Mix the palladium evenly, vacuumize for 5 minutes and inflate with nitrogen for 3 times, inject 100mL of toluene ethanol solution with a volume ratio of 9:1 and 12mL of tripotassium phosphate solution with a concentration of 1mol / L, and reflux at 110°C for 24h until the raw materials are completely ...

Embodiment 2

[0052] A kind of preparation method of tetrastyryl carboxylic acid organic ligand comprises the following steps:

[0053] (A) Synthesis of 3-methoxycarbonylphenylboronic acid ester: Add 5g of 3-carboxyphenylboronic acid, 75mL of methanol and 3mL of concentrated sulfuric acid with a concentration of 98wt% in a 250mL flask, reflux at 80°C for about 20h, take it out and cool it down to room temperature, add water Precipitation, standing for 1h, suction filtration, washing, and drying to obtain 3-methoxycarbonylphenyl borate;

[0054] (B) Synthesis of 1,1,2,2-tetra[(3-benzyloxycarbonyl)benzene]ethylene: 4g 3-methoxycarbonylphenylboronate, 1g 4Br-TPE and 0.47g tetrakistriphenylphosphine Mix the palladium evenly, vacuumize for 5 minutes and inflate with nitrogen for 3 times, inject 100mL of toluene ethanol solution with a volume ratio of 9:1 and 12mL of tripotassium phosphate solution with a concentration of 1mol / L, and reflux at 110°C for 24h until the raw materials are completely ...

Embodiment 3

[0061] A kind of preparation method of tetrastyryl carboxylic acid organic ligand comprises the following steps:

[0062] (A) Synthesis of 3-methoxycarbonylphenylboronic acid ester: add 5g of 3-carboxyphenylboronic acid, 100mL of methanol and 5mL of 97wt% concentrated sulfuric acid in a 250mL flask, reflux at 90°C for about 12h, take it out and cool it down to room temperature, add water Precipitation, standing for 1h, suction filtration, washing, and drying to obtain 3-methoxycarbonylphenyl borate;

[0063] (B) Synthesis of 1,1,2,2-tetrakis[(3-benzyloxycarbonyl)benzene]ethylene: 4g 3-methoxycarbonylphenylboronate, 2g 4Br-TPE and 0.8g tetrakistriphenylphosphinepalladium Mix evenly, evacuate for 5 minutes and inflate with nitrogen for 3 times, inject 80 mL of toluene ethanol solution with a volume ratio of 9.5:1 and 8 mL of tripotassium phosphate solution with a concentration of 1.5 mol / L, and reflux at 120 ° C for 18 hours until the raw materials are completely reacted . Coo...

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Abstract

The invention relates to the technical field of light-emitting metal organic framework materials, and discloses preparing methods of a tetraphenylethylene-based carboxylic acid organic ligand and complexes of the ligand. The preparing methods of the organic ligand and the complexes of the ligand comprise the steps of synthesizing the tetraphenylethylene-based carboxylic acid organic ligand; conducting ultrasonic dissolution on metal salt, the tetraphenylethylene-based carboxylic acid organic ligand and N,N-dimethylformamide to obtain a mixed solution; conducting heat-preservation treatment onthe mixed solution, and conducting filtering to obtain a light-emitting organic framework compound. The novel organic ligand is synthesized. Compared with an organic ligand of a traditional para-position structure, the light-emitting metal organic framework structure constructed by the organic ligand is changeable, and therefore, the light-emitting metal organic framework complexes with differentproperties can be easily obtained. The yield of the synthesized ligand is high, and reaches 65%. The synthesis method of the complexes is simple, good in reproducibility, easy to operate and safe.

Description

technical field [0001] The invention relates to the technical field of luminescent metal organic framework materials, in particular to a preparation method of a tetrastyryl carboxylic acid organic ligand and a complex thereof. Background technique [0002] Luminescent metal-organic frameworks (LMOFs) are a class of luminescent open framework coordination polymers with potential gaps. This pathway emits strong fluorescence. The luminescent metal-organic frameworks currently being studied are mostly used in light-emitting applications, such as: chemical sensing, bioimaging and light-emitting devices. [0003] Tetraphenylethylene is a kind of organic ligand with simple structure, easy to modify, and strong luminescence in the aggregated state. The coordinating group on its aromatic ring can be used as a luminescent metal-organic framework ligand. "High-Performance Blue-Excitable Yellow Phosphor Obtained from an Activated Solvochromic Bismuth-Fluorophore Metal–Organic Framewor...

Claims

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Application Information

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IPC IPC(8): C07C51/02C07C51/09C07C63/331C07C67/343C07C69/78C07F5/02C07F3/02C07F13/00C09K11/06
CPCC07B2200/13C07C51/02C07C51/09C07C67/343C07F3/003C07F5/025C07F13/005C09K11/06C09K2211/188C07C63/331C07C69/78
Inventor 刘训高陶晨蕾徐媛张义建许波波王培
Owner HANGZHOU NORMAL UNIVERSITY
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