Fluorine pyridine fluorescent material and preparation method thereof

A fluorescent material, a technology of fluorenepyridine, applied in the field of fluorescent materials, can solve the problems of cumbersome synthesis steps, expensive preparation, harsh preparation conditions, etc., and achieve the effect of simple synthesis steps, high luminous efficiency, and high yield

Inactive Publication Date: 2014-07-16
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese patent 200910112709.X introduces an organic fluorescent material of glutamic acid derivatives, which emits blue fluorescence under ultraviolet light around 330nm, but its preparation conditions are relatively harsh
Chinese patent 200610124795.2 introduces an organic fluorescent material of pyridine derivatives, which can be used as a fluorescent probe in analysis and biochemistry, but it is a fluorescent composition material with rare earth metals, and the preparation price is relatively expensive
Chinese patent 200810162059.5 introduces an organic fluorescent material of naphthooxazole derivatives, which has a high fluorescence quantum yield, but its synthesis steps are cumbersome

Method used

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  • Fluorine pyridine fluorescent material and preparation method thereof
  • Fluorine pyridine fluorescent material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Get 2,7-dibromofluorene (2.0g 6.2mmol), 4-pyridine boronic acid (2.3g 18.6mmol), tetrakis triphenylphosphine palladium (0.21g0.186mmol), sodium carbonate (5.9g 55.8mmol) mixed in 150ml In the reaction device, the reaction device was evacuated and flushed with nitrogen three times, then a mixture of 50 ml of deoxygenated ethylene glycol dimethyl ether and 25 ml of water was added, and the reaction was carried out at 70° C. for 2 days under the protection of nitrogen. After the reaction was completed, it was extracted with dichloromethane, and the organic phases were combined and dried over magnesium sulfate to remove water. Use a rotary evaporator to remove dichloromethane and ethylene glycol dimethyl ether to obtain a solid powder, then use petroleum ether: ethyl acetate = 1:2 (volume ratio) eluent to separate through the column to obtain an organic compound of fluorenpyridine.

Embodiment 2

[0020] Get 2,7-dibromofluorene (2.0g 6.2mmol), 4-pyridine boronic acid (3.4g 27.9mmol), tetrakis triphenylphosphine palladium (0.21g0.186mmol), sodium carbonate (9g 83.6mmol) mixed in 150ml In the reaction device, the reaction device was vacuumed and flushed with nitrogen three times, then a mixture of 60 ml of deoxygenated ethylene glycol dimethyl ether and 30 ml of water was added, and the reaction was carried out at 80° C. for 3 days under the protection of nitrogen. After the reaction was completed, it was extracted with dichloromethane, and the organic phases were combined and dried over magnesium sulfate to remove water. Use a rotary evaporator to remove dichloromethane and ethylene glycol dimethyl ether to obtain a solid powder, then use petroleum ether: ethyl acetate = 1:2 (volume ratio) eluent to separate through the column to obtain an organic compound of fluorenpyridine.

Embodiment 3

[0022] Get 2,7-dibromofluorene (4.0g 12.4mmol), 4-pyridineboronic acid (4.6g 37.2mmol), tetrakistriphenylphosphine palladium (0.42g0.372mmol), sodium carbonate (11.8g 111.6mmol) mixed in 250ml In a three-necked flask, the reaction device was evacuated and flushed with nitrogen three times, then a mixture of 100 ml of deoxygenated ethylene glycol dimethyl ether and 50 ml of water was added, and the reaction was carried out at 95° C. for 3 days under the protection of nitrogen. After the reaction was completed, it was extracted with dichloromethane, and the organic phases were combined and dried over magnesium sulfate to remove water. Use a rotary evaporator to remove dichloromethane and ethylene glycol dimethyl ether to obtain a solid powder, then use petroleum ether: ethyl acetate = 1:2 (volume ratio) eluent to separate through the column to obtain an organic compound of fluorenpyridine.

[0023] The substances participating in the reaction in the above examples are all chemic...

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Abstract

The invention discloses a fluorine pyridine fluorescent material and a preparation method thereof. The invention is characterized in that the fluorescent material is a fluorine pyridine organic compound with a molecular formula of C23H16N2, a monocline crystal system, a P21 / c space group, and cell parameters: a=11.235Angstrom, b=24.361Angstrom, c=13.318Angstrom, alpha=gamma=90 degrees, and beta=113.13 degrees. The fluorescent material is prepared by a synthetic reaction of 2, 7-dibromofluorene, 4-pyridine boric acid, tetrakis(triphenylphosphine)palladium and sodium carbonate according to a certain ratio. The fluorine pyridine fluorescent material has a definite space structure and an accurate molecular formula, simple synthesis procedures, and high yield (up to 70-80%); and through the introduction of pyridyl groups at 2 and 7 sites, the electron cloud density of the material is increased, the stability and solubility property of the material are improved, the luminescence performance of the material is enhanced, and the luminous efficiency of the material is improved.

Description

technical field [0001] The invention relates to a fluorescent material, in particular to a fluorenepyridine fluorescent material and a preparation method thereof. Background technique [0002] Fluorescent materials usually refer to materials that can absorb and store energy after receiving external energy, and convert it into light energy in a dark place. It first came out in 1938. In the early days, Stokes et al. synthesized phosphors such as calcium tungstate and used them in fluorescent lamps. Phosphate phosphor was developed in 1948, and the luminous performance of this phosphor has been significantly improved compared with the early phosphor. Phosphor powder was widely used in the 1960s and 1970s. Introducing optically active metal ions or organic ligands containing conjugated units into fluorescent materials can greatly improve the luminescent properties of fluorescent materials. Compounds with strong fluorescent light-emitting ability have very important potential...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07D213/127
Inventor 李星刘志鹏潘炜
Owner NINGBO UNIV
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