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Methacrylate fluorescent monomer with thiazolepyridine structure and preparation method thereof

A methacrylate and thiazopyridone-containing technology, which is applied in the field of fluorescent compound synthesis, can solve problems such as the difficulty in synthesizing fluorescent polymers with a high degree of polymerization, the quantum yield being easily affected by solvents, and the free radical polymerization process. Achieve the effect of mass production, high quantum yield, and small steric hindrance

Active Publication Date: 2016-03-23
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The synthesis of fluorescent polymers usually requires polymerizable fluorescent monomers, and there are some problems in the research on the latter: 1) Most fluorescent compounds are conjugated organic molecules, which are difficult to dissolve in water and complex to synthesize, making it difficult to popularize and apply
2) Even if fluorescent molecules are bonded to hydrophilic polymer chains, their quantum yields are easily affected by solvents and are generally lower in water
3) Olefin monomers constructed by conjugated organic molecules have a large steric hindrance, which is easy to affect the free radical polymerization process, and it is difficult to synthesize fluorescent polymers with high polymerization degrees

Method used

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  • Methacrylate fluorescent monomer with thiazolepyridine structure and preparation method thereof
  • Methacrylate fluorescent monomer with thiazolepyridine structure and preparation method thereof
  • Methacrylate fluorescent monomer with thiazolepyridine structure and preparation method thereof

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Embodiment 1

[0028] A preparation method of a methacrylate fluorescent monomer containing a thiazopyridone structure is as follows: weigh 1.95g thiazopyridone-3-carboxylic acid, 2.00mL hydroxyethyl methacrylate, 3.82g 1-ethyl-(3 -Dimethylaminopropyl) carbodiimide hydrochloride, 2.70g of 1-hydroxybenzotriazole and 6.50mL of triethylamine were dissolved in 60mL of N,N-dimethylformamide, under nitrogen protection conditions Stir the reaction at room temperature 20°C for 48 hours, then filter the mixture under reduced pressure after the reaction, add an equal volume of deionized water to the obtained filtrate and dilute with ethyl acetate three times, take the upper organic phase and use the mass fraction Repeatedly washing with 10% citric acid aqueous solution and saturated sodium bicarbonate solution, then drying and rotating the solvent to obtain a crystal methacrylate fluorescent monomer containing a thiazopyridone structure.

Embodiment 2

[0030] A preparation method of a methacrylate fluorescent monomer containing a thiazopyridone structure is as follows: weigh 4.00g thiazopyridone-3-carboxylic acid, 4.00mL hydroxyethyl methacrylate, 8.00g1-ethyl-(3 -Dimethylaminopropyl) carbodiimide hydrochloride, 5.50g of 1-hydroxybenzotriazole and 13.00mL of triethylamine were dissolved in 150mL of dimethyl sulfoxide, under nitrogen protection conditions at room temperature for 20 The reaction was stirred at °C for 24 hours. Then the mixture after the reaction was filtered under reduced pressure, added a sufficient amount of deionized water to the resulting filtrate to dilute and extracted three times with dichloromethane, and the upper organic phase was repeated with 10% hydrochloric acid and saturated sodium bicarbonate solution After washing, drying and rotary evaporation of the solvent, a crystal methacrylate fluorescent monomer containing a thiazopyridone structure is obtained.

[0031] see figure 1 , the structure of...

Embodiment 3

[0033] A preparation method of a methacrylate fluorescent monomer containing a thiazopyridone structure is: under stirring, thiazopyridone-3-carboxylic acid, methacrylic acid hydroxyl Ethyl ester, 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, 1-hydroxybenzotriazole and triethylamine were dissolved in water, and then heated at 40°C under nitrogen protection After reacting for 24 hours, the reaction product was purified. The specific process of purification was as follows: filter the mixture after the reaction under reduced pressure, add deionized water equal to the volume of the filtrate to dilute the resulting filtrate, and extract the polysaccharide with ethyl acetate. Once, the upper organic phase was repeatedly washed with 1% citric acid aqueous solution and saturated sodium bicarbonate solution, then dried and the solvent was rotated to obtain a methacrylate fluorescent monomer containing a thiazopyridone structure. Wherein, the mass ratio of water to thiazop...

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Abstract

A methacrylate fluorescent monomer with thiazolepyridine structure and a preparation method thereof are disclosed. The methacrylate fluorescent monomer with the thiazolepyridine structure is prepared using thiazolepyridine-3-carboxyl and hydroxyethyl methacrylate as starting materials or thiazolepyridine-3,7-dicarboxyl and hydroxyethyl methacrylate as starting materials. A synthetic method of the invention has few side products, the prepared methacrylate fluorescent monomer is high in product purity and high in quantum yield, the synthetic method is simple to operate, has mild reaction conditions and allows large-scale preparation and easy industrialization, and fluorescent polymers are easy to prepare through polymerization reaction.

Description

technical field [0001] The invention belongs to the technical field of fluorescent compound synthesis, and in particular relates to a methacrylate fluorescent monomer containing a thiazopyridone structure and a preparation method thereof. Background technique [0002] After the fluorescent compound is excited by ultraviolet light, electricity or chemical energy, the electrons transition from the ground state to the excited state, and then release photons through radiative decay to return to the ground state and generate fluorescence. The application of fluorescent compounds has penetrated into biomedical fields such as biosensing, bioimaging, and photodynamic therapy, as well as the fields of three-dimensional information storage and microprocessing. [0003] On the other hand, with the emergence of new reactions and new polymerization methods, such as click chemistry (Click) reaction, atom transfer radical polymerization (ATRP), nitrogen-oxygen stabilized radical polymeriza...

Claims

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Application Information

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IPC IPC(8): C07D513/04C09K11/06
CPCC09K11/06C07D513/04C09K2211/1037
Inventor 杨建海谢若森陈咏梅
Owner XI AN JIAOTONG UNIV
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