A kind of barbituric acid derivative and its preparation method and application

A technology of barbituric acid and diphenylbarbituric acid, which is applied in the field of fluorescence detection, can solve the problems of limited detection of nitroaromatics and poor solubility, and achieve obvious fluorescence quenching phenomenon, low detection limit and high sensitivity Effect

Active Publication Date: 2021-02-23
山东胜利生物工程有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Fluorescence sensing method has advantages in the detection of trace amounts of nitroaromatic explosives, but due to the poor solubility of most fluorescent substances in water, the detection of nitroaromatics in sewage is greatly limited by fluorescence sensing technology.

Method used

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  • A kind of barbituric acid derivative and its preparation method and application
  • A kind of barbituric acid derivative and its preparation method and application
  • A kind of barbituric acid derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The synthesis of 4-(diphenylamino)-benzaldehyde, the route is as follows:

[0058]

[0059] At 0°C, 2 mL of anhydrous (N,N-dimethylformamide) DMF (25.7 mmol) was added to 5 mL of phosphorus oxychloride (POCl 3 ) (54mmol) and held for 15 minutes, then triphenylamine (1 g, 4mmol) was added with stirring. The mixture was heated to 45°C for 2.5 hours. After cooling, the clear red solution was dropped into ice water. The resulting mixture was filtered, washed and redissolved in dichloromethane. The solution was washed with water (150 mL) and dried over magnesium sulfate. After evaporation of the solvent, column chromatography gave the pure product, ie, 4-(dianilino)-benzaldehyde. Yield: 0.78 g (80%). 1 H NMR (400MHz, CDCI 3 ):δ9.82(s,1H),7.74–7.61(m,2H),7.35(t,J=7.7Hz,4H),7.22–7.13(m,6H),7.07–6.96(m,2H).

Embodiment 2

[0061] The synthesis of 1,3-diphenylbarbituric acid is as follows:

[0062]

[0063] Malonyl chloride (33.3 mg, 2 mmol) was added to a solution containing 6 ml of CHCl 3 N,N-diphenylurea (424.5mg, 2mmol), and the mixture was heated to 80°C for 4 hours. Then the reaction mixture was extracted with dichloromethane, and the 2 SO 4 Dry on top. After filtration, the filtrate was concentrated under reduced pressure and further purified by column chromatography to obtain 1,3-diphenylbarbituric acid. Yield: 343.1 mg (75%). 1 H NMR (400MHz, DMSO-d6): δ7.45(d, J=7.5Hz, 3H), 7.41(d, J=7.5Hz, 1H), 7.28(d, J=7.4Hz, 3H), 4.01( s, 1H).

Embodiment 3

[0065] The synthesis of 5-(4-diphenylaminostyrene)-barbituric acid (PB-1) is as follows:

[0066]

[0067] A mixture of 4-(dianilino)-benzaldehyde (0.447g, 3mmol) and barbituric acid (0.384g, 3mmol) in (10ml) ethanol was refluxed for 4 hours. After filtration, the filtrate was concentrated under reduced pressure and further purified by column chromatography (ethyl acetate:petroleum ether=2:1). Yield: (0.75 g) 90%. 1 H NMR (400MHz, CDCl3) δ (ppm): 8.42 (s, 1H), 8.31 (d, J = 8.9Hz, 2H), 7.97 (s, 1H), 7.80 (s, 1H), 7.40 (t, J =7.7Hz,4H),7.24(t,J=6.3Hz,6H),6.94(d,J=8.9Hz,2H).FT-IR(KBr,cm -1 ):3217(N-H), 3061(=C-H), 1672(C=O).

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Abstract

The disclosure provides a barbituric acid derivative and its preparation method and application. The chemical structural formula is wherein R is hydrogen, methyl or phenyl. Its preparation method is: 4-dianilinobenzaldehyde and barbituric acid compound carry out aldol condensation reaction to obtain barbituric acid derivative; The structural formula of described barbituric acid compound is wherein, R is hydrogen, methyl or phenyl. The barbituric acid derivatives provided by the present disclosure have a simple structure and can produce aggregates at high water content, so that they can be used to detect nitroaromatics in aqueous media; they have high sensitivity and good selectivity for detecting nitroaromatics. Advantages such as low detection limit.

Description

technical field [0001] The disclosure belongs to the technical field of fluorescence detection, and relates to a barbituric acid derivative, a preparation method and an application. Background technique [0002] The statements herein merely provide background information related to the present disclosure and may not necessarily constitute prior art. [0003] Aggregation-induced emission (AIE), which is opposite to aggregation-induced quenching (ACQ), was discovered for the first time in 2001, and the main source of the aggregation-induced emission (AIE) effect is the suppression of the occurrence of intermolecular π-π stacking. A common feature of compounds with AEI effect is that they do not emit in pure solution, but emit strong fluorescence in the aggregated state. However, as far as the inventors of the present disclosure know, the synthesis methods of typical compounds with AIE are generally complicated, and most AIE compounds have bulky and complex structures. [000...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/62G01N21/31G01N21/64C09K11/06
CPCC07D239/62C09K11/06C09K2211/1007C09K2211/1014C09K2211/1044G01N21/31G01N21/643G01N2021/6432
Inventor 崔月芝张汉君陶芙蓉郭丽游凯悦
Owner 山东胜利生物工程有限公司
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