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Barbituric acid derivative as well as preparation method and application thereof

Active Publication Date: 2019-07-19
QILU UNIV OF TECH
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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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  • Barbituric acid derivative as well as preparation method and application thereof
  • Barbituric acid derivative as well as preparation method and application thereof
  • Barbituric acid derivative as well as preparation method and application thereof

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 invention provides a barbituric acid derivative as well as a preparation method and application thereof. The chemical structural formula is shown in the specification, and R is hydrogen, methyl orphenyl. The preparation method comprises the following steps: carrying out an aldol condensation reaction on 4-diphenylamino benzaldehyde and a barbituric acid compound to obtain a barbituric acid derivative, wherein the structural formula of the barbituric acid compound is shown in the specification, and R is hydrogen, methyl or phenyl. The barbituric acid derivative provided by the invention issimple in structure, and can generate aggregates under a high water content, so that the barbituric acid derivative can be used for detecting nitroaromatics in an aqueous medium; and the barbituric acid derivative has the advantages of high sensitivity, good selectivity, low detection limit and the like for detecting nitroaromatics.

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 Applications(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 QILU UNIV OF TECH
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