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Piperazine-modified tetraphenylethylene derivative and application thereof

A technology of tetraphenylethylene and triphenylethylene, which is applied in the field of organic photoelectric functional materials, can solve problems such as red blood cell destruction and human poisoning, and achieve the effects of rapid response, short response time, and simple preparation method

Active Publication Date: 2018-10-09
杭州芬得检测技术有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Moreover, the intake of TNP can cause human poisoning. In mild cases, there will be symptoms such as headache, nausea, vomiting, abdominal pain, and in severe cases, it will cause damage to its red blood cells.
However, all nitro explosives show strong electron affinity, and it is difficult to specifically detect TNP from other nitro compounds. Therefore, it is of great significance to develop efficient and specific methods for detecting TNP

Method used

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  • Piperazine-modified tetraphenylethylene derivative and application thereof
  • Piperazine-modified tetraphenylethylene derivative and application thereof
  • Piperazine-modified tetraphenylethylene derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 Synthesis of 1-(4'-Boc-1-piperazinylphenyl)-1,2,2-triphenylethylene

[0046] Under the protection of high-purity nitrogen, 411mg of 1-(4'-bromophenyl)-1,2,2-triphenylethylene, 485mg of 4-(4'-Boc-1-piperazinyl)phenylboronic acid Nacohol ester and 160mg of sodium carbonate (molar ratio 1:1.2:1.5) are mixed and dissolved in a mixed solvent prepared by 80mL of tetrahydrofuran and 20mL of water (volume ratio is 4:1), and after completely dissolving, add 6.2mg of Tetrakistriphenylphosphine palladium catalyst, the consumption of tetrakistriphenylphosphine palladium catalyst is 1.5wt% of 1-(4'-bromophenyl)-1,2,2-triphenylethylene, reflux under 90 ℃ oil bath . After 12 hours of reaction, the oil bath was removed, and the system was naturally cooled to room temperature. Part of the organic solvent was removed with a rotary evaporator, and the mixture was concentrated to 1 / 3 of its original volume. Then extract the system with dichloromethane and saturated brine 60mL ...

Embodiment 2

[0047] Example 2 Synthesis of 1-(4'-Boc-1-piperazinylphenyl)-1,2,2-triphenylethylene

[0048] Under the protection of ordinary nitrogen, 411mg of 1-(4'-bromophenyl)-1,2,2-triphenylethylene, 606mg of 4-(4'-Boc-1-piperazinyl)phenylboronic acid pinaca Alcohol ester and 202mg of potassium carbonate (molar ratio 1:1.5:1.5) are mixed and dissolved in a mixed solvent prepared by 100mL of acetonitrile and 20mL of water (volume ratio is 5:1). Triphenylphosphine palladium catalyst, the amount of four triphenylphosphine palladium catalyst is 2.0wt% of 1-(4'-bromophenyl)-1,2,2-triphenylethylene, reflux under 100°C oil bath heating . After 10 hours of reaction, the oil bath was removed, and the system was naturally cooled to room temperature. Part of the organic solvent was removed with a rotary evaporator, and the mixture was concentrated to 1 / 3 of its original volume. Then the system was extracted with dichloromethane with a volume ratio of 1:2 and 60 mL of saturated saline for a tota...

Embodiment 3

[0049] Example 3 Synthesis of 1-(4'-Boc-1-piperazinylphenyl)-1,2,2-triphenylethylene

[0050] Under argon protection, 410 mg of 1-(4'-bromophenyl)-1,2,2-triphenylethylene, 485 mg of 4-(4'-Boc-1-piperazinyl) phenylboronic acid pinaca Alcohol ester and 160mg of sodium carbonate (molar ratio 1:1.2:1.5) are mixed and dissolved in a mixed solvent prepared by 80mL of tetrahydrofuran and 20mL of water (volume ratio is 4:1), and after completely dissolving, add 6.2mg of tetrahydrofuran Triphenylphosphine palladium catalyst, tetrakistriphenylphosphine palladium catalyst used in an amount of 1.5wt% of 1-(4'-bromophenyl)-1,2,2-triphenylethylene, refluxed in an oil bath at 90°C. After reacting for 18 hours, the oil bath was removed, and the system was naturally cooled to room temperature. Part of the organic solvent was removed with a rotary evaporator, and the mixture was concentrated to 1 / 3 of its original volume. Then extract the system with 60mL of dichloromethane and saturated sali...

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Abstract

The invention discloses a piperazine-modified tetraphenylethylene derivative which has a structural formula as shown in formula I, and discloses a preparation method of the piperazine-modified tetraphenylethylene derivative. The preparation method comprises the following steps: coupling 1-(4'-bromophenyl)-1, 2, 2-triphenylethylene with 4-(4'-carbonate-1-piperazinyl) phenylboronic acid pinacol ester by a Suzuki reaction; and then performing concentration, extraction, drying, column chromatography and other separation and purification treatments to finally obtain the piperazine-modified tetraphenylethylene derivative. The invention further provides application of the piperazine-modified tetraphenylethylene derivative as a fluorescence detection medium for detecting aromatic nitro-explosive TNP in a dispersion system for a mixed solvent of organic solvent / water; and a minimum detection limit of the TNP can reach a level of 1*10<-6> M.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, in particular to a piperazine-modified tetraphenylethylene derivative and its application, especially in the detection of aromatic nitro explosives 2,4,6-trinitrophenol (TNP) in the application. Background technique [0002] Nitroaromatics include nitrobenzene (NB), 4-nitrotoluene (4-NT), 2,4,6-trinitrophenol (TNP), 2,4,6-trinitrotoluene (TNT), etc. Is a common component of explosives, they have strong explosive power and low safety factor. At present, nitro compounds have received great attention in terms of national security and environmental pollution, so the detection of nitro compounds is particularly important. [0003] Currently developed detection techniques for aromatic nitro explosives include mass spectrometry, ion mobility spectrometry, electrochemical methods, and colorimetry, but these conventional detection and analysis methods have disadvantage...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/205C09K11/06G01N21/64
CPCC07D295/205C09K11/06C09K2211/1007C09K2211/1044G01N21/643G01N2021/6432
Inventor 马辉傅得锋陈德良姚伟宣孙剑聪宣宇
Owner 杭州芬得检测技术有限公司
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