Tetraphenyl ethylene functionalized oligothiophene derivative as well as preparation method and application thereof

A technology of oligothiophene and tetraphenylethylene, applied in chemical instruments and methods, organic chemistry, fluorescence/phosphorescence, etc., can solve problems such as biological toxicity that is difficult to degrade, environmental pollution, etc.

Active Publication Date: 2020-10-23
NANJING UNIV OF INFORMATION SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These nitroaromatic compounds are not only explosive, but also have problems such as biologica

Method used

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  • Tetraphenyl ethylene functionalized oligothiophene derivative as well as preparation method and application thereof
  • Tetraphenyl ethylene functionalized oligothiophene derivative as well as preparation method and application thereof
  • Tetraphenyl ethylene functionalized oligothiophene derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Weigh 2,5-dibromothiophene (32.8mg, 0.14mmol), tetraphenylethyleneboronic acid (113.2mg, 0.308mmol) and cesium carbonate (110.7mg, 0.315mmol) in a 50mL single-necked flask with an analytical balance. Add reflux condenser, stir bar and dropping funnel. Measure 1.5mL of water and 13.5mL of tetrahydrofuran to dissolve the reactants. Finally the catalyst palladium tetraphosphate (16.4 mg, 0.014 mmol) was added. Seal, pump air, heat up to 70 degrees Celsius, continue to stir, condense and reflux for 48 hours. Then the mixture was extracted, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and evaporated in a rotary evaporator to obtain a crude product. The final product—light yellow solid (35.4 mg, 30%) was obtained by eluting with a silica gel column with a mixed eluent of dichloromethane-petroleum ether. FT-IR (KBrpellets, cm -1 ):3424(w), 3075(b), 2423(m), 2852(w), 1598(w), 1492(w), 1443(w), 1074(w), 762(w), 698(m ). 1 HNMR (400MHz, CDCl 3 ):δ7.35...

Embodiment 2

[0036] Weigh 5,5'-dibromo-2,2'-dithiophene (32.4mg, 0.1mmol), tetraphenylethylene boronic acid (82.8mg, 0.22mmol) and cesium carbonate (81.5mg, 0.25mmol) with an analytical balance 50mL single-necked flask. Add reflux condenser, stir bar and dropping funnel. Measure 1.5mL of water and 13.5mL of tetrahydrofuran to dissolve the reactants. Finally the catalyst palladium tetraphosphate (12 mg, 0.01 mmol) was added. Seal, pump air, heat up to 70 degrees Celsius, continue to stir, condense and reflux for 48 hours. Then the mixture was extracted, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and evaporated in a rotary evaporator to obtain a crude product. The final product—light yellow solid (32.2 mg, 35%) was obtained by elution on a silica gel column with dichloromethane-petroleum ether mixed eluent. FT-IR (KBr pellets, cm -1):3426(m),2956(m),2923(m),2852(m),1493(m),1443(m),1073(w),793(m),790(m),695(m ). 1 H NMR (400MHz, CDCl 3 ): δ7.34(s,2H,thiophene),...

Embodiment 3

[0038] Weigh 5,5"-dibromo-3,3'-dimethyl-2,2':5',2'-thiophene (43.0mg, 0.1mmol), tetraphenylethyleneboronic acid (83mg, 0.22 mmol) and cesium carbonate (81.5mg, 0.25mmol) in a 50mL single-necked flask. Add a reflux condenser, a stir bar and a dropping funnel. Measure 1mL of water and 9mL of tetrahydrofuran to dissolve the reactant. Finally, add catalyst palladium tetraphosphate (12mg, 0.01 mmol). Sealing, pumping, heating up to 70 degrees Celsius, continuous stirring, condensing and reflux for 48h. Then the mixture was extracted, extracted with ethyl acetate, dried with anhydrous sodium sulfate, and rotated in a rotary evaporator to obtain a crude product. Dichloromethane-petroleum ether mixed eluent, silica gel chromatographic column elution, just obtains final product---yellow solid (20.5mg, 20%).FT-IR (KBr pellets, cm -1 ):3437(m),2956(m),2922(m),2851(m),1597(m),1493(m),1465(m),1442(m),1186(m),1080(m ),968(m),752(m),700(m). 1 H NMR (400MHz, CDCl 3 ):δ7.33(s,2H,thiophene),...

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Abstract

The invention discloses a tetraphenyl ethylene functionalized oligothiophene derivative and a preparation method thereof, and provides application of the oligothiophene derivative in detection of nitroaromatic explosives. The oligothiophene derivative prepared by the method is low in cost, good in crystallinity and beneficial to purification, and the structure of the oligothiophene derivative is characterized by 1H NMR. Along with the increase of the concentration of a nitroaromatic compound solution, the fluorescence intensity of the oligothiophene derivative is gradually quenched, and the quenching percentage is as high as 98% or above. The sensing test paper prepared by the method of natural air drying after soaking can quantitatively detect explosives such as nitrobenzene, dinitrobenzene, picric acid and the like. Reliable technical support is provided for rapid, cheap and visual detection of explosives.

Description

technical field [0001] The invention relates to the technical field of oligothiophene compounds, in particular to a tetraphenylethylene functionalized oligothiophene derivative, a preparation method thereof, and an application in rapid detection of nitro explosives. Background technique [0002] Almost all currently used explosives contain electron-deficient nitroaromatics such as 2,4,6-trinitrotoluene, 2,4-dinitrotoluene, 2,4,6-trinitrophenol or picric acid class of compounds. These nitroaromatic compounds are not only explosive, but also have problems such as biological toxicity and refractory degradation, which easily cause serious pollution to the environment. In environmental monitoring, the highly sensitive detection of nitroaromatic compounds in soil and groundwater is also a key problem to be solved urgently. [0003] With the deepening of basic research and application development, fluorescent materials have been widely used in various fields. The research and de...

Claims

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Application Information

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IPC IPC(8): C07D333/08C09K11/06G01N21/64
CPCC07D333/08C09K11/06G01N21/643G01N21/6447C09K2211/1007C09K2211/1092G01N2021/6432Y02E10/549
Inventor 陶涛方东升黄宝磊孙昊李欣烨熊翔晨杨佳瑛
Owner NANJING UNIV OF INFORMATION SCI & TECH
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