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Fluorescent probe for detecting mustard gas, detection test paper and preparation method thereof

A fluorescent probe and mustard gas technology, which is applied in the directions of fluorescence/phosphorescence, luminescent materials, measuring devices, etc., can solve the problems of complex operation steps, difficult probe synthesis, non-specificity, etc., and achieves simple synthesis method, sensitive detection of mustard gas, reaction mild effects

Active Publication Date: 2020-11-06
UNIV OF SCI & TECH OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The published literature on gas phase detection of mustard gas includes British "Chemical Communications" (Chem. Selective and Sensitive "Turn-On" Fluorescence Chemosimeter for the Detection of Mustard Gas.) and British "RSC Progress" (RSC Adv., 2015, 5, 91946, V.Kumar, H.Rana, Selective and Sensitive Chromogenic and Fluorogenic Detection of Sulfur Mustard in Organic, Aqueous and Gaseous Maedium.) reported the gas-phase detection of simple mustard gas that adopts thin layer chromatography (TLC plate) to adsorb fluorescent probes to carry out, but there are still many shortcomings, such as: probe synthesis is difficult or the operation steps are complicated, and Non-specific, prone to false positives, etc., these problems limit their application

Method used

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  • Fluorescent probe for detecting mustard gas, detection test paper and preparation method thereof
  • Fluorescent probe for detecting mustard gas, detection test paper and preparation method thereof
  • Fluorescent probe for detecting mustard gas, detection test paper and preparation method thereof

Examples

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Embodiment 1

[0023] Embodiment 1: the synthesis of probe compound Pr-Cou-SH

[0024]

[0025] Under nitrogen protection at 0°C, the chlorine-substituted coumarin compound 9-chloro-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2 , 1-ij] quinoline (200mg, 0.69mmol) was added to absolute ethanol (10mL), sodium hydrosulfide (470mg, 8.28mmol) was slowly added dropwise to the above solution, and monitored by thin layer chromatography until no chlorine substitution After the coumarin compound 9-chloro-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline residue , the solvent was removed under reduced pressure, and the crude reaction product was purified and isolated by column chromatography to obtain a dark yellow solid product (84 mg), with a yield of 42%.

[0026] Its H NMR spectrum is: 1 HNMR (400MHz, CDCl 3 ,25°C, TMS) δ=6.99(s,1H,Ar-H),5.99(s,1H,Ar-H),3.64(s,1H,SH),3.27(m,4H,CH 2 ×2), 2.87(t, J=6.4Hz, 2H, CH 2 ), 2.78(t, J=6.0Hz, 2H, CH 2 ),1.97(m,4H,CH 2 ×2)ppm...

Embodiment 2

[0030] Embodiment 2: the synthesis of probe compound Pr-Cou-SH

[0031] Under nitrogen protection at 0°C, the chlorine-substituted coumarin compound 9-chloro-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2 , 1-ij] quinoline (200mg, 0.69mmol) was added to absolute ethanol (10mL), sodium hydrosulfide (630mg, 11.04mmol) was slowly added dropwise to the above solution, and no chlorine substitution was monitored by thin layer chromatography. After the coumarin compound 9-chloro-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline residue , the solvent was removed under reduced pressure, and the crude reaction product was purified and isolated by column chromatography to obtain a yellow solid product (90 mg), with a yield of 45%.

[0032] The yellow solid product prepared in this example proves that the product is the probe compound 9-mercapto-2,3,6,7-tetrahydro-1H according to its proton nuclear magnetic resonance spectrum, carbon nuclear magnetic resonance spe...

Embodiment 3

[0033] Embodiment 3: the synthesis of probe compound Pr-Cou-SH

[0034] Under nitrogen protection at 0°C, the chlorine-substituted coumarin compound 9-chloro-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2 , 1-ij] quinoline (200mg, 0.69mmol) was added to absolute ethanol (10mL), sodium hydrosulfide (830mg, 14.50mmol) was slowly added dropwise to the above solution, and monitored by thin-layer chromatography until no chlorine substitution After the coumarin compound 9-chloro-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline residue , the solvent was removed under reduced pressure, and the crude reaction product was purified and isolated by column chromatography to obtain an orange solid product (82 mg), with a yield of 41%.

[0035] The orange-yellow solid product prepared in this example proves that the product is the probe compound 9-mercapto-2,3,6,7-tetrahydro- 1H, 5H, 11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline (Pr-Cou-SH).

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Abstract

The invention discloses a fluorescent probe for detecting mustard gas, detection test paper and a preparation method thereof. The fluorescent probe is characterized in that N,N-dicyclopropyleneamino substituted coumarin is used as a fluorescent chromophore, and phenol sulfydryl is used as a reaction site of mustard gas; a chlorine-substituted coumarin compound and sodium hydrosulfide are added into an ethanol solution, stirring is performed at 0-10 DEG C until chlorine-substituted coumarin is completely reacted, a solvent is removed under reduced pressure, and column chromatography purification is performed to obtain a probe compound 9-sulfydryl-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline; and the probe compound 9-sulfydryl-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline, trioctylamine and polyoxyethylene are dissolved in ethanol to prepare a solution, filter paper is infiltrated with the solution, airing is performed, and the paper is cut into strips to obtain the mustard gas detection test paper. According to the invention, the probe compound disclosed by the invention is simple to synthesize, high in detection sensitivity, low in detection limit and high in selectivity, and the prepared test paper can be used for quickly and visually monitoring mustard gas in a gas phase, is low in cost and good in portability, and has a very goodapplication prospect.

Description

technical field [0001] The invention belongs to the technical field of mustard gas analysis and detection, and in particular relates to a synthesis method of a fluorescent probe compound for highly sensitive detection of mustard gas based on a coumarin dye, and a preparation method of a mustard gas detection test paper. Background technique [0002] Mustard gas, also known as 2,2'-dichloroethyl sulfide (SM), pure mustard gas is a colorless oily liquid with a slightly sweet smell, industrial mustard gas is mostly yellow or dark brown, with a pungent mustard smell . During the First World War, mustard gas was used as a chemical poison, causing a large number of casualties, and it was called the "King of Poison Gas". Mustard gas is insoluble in water but easily soluble in fat. It can invade the human body through the skin and respiratory tract, causing redness, swelling, ulceration and necrosis of the skin. In addition, in a polar system, mustard gas forms a three-membered ri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/147C09K11/06G01N21/64G01N21/78
CPCC07D491/147C09K11/06G01N21/6428G01N21/78C09K2211/1048G01N2021/6443
Inventor 宋钦华薛敏杰刘石磊冯伟邢中方张巧利
Owner UNIV OF SCI & TECH OF CHINA