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Fluorescence sensing material, preparation method thereof and application in high-sensitivity distinguished detection of chemical warfare agents

A technology of fluorescent materials and chemical warfare agents, applied in the field of organic fluorescent sensing materials

Active Publication Date: 2019-12-20
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the research on the high-sensitivity differential detection of nerve agents and erosive toxins. Therefore, the development of high-sensitivity sensors for the differential detection of chemical warfare agents has important scientific significance and practical value.

Method used

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  • Fluorescence sensing material, preparation method thereof and application in high-sensitivity distinguished detection of chemical warfare agents
  • Fluorescence sensing material, preparation method thereof and application in high-sensitivity distinguished detection of chemical warfare agents
  • Fluorescence sensing material, preparation method thereof and application in high-sensitivity distinguished detection of chemical warfare agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0137] Prepare molecule A with the formula 1 .

[0138]

[0139] (1) Add 3.0 grams of 4-bromophenol, 1.5 grams of (S)-2-butanol, 5.4 grams of triphenylphosphine and 40 milliliters of tetrahydrofuran into a 100ml round-bottomed flask. Slowly add 4.2 g of diisopropyl azodicarboxylate, rise to room temperature, stir for 5 hours, and separate by column chromatography to obtain 1-bromo-4-((R)-sec-butoxy)benzene;

[0140] (2) Add 3.0 grams of the product obtained in step (1) to a 100ml round bottom flask, add 4.0 grams of pinacol ester boronate, 3.8 grams of potassium acetate and 0.5 grams of 1,1'-bis(diphenylphosphine base) ferrocene palladium dichloride (II), 30 milliliters of 1,4-dioxane, reacted overnight at 80°C under Ar protection, and obtained 2-(4-((R)-sec-butyl Oxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;

[0141] (3) Add 1.5 grams of the product obtained in step (2) to a 100ml round bottom flask, 1.9 grams of 4,7-dibromobenzothiadiazole, 0.3 gram of tetraphen...

Embodiment 2

[0154] Prepare molecule B with the formula 1 .

[0155]

[0156] (1) Add 0.86 gram of 4-(4-pyridyl) phenylboronic acid, 1.5 gram of 4,7-dibromobenzothiadiazole, 0.25 gram of tetraphenylphosphine palladium, 1.78 gram of potassium carbonate in a 100ml round bottom flask , 30 milliliters of 1,4-dioxane and 6 milliliters of water were reacted overnight at 80°C under the protection of Ar, and 4-bromo-7-(4-(4-pyridyl)phenyl)benzo was obtained after separation by column chromatography Thiadiazole;

[0157] (2) Add 1.2 grams of the product obtained in step (1) to a 100ml round bottom flask, add 0.99 grams of pinacol ester boronate, 0.96 grams of potassium acetate and 0.12 grams of 1,1'-bis(diphenylphosphine Base) ferrocene palladium dichloride (II), 30 milliliters 1,4-dioxane, 80 ℃ overnight reaction under Ar protection, obtain 2-(4-(4-pyridyl) benzene after column chromatography separation base)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;

[0158] (3) 1.3 grams of products obtain...

Embodiment 3

[0169] By the molecular structure A prepared by embodiment 1 1 A film composed of self-assembled nanoparticles was used for the fluorescence detection of mustard gas and sarin.

[0170] will be given by molecular structure A 1 The self-assembled nanoparticle aggregates are coated in self-made quartz tubes, and then loaded into the detection equipment independently developed by the laboratory. The microsphere aggregates are excited by a 385 nm excitation light source, and the light intensity at 520-560 nm is integrated. , plotting light intensity versus time. The vapors of mustard gas or sarin of different concentrations were sucked with a 10 ml syringe, and blown into the quartz tube at a speed of 1 ml / s. The test results showed that the blowing of mustard gas of different concentrations all led to fluorescence quenching (such as Figure 11 shown), sarin insufflation does not cause fluorescence quenching (eg Figure 12 shown). Based on this, we propose material A1 The mech...

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Abstract

The invention provides a fluorescent material containing one compound represented by a formula (III) shown in the specification. When the fluorescent material is in contact with chemical warfare agents such as mustard gas and sarin, the fluorescence can have an enhancement or quenching phenomenon, the concentration for detecting the chemical warfare agent vapor is in the range from a ppb level toa ppm level, and the fluorescent material has no obvious response to common interference gas such as organic solvents (thousands ppm to tens of thousands ppm). The fluorescent material provided by theinvention has strong stability, a high fluorescence quantum yield and wide application prospects; and a method for detecting the chemical warfare agents provided by the invention realizes the distinguished detection of a blister agent and a neurotoxic agent, and has very high practicability.

Description

technical field [0001] The invention belongs to the field of organic fluorescent sensing materials, in particular to a fluorescent sensing material and a preparation method thereof and its application in high-sensitivity discrimination and detection of chemical warfare agents. Background technique [0002] Nerve agents and corrosive agents are two important chemical warfare agents. Nerve agents mainly inhibit acetylcholinease in nerve synapses, causing acetylcholine to accumulate in the body in large quantities, thereby causing nervous system disorders. Clinical manifestations include convulsions and dyspnea. Nerve agents are organophosphorus or organophosphate compounds, mainly divided into G-type nerve agents (sarin, soman, tabun) and V-type nerve agents (Viex). Erosive agents spontaneously form a highly reactive and unstable intermediate through intramolecular cyclization, which is easy to combine with a variety of biomolecules with electro-rich groups (such as sulfhydr...

Claims

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Application Information

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IPC IPC(8): C07D285/14C07D417/14C09K11/06G01N21/64
CPCC07D285/14C07D417/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1051G01N21/643G01N2021/6432
Inventor 车延科崔林丰程传钦邱长坤
Owner INST OF CHEM CHINESE ACAD OF SCI
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