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Fluorescent probe for detecting sarin and analogue thereof as well as synthesis method and application of fluorescent probe

A technology of fluorescent probe and synthesis method, which is applied in the field of fluorescent sensing, can solve the problem of inability to detect sarin poison and its simulants, and achieve excellent sensing performance, easy mass preparation, and fast response

Active Publication Date: 2017-05-31
SHANGHAI INST OF MICROSYSTEM & INFORMATION TECH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In order to solve the above-mentioned problem that the sarin poison and its simulant cannot be detected by the existing fluorescence detection method at a lower concentration of the sarin poison and its simulant, the present invention aims to provide a method for sarin poison and its simulant. Fluorescent probe for its mimic detection and its synthesis method and application

Method used

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  • Fluorescent probe for detecting sarin and analogue thereof as well as synthesis method and application of fluorescent probe
  • Fluorescent probe for detecting sarin and analogue thereof as well as synthesis method and application of fluorescent probe
  • Fluorescent probe for detecting sarin and analogue thereof as well as synthesis method and application of fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 Synthesis of sensing material HBP-PFTP and preparation of fluorescent probes

[0037] Synthesis of pyrene-fluorene copolymerized hyperbranched polymer HBP-PFTP with terpyridine as terminal group and preparation of sensing film:

[0038]

[0039] Under nitrogen protection, compound 1 (156mg, 0.3mmol), compound 2 (773mg, 1.2mmol), Pd(PPh 3 ) 4 (76.023mg, 0.06mmol), K 2 CO 3 Aqueous solution (10mL, 2M), dioxane 30mL, heated to reflux for 48 hours. Add compound 3 (200mg) and Pd(PPh 3 ) 4 (50 mg), refluxed for 24 hours and cooled to room temperature. Extract with saturated brine / dichloromethane, combine the organic phases and dry over anhydrous magnesium sulfate, spin off the solvent to obtain a crude product. The resulting crude product was dissolved in a small amount of CH 2 Cl 2 in, dropwise added to CH 3 Precipitate in OH, repeat the steps of dissolution and separation three times, and then reflux for three days with a Soxhlet extractor to wash awa...

Embodiment 2

[0046] Example 2 Synthesis of sensing material TPF and preparation of fluorescent probes

[0047]

[0048] According to the Suzuki-Miyaura method in Example 1, TPF was synthesized and corresponding fluorescent probes were prepared. TFP 1 HNMR and 13 C NMR, elemental analysis results are as follows:

[0049] TPF 1 H NMR spectrum see image 3 . 1 H NMR (500MHz, Chloroform) δ8.82(s, 4H), 8.76, (d, J=4.7Hz, 4H), 8.69(d, J=8.0Hz, 4H), 8.08-8.01(d, J=8.0 Hz, 4H), 7.88(td, J=7.7, 1.8Hz, 4H), 7.83(d, J=8.0Hz, 8H), 7.71-7.64(m, 4H), 7.36(m, 4H), 2.21-2.00 (dd, J=10.8, 5.7Hz, 4H), 1.15(s, 20H), 0.80(t, J=7.0Hz, 10H).TPF 13 C NMR spectrum see Figure 4 . 13 CNMR(126MHz,CDCl3)δ156.34,156.02,151.91,149.79,149.15,142.32,140.39,139.33,137.14,136.85,127.72,127.64,126.12,123.81,121.48,121.40,120.19,118.68,77.26,77.21,77.01, 76.76, 55.42, 40.39, 31.77, 30.02, 29.20, 23.89, 22.59, 14.05. High Resolution MS: search on mass 1005.56; found 1005.5574. Anal. Calcd. for C 71 h 68 N 6 :...

Embodiment 3

[0052] The stability of HBP-PFTP and TPF and the response curves to DCP were tested at their respective maximum excitation wavelength and emission wavelength ( Figure 5 ). As shown in the figure, the stability of HBP-PFTP is better than that of TPF, and the fluorescence intensity remains basically unchanged within 300s. Both HBP-PFTP and TPF respond quickly to DCP saturated steam, and the fluorescence intensity quenching rate reaches 99% within 3s, indicating that both HBP-PFTP and TPF respond well to DCP and are very sensitive. The effect is much better than the results obtained by others, quenching 95% above 10s.

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Abstract

The invention relates to a fluorescent probe for detecting sarin and an analogue thereof. The fluorescent probe comprises a compound which is loaded on a substrate and has a structure shown as a formula I, wherein the formula I is shown in the description. The invention further provides a synthesis method and application of the fluorescent probe for detecting the sarin and the analogue thereof. According to the application provided by the invention, when a compound with the structure shown as the formula I in the fluorescent probe is in contact with the sarin or the DCP (Diethyl Chlorophosphate) in air, the fluorescence intensity and the emission wavelength are both changed, and gas-phase detection of the sarin and the DCP can be realized. The compound with the structure shown as the formula I can have one or more terpyridines; when the sarin or the DCP reacts with one certain pyridine in one certain terpyridine in a molecule, charge transferring from the fluorescent probe to the sarin or the DCP occurs; meanwhile, energy transferring from a polymer core to a peripheral radical occurs, and fluorescent quenching of the whole molecule is caused, so that the fluorescent probe has excellent sensing performance.

Description

technical field [0001] The present invention relates to the technical field of fluorescent sensing, and more specifically relates to a fluorescent probe for detection of sarin poison and its simulant, its synthesis method and application. Background technique [0002] Sarin, whose scientific name is isopropyl meflodronate, is a commonly used military nerve gas. Sarin can inhibit the activity of acetylcholinesterase in organisms, make acetylcholine accumulate in the body, and cause cholinergic nervous system dysfunction. All voluntary and involuntary muscle movements of organisms are a balance between acetylcholine and acetylcholinesterase. After this balance is disrupted, the muscles will only contract but not expand, which will cause paralysis of respiratory function, miosis, gastrointestinal spasm and severe pain, and tear secretion The ducts of blood, sweat and saliva will also discharge a large amount of secretions due to contraction, which makes people die very painful...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/127C07D213/22C09K11/06G01N21/64C08G83/00
CPCC07D213/127C07D213/22C08G83/005C09K11/06C09K2211/1029C09K2211/1466G01N21/6428
Inventor 蒋海波贺庆国付艳艳曹慧敏程建功
Owner SHANGHAI INST OF MICROSYSTEM & INFORMATION TECH CHINESE ACAD OF SCI
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