Organic fluorescent molecule and preparation method thereof, fluorescent sensor and application thereof, and standard fluorescent card

A fluorescent sensor and fluorescent molecule technology, applied in the field of fluorescent sensing, can solve the problems of lack of repeatability, long response time, complex material synthesis, etc., and achieve the effects of improving sensitivity and response speed, efficient charge transfer, and enhanced fluorescence capability.

Active Publication Date: 2020-12-11
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still some problems, such as: (1) most of the reported fluorescent sensing materials have a long response time, and some are still on the order of minutes; (2) lack of repeatability, which limits its further practical application; (3) ) Compared with the fluorescence color and color change effect, the fluorescence enhancement and fluorescence quenching responses are more easily affected by the external environment, which affects the accuracy of the test results; (4) The material synthesis is complex and the application cost is high

Method used

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  • Organic fluorescent molecule and preparation method thereof, fluorescent sensor and application thereof, and standard fluorescent card
  • Organic fluorescent molecule and preparation method thereof, fluorescent sensor and application thereof, and standard fluorescent card
  • Organic fluorescent molecule and preparation method thereof, fluorescent sensor and application thereof, and standard fluorescent card

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preparation example Construction

[0054] The present invention provides a method for preparing organic fluorescent molecules described in the above technical solution, comprising the following steps:

[0055] Mixing a compound containing group A, a terpyridine compound, a catalyst, a solvent and an alkaline reagent, and performing a coupling reaction to obtain an organic fluorescent molecule having a structure shown in formula I;

[0056] The compound containing group A is naphthalene, anthracene, naphthacene, carbazole, phenothiazine, phenoxazine, phenazine, dimethylacridine, diphenylamine, triphenylamine, tetraphenylethylene, pyrene, quinone Oxaline or aniline;

[0057] The terpyridine compound has a structure shown in formula II:

[0058] Wherein, X is Cl, Br or I.

[0059] In the present invention, unless otherwise specified, the required preparation materials are commercially available products well known to those skilled in the art.

[0060] In the present invention, the compound containing group A ...

Embodiment 1

[0093] The preparation process of the organic fluorescent molecule T1 is as follows:

[0094]

[0095] Specific steps include:

[0096] Under the protection of argon, carbazole (1.67g, 0.01mmol), 4'-(4-bromophenyl)-2,2':6',2"-terpyridine (3.88 g, 0.01mol) and cesium carbonate (4.88g, 0.015mmol), stirred at room temperature, added 40mLN, N-dimethylformamide, under the condition of protective gas, the resulting mixture was frozen-vacuumized once, the The frozen reagent is liquid nitrogen, the freezing temperature is -80°C, and the time is 5 minutes. Vacuumize the system until the system pressure drops below 500 mTorr, and then add the main catalyst CuI (95mg, 0.5mmol) and the cocatalyst 1,10-ortho Phenanthroline (45 mg, 0.23 mmol), repeat the freezing-vacuum operation three times, heat to 160 ° C, carry out the coupling reaction for 8 h, cool to room temperature, and dichloromethane and water (volume ratio of dichloromethane and water: 3:1) extraction, after washing with wa...

Embodiment 2

[0100] The preparation process of the organic fluorescent molecule T2 is as follows:

[0101]

[0102] Specific steps include:

[0103] Under the protection of argon, add phenothiazine (2g, 0.01mmol), 4'-(4-bromophenyl)-2,2':6',2"-terpyridine (3.88 g, 0.01mol) and cesium carbonate (4.88g, 0.015mmol), stirred at room temperature, added 40mLN, N-dimethylformamide, under the condition of protective gas, the resulting mixture was frozen-vacuumized once, the The frozen reagent is liquid nitrogen, the freezing temperature is -80°C, and the time is 5 minutes. Vacuumize the system until the system pressure drops below 500 mTorr, and then add the main catalyst CuI (95mg, 0.5mmol) and the cocatalyst 1,10-ortho Phenanthroline (45 mg, 0.23 mmol), repeat the freezing-vacuum operation three times, heat to 160 ° C, carry out the coupling reaction for 8 h, cool to room temperature, and dichloromethane and water (volume ratio of dichloromethane and water: 3:1) extraction, after washing wi...

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Abstract

The invention provides an organic fluorescent molecule and a preparation method thereof, a fluorescent sensor and application thereof, and a standard fluorescent card, and belongs to the technical field of fluorescent sensing. A skeleton of the organic fluorescent molecule provided by the invention is composed of 2,2':6',2''-terpyridyl (TPY) and an electron donating group, the TPY group is used asan electron acceptor group, and after the electron donating group (i.e., a group A in a formula I) is introduced, an intramolecular charge transfer state (CT) can be formed to construct a donor-acceptor type organic fluorescent material; and meanwhile, the TPY group can also be used as a recognition site of sensing reaction to detect electrophilic nerve poison molecules. After the organic fluorescent molecule is used to prepare the sensor, efficient and rapid fluorescence / chromogenic dual-channel detection of liquid-phase and gas-phase trace sarin poisoning agents (Sarin) and / or diethyl chlorophosphate (DCP) can be realized, and the organic fluorescent molecule is high in response speed, good in selectivity, high in sensitivity and reusable.

Description

technical field [0001] The invention relates to the technical field of fluorescent sensing, in particular to an organic fluorescent molecule and a preparation method thereof, a fluorescent sensor and its application, and a standard fluorescent card. Background technique [0002] Nerve agents include G-type nerve agents (sarin, soman, and tabun) and V-type nerve agents (such as VX), which are a class of highly toxic organophosphate compounds that irreversibly inhibit neurons in organisms. The activity of acetylcholine ester in the synapse causes the excessive accumulation of acetylcholinesterase in the body, causing the muscle to only contract but not expand, thus causing serious neurological disorders. Because of its strong toxicity, quick action, stable properties and easy production, it is often used to prepare deadly chemical warfare agents. Sarin, whose scientific name is isopropyl meflodronate, is a highly toxic and volatile liquid. Sarin poisonous gas will cause grea...

Claims

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Application Information

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IPC IPC(8): C07D401/14C07D417/14C09K11/06G01N21/64
CPCC07D401/14C07D417/14C09K11/06C09K2211/1029C09K2211/1037G01N21/6428G01N2021/6432
Inventor 张明李峰郑平
Owner JILIN UNIV
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