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Fluorescence probe for visually detecting hydrazine based on benzothiazole as well as preparation method and use of fluorescence probe

A technology of benzothiazole and fluorescent probe, which is applied in the fields of biological analysis and environmental analysis, can solve the problems of poor anti-interference ability, influence on hydrazine detection, and low sensitivity, and achieve strong anti-interference ability, simple and fast detection process, and fast response fast effect

Inactive Publication Date: 2018-04-06
HUBEI POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some fluorescent probes for the detection of hydrazine have been reported, their detection of hydrazine in complex environments is affected due to their low sensitivity, poor anti-interference ability, and slow response.

Method used

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  • Fluorescence probe for visually detecting hydrazine based on benzothiazole as well as preparation method and use of fluorescence probe
  • Fluorescence probe for visually detecting hydrazine based on benzothiazole as well as preparation method and use of fluorescence probe
  • Fluorescence probe for visually detecting hydrazine based on benzothiazole as well as preparation method and use of fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] The synthesis of embodiment 1 probe ZY9

[0023] The synthetic route of probe ZY9 is as follows:

[0024]

[0025] Add 1g (0.0068mol) of phthalic anhydride and 1.42g (0.0068mol) of 2-(4-aminophenyl)benzothiazole into a 100mL round bottom flask, then add 50mL of glacial acetic acid, heat to 120°C, and stir Reflux for 12 hours, judge the reaction progress by thin-layer chromatography, until the raw materials are consumed. After the reaction was completed, it was quickly placed in ice water to cool, a large amount of gray-green solid precipitated out, left to stand, and filtered under reduced pressure, the crude product was rinsed with 20 mL of ice water for 2-3 times, and dried to obtain gray-green solid ZY9. m.p.312-314℃; ESI-MS: m / z356 (M + ); 1 H NMR (300MHz, CDCl 3 ,ppm): δ7.32(d,2H,J 4.5Hz),7.33–7.67(m,4H),7.83–8.00(m,4H),8.25(d,2H,J 8.4Hz).

Embodiment 2

[0026] The selectivity research of embodiment 2 probe ZY9 to different detection species

[0027] The probe ZY9 prepared in Example 1 was dissolved in DMF to prepare a probe mother solution with a concentration of 1mmol / L; distilled water was used as a solvent to prepare various concentrations of the same 1mmol / L detection species (K + , Ca 2+ , Na + ,Mg 2+ ,Zn 2+ , Fe 3+ , Fe 2+ , Ni 2+ ,Co 2+ ,Mn 2+ ,Cu 2+ ,F - , Cl - ,Br - , I - ,S 2- , SO 4 2- ,SCN - ,CO 3 2- , SO 3 2- ,NO 3 - , Ac - ,NO 2 - ,NH 3 ·H 2 O,H 2 o 2 ,N 2 h 4 ,NH 2 CONH 2 ) stock solution. Use a pipette gun to add the probe and detection species with a ratio of 1:3, and then dilute with DMF and double distilled water (V DMF :V H2O =1:9), so that the final concentrations of the probe and detection species in the fluorescence cuvette were 10 μmol / L and 30 μmol / L, respectively. Shake the prepared solutions evenly, react for 30min, and then test their fluorescence spectra. Depe...

Embodiment 3

[0028] Example 3 Interference research of different detection species on the recognition of hydrazine by probe ZY9

[0029] In the probe ZY9 solution (1mmol / L) that embodiment 1 prepares, add the hydrazine solution (1mmol / L) of 3 times of volumes, then add the 1mmol / L various competing species of 10 times of volumes (K + , Ca 2+ , Na + ,Mg 2+ ,Zn 2+ , Fe 3+ , Fe 2+ , Ni 2+ ,Co 2+ ,Mn 2+ ,Cu 2+ ,F - , Cl - ,Br - , I - ,S 2- , SO 4 2- ,SCN - ,CO 3 2- , SO 3 2- ,NO 3 - , Ac - ,NO 2 - ,NH 3 ·H 2 O,H 2 o 2 ,NH 2 CONH 2 ) and then diluted with DMF and double distilled water (V DMF :V H2O =1:9), so that the final concentrations of the probe, hydrazine solution and competing species in the fluorescence cuvette were 10 μmol / L, 30 μmol / L, and 100 μmol / L, respectively. After the solution was mixed evenly, it was shaken for another 30 minutes to test the fluorescence intensity. Such as figure 2 As shown, compared with the blank test solution (no compet...

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Abstract

The invention provides a fluorescence probe ZY9 for visually detecting hydrazine based on benzothiazole as well as a preparation method and use of the fluorescence probe ZY9. The fluorescence probe ZY9 can be prepared through the reaction of 2-(4-aminophenyl)benzothiazole and phthalic anhydride in a certain proportion and is easy to synthesize and purify, relatively high in yield and low in cost;the hydrazine fluorescence probe is a fluorescence enhanced fluorescence probe, has relatively selectivity and sensitivity to hydrazine, is strong in anti-jamming capability and high in response speedand can be used for visually detecting hydrazine through the significant change of the fluorescence color; the probe is good in stability and can be stored for a long time for use; besides, the probeis suitable for detecting the content of hydrazine and realizing the fluorescence imaging of hydrazine in a living cell level, and hydrazine in a water solution with a certain concentration can be detected by virtue of probe test paper. A hydrazine detection method provided by the invention has the advantages of easiness and convenience in operation, easiness in popularization and the like and has wide application prospects in the fields of environment and biological science.

Description

【Technical field】 [0001] The invention relates to the fields of environmental analysis and biological analysis and detection, in particular to a benzothiazole-based fluorescent probe for visually detecting hydrazine, a preparation method and application thereof. 【Background technique】 [0002] Hydrazine (N 2 h 4 ), also known as hydrazine, is a chemical raw material with strong reducibility. It is widely used in industrial production and can be used to produce preservatives, antioxidants, herbicides and plant growth regulators. In addition, N 2 h 4 It has a high heat of combustion and can be used as fuel for rockets and fuel cells. However N 2 h 4 It is a toxic substance, and its leakage during production and transportation will cause environmental pollution. There is no endogenous hydrazine in living cells, but hydrazine can be absorbed by the human body through inhalation or skin contact, causing serious damage to the liver, lungs, kidneys and central nervous system...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/10C09K11/06G01N21/64
CPCC07D417/10C09K11/06C09K2211/1037G01N21/6428G01N21/6486
Inventor 张勇刘桂琴龚旭艳
Owner HUBEI POLYTECHNIC UNIV
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