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High-selectivity hydrazine ratiometric fluorescent probe and preparation method thereof

A technology of molar ratio and compound, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., to achieve the effect of simple synthesis and good stability

Inactive Publication Date: 2016-03-23
晋江尚京富本环保科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although fluorescent probes for the detection of hydrazine have been reported, most of them are based on the change of fluorescence intensity at a single wavelength to achieve qualitative and quantitative analysis. Such detection methods are easily affected by the distribution of probes and the detection environment. And the influence of factors such as the stability of the instrument

Method used

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  • High-selectivity hydrazine ratiometric fluorescent probe and preparation method thereof
  • High-selectivity hydrazine ratiometric fluorescent probe and preparation method thereof
  • High-selectivity hydrazine ratiometric fluorescent probe and preparation method thereof

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Effect test

Embodiment 1

[0025]

[0026] (Scheme 1) 4-hydroxy-1,8-naphthalimide (269mg, 1.0mmol), 4-bromobutyric acid (166mg, 1.0mmol), 4-dimethylaminopyridine (122mg, 1.0mmol) and di Cyclohexylcarbodiimide (412mg, 2.0mmol) was dissolved in 20mL of dry dichloromethane, reacted at room temperature for 6h, evaporated under reduced pressure to obtain a crude product, and then separated by column chromatography using dichloromethane to obtain 179mg of a light yellow pure product , and the yield was 43%.

[0027] (Scheme 2) 4-hydroxy-1,8-naphthalimide (269mg, 1.0mmol), 4-bromobutyric acid (332mg, 2.0mmol), 4-dimethylaminopyridine (244mg, 2.0mmol) and di Cyclohexylcarbodiimide (618 mg, 3.0 mmol) was dissolved in 20 mL of dry dichloromethane, reacted at room temperature for 6 hours, evaporated under reduced pressure to obtain a crude product, and then separated by column chromatography using dichloromethane to obtain 283 mg of a light yellow pure product , and the yield was 68%.

[0028] (Scheme 3) 4-hy...

Embodiment 2

[0032] The inventor of the present invention has carried out following test: (a) the impact of different concentrations of hydrazine (0~100 μ M) on the probe (5 μ M) fluorescence spectrum; Insert figure is the ratio of fluorescence intensity at 547nm place and fluorescence intensity at 452nm place and added hydrazine The linear relationship between concentrations. The above determinations were made in a system containing ethanol and water (3:7, V / V) containing 5mM phosphate buffered saline (PBS), pH 7.4, and all spectral tests were measured at 25°C after adding hydrazine for 15 minutes of. See results figure 1 .

[0033] from figure 1 It can be seen that with the increase of the concentration of hydrazine in the probe solution, the fluorescence emission peak at 452nm decreases gradually, and at the same time, a new emission peak at 547nm occurs and gradually increases. The ratio of the intensity to the fluorescence intensity at 452nm has a good linear relationship. Theref...

Embodiment 3

[0035] Effect of different analytes (50 μM) on the fluorescence spectra of probes (5 μM). Analytes include: ethylenediamine EDA, dimethylamine DMA, triethylamine TEA, n-butylamine nBA, ammonium acetate AA, sulfide ion S 2- , Chloride ion Cl - , bromide ion Br - , iodide ion I - , Sulfate ion SO 4 2- , Thiocyanate ion SCN- , glutathione GSH and hydrazine, and their concentrations are all 50 μM. All test conditions are completed in ethanol and water (3:7, V / V) containing 5mM phosphate buffered saline (PBS), pH 7.4 system, and all spectra are at 25°C after the addition of analyte for 15min test the result. Pipette 25μL of the probe stock solution (1mM) into a 5mL colorimetric tube, then add 1.5mL ethanol, 250μL of 100mMPBS, and then pipette 25μL of the above analyte stock solution (10mM) into the colorimetric tube, and then set it with ultrapure water. Make up to 5mL. Shake well, let it stand for 15min, then measure. The result is as figure 2 shown.

[0036] from fi...

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Abstract

The invention relates to high-selectivity hydrazine ratiometric fluorescent probes and preparation methods thereof. The probes are not only high in selectivity in hydrazine recognition but also flexible in hydrazine qualitative and qualitative analysis carried out according to a fluorescence method. The probes are capable of quickly responding to hydrazine to realize real-time hydrazine detection and are available for long-term storage and use due to property stability. In addition, the probes are capable of realizing accurate qualitative analysis on hydrazine according to a ratiometric fluorescence method and have excellent anti-interference performances. Synthesis conditions of the probes are mild relatively, and the probes can be synthesized simply only by one-step reaction.

Description

technical field [0001] The invention relates to a preparation method of 4-bromobutyric acid naphthalimide compound as a hydrazine ratio fluorescent probe and an application for highly selective recognition of hydrazine. Background technique [0002] Hydrazine (NH 2 NH 2 ), as an important industrial chemical, is widely used in many fields, such as medicine, emulsifier, dyestuff and textile, catalyst, corrosion inhibitor and pesticide involved in military, aerospace, industry and agriculture. Hydrazine is flammable and explosive, and is best known as a high-energy fuel in rocket propulsion systems. Hydrazine has a strong reducing ability and is also used in the corrosion protection of metals. In the field of extraction, hydrazine is also used as a plant growth regulator. In the pharmaceutical field, hydrazine is used as an antibacterial drug. However, hydrazine is also toxic. With the wide application of hydrazine in various fields, it is easy to cause environmental poll...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/14C09K11/06G01N21/64
CPCC07D221/14C09K11/06C09K2211/1029G01N21/643
Inventor 叶龙武张艳
Owner 晋江尚京富本环保科技有限公司
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