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Ratiometric fluorescent probe for detecting hydrazine, and preparation method thereof

A fluorescent probe and ratiometric technology, applied in the field of fluorescent probes, can solve problems such as interference signal output and rare probes, and achieve the effects of good selectivity, strong anti-interference ability, and high sensitivity

Active Publication Date: 2014-10-22
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although there are reports on fluorescent sensing probes for hydrazine, there are still few probes that can achieve ratiometric fluorescence measurement.
For fluorescence detection, when the single fluorescence intensity is used as the only detection signal, there are many unstable factors, such as instrument efficiency, detection environment, probe concentration, etc., which may interfere with the output of the signal

Method used

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  • Ratiometric fluorescent probe for detecting hydrazine, and preparation method thereof
  • Ratiometric fluorescent probe for detecting hydrazine, and preparation method thereof
  • Ratiometric fluorescent probe for detecting hydrazine, and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Take 0.27g (1mmol) of 4-hydroxy-N-butyl-1,8-naphthalene diimide, add it to excess acetic anhydride, heat to reflux for 8h, and cool to room temperature. The reaction solution was poured into 100 mL of ice water, a large amount of precipitates were precipitated, filtered with suction, washed with a small amount of cold ethanol, and dried in vacuum to obtain a hydrazine molecular fluorescent probe.

[0029] 1 H NMR (600 MHz, DMSO- d 6 ): δ 8.52 (q, 2H), 8.43 (q, 1H), 7.90 (q, 1H), 7.69 (d, 1H), 4.04 (t, 2H), 2.52 (s, 3H), 1.62 (m, 2H ), 1.36 (m, 2H), 0.93 (t, 3H).

[0030] 13 C NMR (150 MHz, DMSO- d 6 ): δ 172.3, 166.6, 166.1, 154.7, 134.7, 134.5, 131.9, 131.4, 131.0, 128.2, 125.7, 123.4, 123.3, 33.0, 24.2, 23.1, 17.0.

[0031] Calculated HRMS (ESI): C 18 h 17 NO 4 [1+Na] + 334.1050; Found: 334.1054.

Embodiment 2

[0033] The hydrazine molecular fluorescent probe prepared in Example 1 was dissolved in DMSO to prepare a hydrazine molecular fluorescent probe standard solution with a concentration of 10 mmol / L.

[0034] Hydrazine was prepared into a stock solution of hydrazine molecules with a concentration of 1 mmol / L with distilled water.

[0035] Take 4, 8, 12, 20, 24, 28, 32, 36, 40, 60, and 80 μL of hydrazine molecule stock solution, respectively, add 2 μL of hydrazine molecule fluorescent probe standard solution, and use DMSO:PBS buffer (10 mM, pH = 7.4) = 1:1 (v / v) mixed solution was diluted to 2mL, and the concentration of fluorescent probe was prepared as 1×10 -5 M, hydrazine concentration 0.2~4×10 -5 A series of detection solutions of M, let stand at room temperature for 5 minutes, measure the fluorescence emission spectra of the series of detection solutions under the condition of fluorescence excitation wavelength of 300nm and slit width of 5nm / 5nm, take the wavelength as the a...

Embodiment 3

[0038] Take the hydrazine molecule stock solution of Example 2, and dilute it with a mixture of DMSO:PBS buffer (10mM, pH=7.4)=1:1 (v / v) to prepare 2×10 -6 M, 4×10 -6 M, 6×10 -6 M, 8×10 -6 M, 1×10 -5 Hydrazine standard solution of M.

[0039] Take 2 μL of the fluorescent probe standard solution of Example 2 and add it into a fluorescent cup, dilute it to 2 mL with the above-mentioned hydrazine standard solution of different concentrations, and let stand at room temperature for 5 minutes. Detect its fluorescence intensity under 543nm and 432nm wavelength respectively, take the concentration of hydrazine standard solution as abscissa, the ratio of fluorescence intensity at 543nm and 432nm place (I 543 / I 432 ) as the ordinate, we get figure 2 The standard curve diagram of the fluorescence response of the hydrazine molecular fluorescent probe reacted with different concentrations of hydrazine is shown.

[0040] Depend on figure 2 Visible, in 0~1×10 -5 Within the concen...

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Abstract

The invention discloses a ratiometric fluorescent probe for detecting hydrazine. The ratiometric fluorescent probe for detecting hydrazine is a derivative of 4-hydroxyl-N-butyl-1, 8-naphthalene diimide, with a structural formula of the derivative shown in the description and a molecular formula of C18H17NO4. The derivative of 4-hydroxyl-N-butyl-1, 8-naphthalene diimide is obtained by condensation of 4-hydroxyl-N-butyl-1, 8-naphthalene diimide and acetic anhydride. The fluorescent probe is used for realizing qualitative and quantitative detection and trace for hydrazine in a water environment system and a biological cell system, with high selectivity and high sensitivity, and has strong interference resistance.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a fluorescent probe capable of highly selective detection of hydrazine. Background technique [0002] Hydrazine is a chemical raw material with strong reducibility, widely used in synthesis, metal refining and other industries. Because of its high heat of combustion, it is also used as a formula for rocket fuel. However, studies have shown that hydrazine is also a neurotoxin, which can enter the human body through inhalation and skin contact, causing damage to the liver, kidney, lung and nervous system of the human body. The U.S. Environmental Agency (EPA) has classified hydrazine as a potential carcinogen with a threshold limit of 10ppb. Therefore, the development of a probe that can efficiently and specifically recognize and sense hydrazine both in vitro and in vivo is very important for the sustainable development of human health and the environment. [0003] There are many traditiona...

Claims

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Application Information

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IPC IPC(8): C07D221/14C09K11/06G01N21/64G01N21/78
CPCC07D221/14C09K11/06C09K2211/1029G01N21/6428G01N33/52
Inventor 孙玥段炼赵冬范善伟
Owner TAIYUAN UNIV OF TECH
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