Benzothiazole-cyanophenyl compound serving as hydrazine fluorescence probe as well as preparation method and application method of benzothiazole-cyanophenyl compound

A benzothiazole and fluorescent probe technology, applied in the fields of chemistry and fluorescent probes, can solve the problems of slow reaction rate and high detection limit of hydrazine fluorescent probes, and achieve the effects of simple preparation process and wide application prospects.

Active Publication Date: 2013-07-24
浙江富昇科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few fluorescent probes currently available for detecting hydrazine, and the detection limit of existing hydrazine fluorescent probes is still high, and the reaction rate is very slow (about 10-30 minutes)

Method used

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  • Benzothiazole-cyanophenyl compound serving as hydrazine fluorescence probe as well as preparation method and application method of benzothiazole-cyanophenyl compound
  • Benzothiazole-cyanophenyl compound serving as hydrazine fluorescence probe as well as preparation method and application method of benzothiazole-cyanophenyl compound
  • Benzothiazole-cyanophenyl compound serving as hydrazine fluorescence probe as well as preparation method and application method of benzothiazole-cyanophenyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Synthesis of the fluorescent probe 4-(4-benzothiazolylphenyl)ethynylstyrene dinitrile (compound I) when R is ethynyl.

[0029] (1) Add 0.46g (2.5mmol) p-bromobenzaldehyde and 0.31g (2.5mmol) o-aminothiophenol into 25mL triethyl phosphate, stir for 10min, add 2.5mL glacial acetic acid, stir rapidly and heat up to 60 ℃, add 1.8g (3.75mmol) lead tetraacetate, stir for 30 minutes and cool to room temperature, add 100mL water and 50mL dichloromethane, separate the liquid, collect the organic phase, and extract the aqueous layer three times with dichloromethane (50mL×3) , collect and combine the organic phases, dry with anhydrous magnesium sulfate, evaporate the solvent to dryness, separate and purify the obtained solid by 100-200 mesh silica gel column chromatography (dichloromethane:petroleum ether=1:2), and obtain the product 2-(4 -bromophenyl)benzothiazole 0.46g, yield 63%. Its melting point was measured to be 137.2°C.

[0030] (2) 1.44g (5mmol) 2-(4-bromophenyl) benzot...

Embodiment 2

[0036] Example 2: The response of the fluorescence spectrum of the fluorescent probe 4-(4-benzothiazolylphenyl)ethynylstyrene dinitrile (compound I) to the concentration of hydrazine.

[0037] Use THF and water 1:1 solution to prepare solutions with hydrazine concentrations of 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, 110, 120, 130nM and hydrazine-free solutions, taking the above differences Concentration value of hydrazine solution 5mL, were added with a concentration of 1 × 10 -4 Take 50 μL of compound I solution in THF and water at a volume ratio of 1:1, shake it evenly, and test its fluorescence spectrum. The test conditions are: the excitation wavelength is 395nm, the slit width is 2.5nm / 2.5nm, and the voltage is 700V. Test results such as figure 1 with figure 2 shown.

[0038] from figure 1 It can be clearly found that when the hydrazine concentration in the solution is lower than 130nM, the fluorescence emission peak intensity of the fluorescent probe 4-(4-benzothi...

Embodiment 3

[0040] Example 3: The fluorescence spectrum of the fluorescent probe 4-(4-benzothiazolylphenyl)ethynylstyrene dinitrile (compound I) responds to hydrazine in the presence of interfering ions.

[0041] Prepare a mixed solution of THF and water at a ratio of 1:1, and use this solution to prepare Ni with a concentration of 1mM 2+ , Ca 2+ , Mg 2+ 、Al 3+ , Zn 2+ 、K + , Pb 2+ 、Co 2+ 、Cd 2+ 、Cr 2+ 、Cu 2+ and Na + ionic solution, and 5 mL each was added to it with a concentration of 1×10-4M compound I mixed with THF and water at a volume ratio of 1:1, 50 μL, and the fluorescence spectrum was tested after shaking evenly. The test conditions are: the excitation wavelength is 395nm, the slit width is 2.5nm / 2.5nm, and the voltage is 700V. Test results such as image 3 shown.

[0042] from image 3 It can be seen that when the solution does not contain hydrazine, the fluorescence intensity of the probe does not change significantly before and after adding various common metal...

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Abstract

The invention discloses a benzothiazole-cyanophenyl compound serving as a hydrazine fluorescence probe. The benzothiazole-cyanophenyl compound has a structural formula as shown in (I); the compound is prepared by performing cyclodehydration with bromobenzaldehyde and 2-amino-4-chloro thiophenol serving as the raw materials, then performing coupled reaction in order to connect with a bromobenzaldehyde derivate, and finally performing Knoevenagel reaction with malononitrile. The benzothiazole-cyanophenyl compound has the advantages that the raw materials are low in price and easy to gain, the synthetic route is simple, and the yield is relatively high; rigid structures such as benzothiazole and phenylacetylene groups are introduced into such a fluorescence probe, thus high fluorescence quantum efficiency is realized, and relatively high thermal stability and dissolubility are brought. The probe adopts the photoinduced charge transfer mechanism and the conjugate passivation mechanism, therefore, a response range respect to hydrazine can be expanded; the probe has the characteristics of being fast in response, high in sensitivity and high in selectivity, is suitable for being applied to safety detection of foods as well as safety detection of a laboratory, in particular applied to industrial wastewater monitor; and the probe has a wide application prospect in environment monitoring, ecological protection, disease diagnosis, industrial production and pollution discharge inspection.

Description

technical field [0001] The invention relates to a hydrazine fluorescent probe benzothiazole-benzonitrile compound and a preparation method thereof, belonging to the fields of chemistry and fluorescent probes. Background technique [0002] In recent years, medical research has found that hydrazine has carcinogenic effects, and long-term exposure can lead to gene mutations. However, as a strong reducing agent and foaming agent, hydrazine has been widely used in chemical synthesis, physics, and industrial production in the past few decades. Especially in industrial production, hydrazine is often used in large quantities as Foaming agents and antioxidants have caused great pressure on the environment and ecological protection. In addition, hydrazine is also a kind of rocket fuel, which is flammable and explosive under dry conditions. Therefore, the detection of hydrazine is of great significance. [0003] The methods currently available for measuring hydrazine generally inclu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/66G01N21/64
Inventor 钱国栋谭轶群杨雨崔元靖郁建灿王智宇樊先平王民权
Owner 浙江富昇科技有限公司
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