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Benzothiazole-aniline compound used as pH fluorescent probe and preparation method thereof

An aniline compound, benzothiazolyl phenyl technology, applied in the field of chemistry, can solve the problems of unstable luminophore, proton concentration sensitivity, poor selectivity, etc., and achieves the effect of wide application prospect and simple preparation process

Active Publication Date: 2014-07-02
浙江富昇科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the measurement range of common pH fluorescent probes is concentrated between 4 and 9. This is because traditional pH fluorescent probes are often based on luminophores that are unstable under strong acidic conditions, such as coumarin or fluorescein, and are sensitive to protons. Concentration is very sensitive, when the proton concentration is low (that is, when the pH is around 7), it will generate a fluorescent signal and reach saturation
Due to the addition of too many proton sensing groups, the few fluorescent probes with fluorescent response under low pH conditions have a non-linear relationship between fluorescence intensity and pH value, so accurate pH measurement cannot be performed, and the selectivity is poor.

Method used

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  • Benzothiazole-aniline compound used as pH fluorescent probe and preparation method thereof
  • Benzothiazole-aniline compound used as pH fluorescent probe and preparation method thereof
  • Benzothiazole-aniline compound used as pH fluorescent probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of fluorescent probe 4-(4-benzothiazolylphenyl)ethynylaniline (compound I).

[0032]

[0033] (1) Synthesis of 2-(4-bromophenyl)benzothiazole

[0034] 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°C, add 1.8g (3.75mmol) lead tetraacetate, stirred for 30 minutes, cooled to room temperature, added 100mL water and 50mL dichloromethane, separated, collected the organic phase, extracted the aqueous layer with dichloromethane three times (50mL×3), collected and combined The organic phase was dried with anhydrous magnesium sulfate, the solvent was evaporated to dryness, and the obtained solid was separated and purified by 100-200 mesh silica gel column chromatography (dichloromethane: petroleum ether = 1:2) to obtain the product 2-(4-bromobenzene Base) benzothiazole 0.46g, yield 63%. Its melting point was measured...

Embodiment 2

[0045] Example 2: Response of fluorescence spectrum of fluorescent probe 4-(4-benzothiazolylphenyl)ethynylaniline (compound I) to pH.

[0046] Use Britton-Robinson buffer solution to prepare a buffer solution with a pH value of 4.35-1.81, and use HCl and NaOH to prepare a solution with a pH value of 0.3-1.81 to obtain industrial wastewater with a simulated pH value in the range of 0.3-4.35. Each solution was 5mL, and the concentration was 1×10 -4 Mix 50 μL of DMF solution of compound I of M, and test its fluorescence spectrum after shaking evenly. The test conditions are: the excitation wavelength is 340nm, the slit width is 5nm / 5nm, and the voltage is 700V. Test results such as figure 1 and figure 2 shown.

[0047] from figure 1 It can be clearly found that when the pH value of the solution is lower than 4.35, the fluorescence emission peak intensity of the pH fluorescent probe 4-(4-benzothiazolylphenyl)ethynylaniline increases gradually with the decrease of the solutio...

Embodiment 3

[0049] Example 3: The response of the fluorescence spectrum of the fluorescent probe 4-(4-benzothiazolylphenyl)ethynylaniline (compound I) to pH in the presence of interfering ions.

[0050] Use Britton-Robinson buffer solution to prepare a buffer solution with a pH value of 4.35, use HCl and NaOH to adjust and configure a solution with a pH value of 1.05, and use the above two solutions with different pH values ​​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 5mL were added to it with a concentration of 1×10 -4 Mix 50 μL of DMF solution of compound I of M, and test its fluorescence spectrum after shaking evenly. The test conditions are: the excitation wavelength is 340nm, the slit width is 5nm / 5nm, and the voltage is 700V. Test results such as image 3 shown.

[0051] from image 3 It can be seen from the figure that when the pH value of the solution is 4.35, the ...

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Abstract

The invention discloses a benzothiazole-aniline compound used as a pH fluorescent probe and a preparation method thereof. The structural formula is shown as a chemical formula (shown in the description) (I), wherein in the formula, R1 is vinyl, acetenyl, styryl, phenylethynyl, biphenyl or perylene base; and R2 and R3 are both hydrogen, methyl or ethyl alkane. The preparation method comprises the following steps of: taking p-bromobenzaldehyde and 2-aminothiophenol as raw materials, and connecting with iodine-containing nitrobenzene derivative through dehydration cyclization reaction and coupling reaction; and generating the pH fluorescent probe benzothiazole-aniline derivative through reductive amination. Rigid structures, such as benzothiazole and phenylethynyl, are introduced into the fluorescent probe; the fluorescent probe is high in fluorescence quantum efficiency, and high in thermal stability and solubility. The probe can detect pH value under strong acid condition by adopting a photoinduced charge transfer mechanism and a conjugate passivation mechanism; and the probe has the characteristics of rapid response, high sensitivity and high selectivity, and has wide application prospect in environment monitoring, ecological protection, disease diagnosis, industrial production and sewage inspection.

Description

technical field [0001] The invention relates to the fields of chemistry and fluorescent probes. Background technique [0002] As a measure of acidity, pH value is an important parameter in environmental protection, human health, biophysiology, chemistry, physics, mining, and industrial production. Especially in industrial production, a large amount of strong acidic industrial wastewater is often produced. Environmental and ecological protection has caused great pressure, so it is of great significance to accurately measure the pH value, especially the pH value of strongly acidic aqueous solutions. [0003] The commonly used methods for measuring pH value mainly include pH test paper measurement method, electrode method and fluorescent probe measurement method. Among them, the pH test paper measurement method has a low degree of accuracy and is greatly affected by subjective factors, which is not conducive to accurate measurement of pH value. Compared with the pH test paper...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/66C09K11/06G01N21/64
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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