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Functional reactive dye for zinc ion probe, and preparation method and application thereof

A reactive dye and functional technology, applied in reactive dyes, dyeing methods, azo dyes, etc., can solve the problems of not indicating the ion detection range, etc., and achieve the effects of low cost, good selectivity, and high yield

Inactive Publication Date: 2016-03-16
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After reviewing a large number of patents, it is found that there are almost no patents that indicate the relationship between the probe and ion concentration, and do not indicate the detection range of ions.

Method used

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  • Functional reactive dye for zinc ion probe, and preparation method and application thereof
  • Functional reactive dye for zinc ion probe, and preparation method and application thereof
  • Functional reactive dye for zinc ion probe, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] (1) Synthesis of rhodamine B hydrazide

[0042] Take a 100mL three-neck flask, weigh 1.200g (2.5mmol) Rhodamine B and dissolve it in 30mL absolute ethanol, stir vigorously at room temperature and slowly add 1mL (19.8mmol excess) 98% hydrazine hydrate dropwise. Heat to reflux at 78°C for 2 hours until the solution turns from dark purple to clear yellow. After the reaction is completed, cool to room temperature, and use a rotary evaporator to evaporate the solvent and excess hydrazine hydrate to obtain a light yellow crude product of rhodamine B hydrazide. Take 50mL of newly prepared 1M HCl and add it to the crude product, and the product dissolves into a pink solution. Slowly add 1M NaOH to the solution under stirring to adjust the pH value to between 9-10. When NaOH was added dropwise to the mixed solution, when the pH of the solution was adjusted to about 6, pale pink flocculent precipitates began to precipitate out. Filter and wash the precipitate with 15ml deioniz...

Embodiment 2

[0049] Synthesis of Functional Reactive Dyes as Zinc Ion Probes

[0050] Take a 250ml three-necked flask, dissolve 603mg (1.00mmol) R1 in 20mL of anhydrous THF, stir in the three-necked flask and place it in an oil bath, N 2 Under protection, the temperature was maintained at 42°C. Weigh 0.16gNaHCO 3 Add to the mixed solution as an acid-binding agent to control the pH value of the system. Take 268 mg (1.00 mmol) of 4-aminosalicylaldehyde benzoylhydrazone P, dissolve it in 40 ml of THF, and slowly drop it into a three-necked flask while stirring. The reaction was carried out under reflux and stirring at 50°C for six hours, followed by TLC running until the reaction of the raw materials was complete. The filtrate was rotary evaporated to remove the solvent, the solid product was washed with a small amount of distilled water several times, and dried in a vacuum drying oven to constant weight to obtain the final product of functional reactive dye of zinc ion probe. figure 2 D...

Embodiment 3

[0055] Add different concentrations of zinc ions to the DMF solution, such as image 3 As indicated, the fluorescence intensity of the liganded fluorescent probe (10 μM) was measured at an excitation wavelength of 372 nm. When adding only 10nM concentration of zinc ions to the fluorescent probe (10μM) solution, the fluorescent probe solution presents a fluorescence emission peak at around 483nm, with the Zn 2+ The intensity of the fluorescence emission peak at 483nm was also significantly enhanced with the increase of ion concentration. When Zn 2+When the ion concentration reaches 10μM, the fluorescence intensity of the ligand fluorescent probe hardly changes with the increase of ion concentration. In the DMF solution of fluorescent probe R2, different metal ions (Zn 2+ 、Cd 2+ 、Sr + 、Cr 3+ , Fe 3+ 、Co 2+ 、Ni 2+ 、Cu 2+ 、Na + 、Ba 2+ , Mn 2+ , Ca 2+ , Pb 2+ , Sn 2+ 、 Bi + , Hg 2+ ) for selective interference detection. Figure 4 It can be seen from the results ...

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Abstract

The invention relates to a functional reactive dye for a zinc ion probe, and a preparation method and application thereof. The dye has a structural formula as described in the specification. The preparation method comprises the following steps: subjecting rhodamine B and hydrazine hydrate to a heating reflux reaction so as to obtain rhodamine B hydrazide; subjecting methyl p-aminobenzoate and hydrazine hydrate to a heating reflux reaction, dissolving a product in a solvent, adding salicylaldehyde drop by drop and then carrying out a heating reflux reaction so as to obtain salicylaldehyde-4-aminobenzoyl hydrazone; and dissolving cyanuric chloride in a solvent, adding an acid binding agent, adding rhodamine B hydrazide drop by drop at a temperature in a range of -5 to 5 DEG C, carrying out a reaction under stirring so as to obtain a concentration product, dissolving the concentration product in a solvent, adding the acid binding agent, adding salicylaldehyde-4-aminobenzoyl hydrazone drop by drop and carrying out a reflux reaction with temperature controlled so as to obtain the functional reactive dye. The functional reactive dye has good selectivity on zinc ions, is convenient to use in sewage treatment and exerts good usage effect.

Description

technical field [0001] The invention belongs to the field of functional reactive dyes and their preparation, in particular to a functional reactive dye of a zinc ion probe and its preparation method and application. Background technique [0002] As one of the most abundant transition metal ions in living cells, zinc ion plays a very important role in many physiological and pathological processes, such as gene expression, metalloenzyme regulation, nerve signal transduction, cell apoptosis, DNA binding and recognition, etc. effect. In addition, zinc, as a major environmental pollutant metal ion, may lead to the destruction of microbial systems in soil in excess. At the same time, it is also a common pollutant in agricultural products and food. Therefore, when zinc ions exceed the standard, it will lead to environmental pollution and excess zinc ions in food. Zinc plays a role in regulating the immune function of the human body, and can maintain normal physiological functions...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B62/04C09K11/06D06P1/382G01N21/64
CPCC09B62/046C09K11/06C09K2211/1022C09K2211/1029C09K2211/1059C09K2211/1088D06P1/382G01N21/643
Inventor 光善仪魏刚张月华徐洪耀
Owner DONGHUA UNIV
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