CN113203779A - Magnetic Fe3O4Preparation of molecular imprinting electrochemical sensor and detection method of succinic acid - Google Patents
Magnetic Fe3O4Preparation of molecular imprinting electrochemical sensor and detection method of succinic acid Download PDFInfo
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Abstract
The invention researches a magnetic Fe3O4A preparation method of a molecular imprinting electrochemical sensor and a detection method of succinic acid belong to the field of electrochemical sensing. According to the invention, succinic acid is selected as a research object, a succinic acid magnetic molecularly imprinted polymer is synthesized for the first time, and the succinic acid magnetic molecularly imprinted polymer is combined with an electrochemical sensor technology, so that a novel high-sensitivity magnetic molecularly imprinted electrochemical sensor is successfully constructed. Firstly, synthesizing a magnetic molecularly imprinted polymer by a surface imprinting method, and then modifying the polymer on the surface of an electrode by a dripping coating method to be used as a recognition element to successfully construct a molecularly imprinted sensor. The molecular imprinting electrochemical sensor has high sensitivity and good selectivityThe method is successfully applied to the detection of succinic acid in actual samples.
Description
Technical Field
The invention belongs to the field of electrochemical sensing, and particularly relates to a magnetic molecularly imprinted polymer for detecting succinic acid, a preparation method and electrochemical characterization thereof.
Background
Succinic acid is an important intermediate product in a tricarboxylic acid cycle, and if the change of the succinic acid concentration in a fermentation liquid can be detected in real time in the glycolysis process, the aim of controlling the fermentation progress is expected to be fulfilled. At present, common succinic acid detection methods include high performance liquid chromatography, capillary electrophoresis, gas chromatography and the like, but the methods are difficult to achieve the purpose of detecting the succinic acid concentration in the fermentation process in real time, so that the discovery of a new method capable of monitoring the succinic acid concentration in real time has very important practical significance.
Although the traditional molecular imprinting technology has strong specificity and simple operation, the complicated centrifugal separation step consumes too much time when the traditional molecular imprinting technology is separated from a dispersion medium in the later period. The defect limits the application of the method in the fields of solid phase extraction, rapid detection and the like to a certain extent. In response to this disadvantage, Magnetic Molecular Imprinting (MMIT) technology has been developed. MMIT is a technique that combines magnetic nanomaterials with molecular imprinting techniques. The Magnetic Molecularly Imprinted Polymers (MMIPs) prepared by MMIT can specifically identify template molecules and can be quickly separated from a complex matrix by using an external magnetic field, so that the complicated step of separating the traditional MIPs by using centrifugal filtration is omitted, and the time of post-treatment is greatly saved.
The electrochemical sensor not only has high sensitivity and stability, but also is highly integrated, easy to miniaturize and simple to operate, and is favored by the majority of researchers. The magnetic molecular imprinting technology and the electrochemical sensing technology are combined, the selectivity of the electrochemical sensor can be effectively improved by preparing the molecular imprinting electrochemical sensor, and rapid and accurate trace detection of template molecules is realized.
Disclosure of Invention
The invention aims to provide a magnetic molecularly imprinted polymer capable of effectively identifying succinic acid molecules and a molecularly imprinted electrochemical sensor thereof.
The purpose of the invention is mainly realized by the following technical scheme:
1. magnetic molecular imprinting polymer membrane modified working electrode
1) A three-electrode system is adopted, a Glassy Carbon Electrode (GCE) is used as a working electrode, a platinum wire (Pt) is used as a counter electrode, and a Saturated Calomel Electrode (SCE) is used as a reference electrode. And (3) thoroughly cleaning the electrode, After the performance of the electrode is detected to be qualified, respectively dropwise adding a proper amount of the magnetic molecularly imprinted polymer dispersion liquid After elution and the magnetic molecularly imprinted polymer dispersion liquid Before elution on the surface of the electrode, and then placing the electrode in a room temperature environment for natural drying, wherein the magnetic molecularly imprinted polymer dispersion liquid After elution and the magnetic molecularly imprinted polymer dispersion liquid Before elution are marked as After-MIP/GCE and Before-MIP/GCE.
2) Respectively placing After-MIP/GCE and Before-MIP/GCE in succinic acid standard solution, adsorbing for a period of time, quickly taking out, washing the surface of the electrode with ultrapure water, and then placing in a room temperature environment for natural drying, wherein the A/After-MIP/GCE and the A/Before-MIP/GCE are recorded.
2. Electrochemical specific recognition and detection of succinic acid molecules
And (3) immersing the adsorbed electrode into a detection solution, detecting by adopting Differential Pulse Voltammetry (DPV), and recording the peak current value of the DPV. The method for synthesizing the succinic acid magnetic molecularly imprinted polymer by adopting the surface imprinting method comprises the following specific steps:
1) dissolving a certain amount of succinic acid, N '-isopropyl acrylamide (NIPAm), acrylamide (AAm) and a certain amount of methacrylic acid (MAA) in a certain amount of citric acid buffer solution, then adding a certain amount of N, N' -Methylene Bisacrylamide (MBA), and fully dissolving to obtain a solution A. Solution A was prepolymerized at room temperature for a certain time.
2) Taking a certain amount of Fe3O4The @ COOH magnetic nano particles are dissolved in a certain amount of citric acid buffer solution, and are dispersed for a certain time by ultrasonic to obtain a solution B.
3) And then uniformly mixing the solution A and the solution B, sequentially adding a certain amount of Ammonium Persulfate Solution (APS) and Tetramethylethylenediamine (TEMED), and mechanically stirring at room temperature for reacting for a certain time.
4) Collecting a polymerization product from the solution by an external magnetic field, and eluting the polymer by using a mixed solution of methanol and acetic acid with a certain proportion, thereby removing template molecules in the polymer and preparing the succinic acid Magnetic Molecularly Imprinted Polymer (MMIP). The procedure for the synthesis of non-imprinted polymers (NIP) was the same except that succinic acid was not added.
The invention adopts solvothermal method to synthesize Fe3O4The specific steps of the @ COOH magnetic nanoparticles are as follows:
1) weighing a certain amount of FeCl3·6H2Dissolving trisodium citrate in a certain amount of glycol, and performing ultrasonic treatment for a period of time to completely dissolve the trisodium citrate and the ethylene glycol.
2) Slowly adding a certain amount of anhydrous sodium acetate under mechanical stirring, and completely dissolving to obtain an orange-red solution.
3) Transferring the solution into a reaction kettle, and reacting at high temperature for a certain time. After the reaction is finished, cooling at room temperature, and collecting the synthesized reaction product Fe by magnetic separation3O4@ COOH magnetic nanoparticles were washed repeatedly with deionized water and ethanol.
The invention has the beneficial effects that:
1. the magnetic molecularly imprinted electrochemical sensor provided by the invention can be used for specifically identifying succinic acid molecules, and the construction method of the electrochemical sensor is expanded.
2. The magnetic molecularly imprinted electrochemical sensor provided by the invention can be used for quantitatively detecting succinic acid molecules and has wide practical application value.
3. The magnetic molecular imprinting electrochemical sensor provided by the invention has the advantages of simple and convenient construction method, low cost and easy industrial production; the detection steps are single, the requirement on the professional performance of operators is low, the popularization is easy, and the application prospect is wide.
Drawings
FIG. 1 is a Transmission Electron Micrograph (TEM) of a magnetic molecularly imprinted polymer
FIG. 2 is a graph of Cyclic Voltammetry (CV) of different modified electrodes in a detection solution
FIG. 3 is a graph of the alternating current impedance (EIS) of different modified electrodes in a test solution
FIG. 4 is a graph of the linear relation between the DPV response value and the succinic acid concentration of the magnetic molecular imprinting electrochemical sensor
Detailed Description
The following embodiments are further specific illustrations of the technical solutions of the present invention, but the present invention is not limited to the following embodiments.
Example 1: synthesis of succinic acid magnetic molecularly imprinted polymer
1) Certain amounts of succinic acid, N '-isopropylacrylamide (NIPAm), acrylamide (AAm), and certain amounts of methacrylic acid (MAA) were dissolved in certain amounts of citric acid buffer (pH 6.4), and then certain amounts of N, N' -Methylenebisacrylamide (MBA) were added and dissolved sufficiently to obtain solution a. Wherein N' -isopropylacrylamide (NIPAm): acrylamide (AAm): methacrylic acid (MAA): the molar ratio of N, N' -Methylene Bisacrylamide (MBA) is 5:1:1.5: 1-8: 5:3: 1. Solution A was prepolymerized at room temperature for 1 h.
2) Dissolving a certain amount of Fe3O4@ COOH magnetic nanoparticles in a certain amount of citric acid buffer (pH 6.4), wherein Fe3O4@ COOH magnetic nanoparticles: the mass ratio of the N, N' -Methylene Bisacrylamide (MBA) is 2: 1-5: 1. Ultrasonic dispersing for 10min to obtain solution B.
3) And then uniformly mixing the solution A and the solution B, and sequentially adding a certain amount of Ammonium Persulfate (APS) solution with the mass fraction of 10% and Tetramethylethylenediamine (TEMED), wherein N, N' -Methylene Bisacrylamide (MBA): ammonium persulfate: the molar ratio of the tetramethylethylenediamine is 3:2: 1-5: 4: 1. The reaction was stirred mechanically at room temperature for 24 h.
4) The polymerization product is collected from the solution by an external magnetic field, and the polymer is eluted by a mixed solution of methanol and acetic acid (9:1, V: V), so that the template molecules in the polymer are removed, and the succinic acid magnetic Molecularly Imprinted Polymer (MIP) is prepared. The procedure for the synthesis of non-imprinted polymers (NIP) was the same except that succinic acid was not added.
In the invention Fe3O4The specific steps of the @ COOH magnetic nanoparticles are as follows:
1) weighing certain mass of FeCl3·6H2O, trisodium citrate and anhydrous sodium acetate, wherein the mass ratio of the trisodium citrate to the anhydrous sodium acetate is 2:1: 2-6: 1: 7.
2) FeCl is added3·6H2Dissolving O and trisodium citrate in a certain amount of ethylene glycol, and ultrasonically dissolving.
3) And slowly adding anhydrous sodium acetate under mechanical stirring, and completely dissolving to obtain an orange-red solution.
4) The solution is transferred to a reaction kettle and reacted for 12 hours at 200 ℃. After the reaction is finished, cooling at room temperature, and collecting the synthesized reaction product Fe by magnetic separation3O4And @ COOH magnetic nanoparticles are repeatedly washed by deionized water and ethanol, and finally, the magnetic nanoparticles are subjected to vacuum freeze drying and then stored in a refrigerator at 4 ℃.
Example 2: preparation of succinic acid magnetic molecular imprinting sensor
1) 73mL of a 0.1mol/L citric acid solution and 127mL of a 0.1mol/L sodium citrate solution were mixed to prepare a citric acid buffer solution having a pH of 5.2.
2) And (3) dispersing a certain amount of the magnetic molecularly imprinted polymer into a certain volume of citric acid buffer solution (pH is 5.2) to obtain a magnetic molecularly imprinted polymer dispersion liquid with the concentration of 2-5 mg/mL.
3) And (3-8 mu L of magnetic molecularly imprinted polymer dispersion liquid is dripped on the surface of the glassy carbon electrode by adopting a dripping method to obtain the modified working electrode. The prepared electrode was named MIP/GCE.
Example 3: detection is carried out based on the molecularly imprinted electrochemical sensor prepared in example 2
1) Immersing the modified electrode into 5.0mmol/L [ Fe (CN)6]3-/4-And 0.5mol/L KCl, then performing electrochemical voltammetry scanning and alternating current impedance method measurement on each modified electrode, and obtaining a corresponding Cyclic Voltammetry (CV) diagram and an alternating current impedance (EIS) diagram after scanning.
2) The prepared electrochemical sensor was immersed in a standard solution containing succinic acid at various concentrations, and measured using Differential Pulse Voltammetry (DPV), and the solubility was plotted against the DPV response value.
3) Alpha-ketoglutaric acid, citric acid, malic acid and glucose are selected as interferents of succinic acid to determine the selectivity of the magnetic molecularly imprinted sensor.
As shown in FIG. 4, the peak current value and the succinic acid concentration showed good linear relationship in the range of 0.1-10mmol/L, and the linear regression equation was that I is 14.502LogC (mmol/L) +36.243 (R)2＝0.993)。
The above-mentioned embodiments are intended to illustrate the objects, technical solutions and advantages of the present invention, the embodiments of the present invention are not limited by the above-mentioned embodiments, and any modifications, equivalent substitutions, improvements, etc. made within the spirit and principle of the present invention are included in the protection scope of the present invention.
Claims (10)
1. A preparation method of a magnetic molecularly imprinted polymer for detecting succinic acid is characterized by comprising the following steps:
1) certain amounts of succinic acid, N '-isopropylacrylamide (NIPAm), acrylamide (AAm), and certain amounts of methacrylic acid (MAA) were dissolved in certain amounts of citric acid buffer (pH 6.4), and then certain amounts of N, N' -Methylenebisacrylamide (MBA) were added and dissolved sufficiently to obtain solution a. Solution A was prepolymerized at room temperature for 1 h.
2) Taking a certain amount of Fe3O4@ COOH magnetic nanoparticles were dissolved in a certain amount of citric acid buffer (pH 6.4) and ultrasonically dispersed for 10min to obtain solution B.
3) And then uniformly mixing the solution A and the solution B, sequentially adding a certain amount of Ammonium Persulfate (APS) solution with the mass fraction of 10% and Tetramethylethylenediamine (TEMED), and mechanically stirring at room temperature for reacting for 24 hours.
4) The polymerization product is collected from the solution by an external magnetic field, and the polymer is eluted by a mixed solution of methanol and acetic acid (9:1, V: V), so that the template molecules in the polymer are removed, and the succinic acid magnetic Molecularly Imprinted Polymer (MIP) is prepared. The procedure for the synthesis of non-imprinted polymers (NIP) was the same except that succinic acid was not added.
2. Fe of claim 13O4The preparation method of the @ COOH magnetic nanoparticles is characterized by comprising the following specific steps of:
1) weighing certain mass of FeCl3·6H2O, trisodium citrate and anhydrous sodium acetate, wherein the mass ratio of the trisodium citrate to the anhydrous sodium acetate is 2:1: 2-6: 1: 7.
2) FeCl is added3·6H2Dissolving O and trisodium citrate in a certain amount of ethylene glycol, and ultrasonically dissolving.
3) And slowly adding anhydrous sodium acetate under mechanical stirring, and completely dissolving to obtain an orange-red solution.
4) The solution is transferred to a reaction kettle and reacted for 12 hours at 200 ℃. After the reaction is finished, cooling at room temperature, and collecting the synthesized reaction product Fe by magnetic separation3O4And @ COOH magnetic nanoparticles are repeatedly washed by deionized water and ethanol, and finally, the magnetic nanoparticles are subjected to vacuum freeze drying and then stored in a refrigerator at 4 ℃.
3. The method for preparing a magnetic molecularly imprinted polymer for detecting succinic acid according to claim 1, wherein: n' -isopropylacrylamide (NIPAm) in the step 1): acrylamide (AAm): methacrylic acid (MAA): the molar ratio of N, N' -Methylene Bisacrylamide (MBA) is 5:1:1.5: 1-8: 5:3: 1.
4. The method for preparing a magnetic molecularly imprinted polymer for detecting succinic acid according to claim 1, wherein: fe in said step 2)3O4@ COOH magnetic nanoparticles: the mass ratio of the N, N' -Methylene Bisacrylamide (MBA) is 2: 1-5: 1.
5. The method for preparing a magnetic molecularly imprinted polymer for detecting succinic acid according to claim 1, wherein: n, N' -Methylenebisacrylamide (MBA) in the step 3): ammonium persulfate: the molar ratio of the tetramethylethylenediamine is 3:2: 1-5: 4: 1.
6. The method for preparing a magnetic molecularly imprinted polymer for detecting succinic acid according to claim 1, wherein: during elution in the step 4), the elution concentration range of MIP/NIP is guaranteed to be 0.5-1 mg/mL, and the elution solution is replaced every 5-8 h and is eluted for 2-3 times; and (3) freezing the eluted MIP/NIP in a refrigerator for 20 minutes, transferring the MIP/NIP into a vacuum freeze dryer for freeze drying for 5-7 hours, and then storing the MIP/NIP in a refrigerator at 4 ℃ for later use.
7. The molecularly imprinted electrochemical sensor prepared from the magnetic molecularly imprinted polymer according to claim 1, wherein the succinic acid molecule can be specifically detected by modifying the magnetic molecularly imprinted polymer membrane on the surface of the electrode.
8. The molecularly imprinted electrochemical sensor according to claim 7, wherein the dispersion of the magnetic molecularly imprinted polymer is dropped on the surface of the working electrode, and then the working electrode is naturally dried in a room temperature environment, and is labeled as MIP/GCE. The magnetic molecularly imprinted polymer dispersion liquid is obtained by dispersing a certain amount of magnetic molecularly imprinted polymer into a citric acid buffer liquid with a certain volume, and the concentration of the dispersion liquid is 2-5 mg/L.
9. The molecularly imprinted electrochemical sensor of claim 7, wherein the detection buffer is 5.0mmol/L [ Fe (CN)6]3-/4-And 0.5mol/L KCl, the detection method is Differential Pulse Voltammetry (DPV), the sensor can quantitatively detect the concentration of succinic acid molecules in the solution, the detection range is 0.1-10mmol/L, and the detection limit is 5.4x10- 3mmol/L。
10. The molecularly imprinted electrochemical sensor according to claim 7, wherein the difference between the electrochemical signals before and after the adsorption is the largest when the concentration of the magnetic molecularly imprinted polymer dispersion is 4mg/L and the dropping amount is 8 μ L and the adsorption time is 10 min.
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| CN114509479A (en) * | 2022-02-16 | 2022-05-17 | 云南大学 | Magnetic core-shell molecular imprinting material, preparation and application thereof, electrochemical sensor and application thereof, and ketamine detection method |
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Application publication date: 20210803 |