CN112147204B - Chlorpyrifos molecular imprinting photoelectrochemical sensor and preparation method thereof - Google Patents
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Abstract
The invention discloses a chlorpyrifos molecular imprinting photoelectrochemical sensor and a preparation method thereof. The preparation method of the photoelectrochemical sensor comprises the steps of coating the surface of a conductive substrate, preparing a BiOINFs/P3HT/ITO electrode by a SILAR method, dripping a mixed solvent of a cross-linking agent, a functional monomer and an initiator onto the surface of the electrode, heating and polymerizing to remove template molecules chlorpyrifos, and obtaining the MIP/BiOINFs/P3HT/ITO electrode after chlorpyrifos elution. The sensor is applied to chlorpyrifos detection in a water sample, has higher selective recognition capability, good reproducibility and stability, and is simple to manufacture and convenient to carry.
Description
Technical Field
The invention relates to a photoelectrochemical sensor and a preparation method thereof, in particular to a chlorpyrifos molecular imprinting photoelectrochemical sensor and a preparation method thereof.
Background
The chlorpyrifos, lese, chlorpyrifos is a high-efficiency poisoning organophosphorus pesticide, and the action mechanism of the chlorpyrifos, lese and chlorpyrifos is to destroy acetylcholinesterase in pests and cause cholinesterase dysfunction and even death, has good poisoning effect on phytophagous pests such as cabbage caterpillars, plant hoppers, rice leaf rollers and the like, is widely applied to vegetables, fruits and grain crops, but the ecological environment safety is seriously influenced by pesticide residues caused by excessive use, and threatens the life safety of people and animals. The limited use of organophosphorus pesticides and the prohibition of use of highly toxic organophosphorus pesticides are widely called for worldwide.
Since the organic phosphorus pesticide has high toxicity, it is very important to detect the residue of the organic phosphorus pesticide in environmental samples and agricultural products. There are some existing detection methods of instruments such as Gas Chromatography (GC), gas chromatography/mass spectrometry (GC/MS), liquid Chromatography (LC) and liquid chromatography/mass spectrometry (LC/MS), surface-enhanced raman spectroscopy, etc., which can provide higher sensitivity and specificity, and can determine various analogues at the same time, but there are also some disadvantages such as high cost, time consumption, high technical skill requirements, etc.
Disclosure of Invention
The invention aims to: the invention aims to provide a chlorpyrifos molecular imprinting photoelectrochemical sensor with high sensitivity, high response speed and simple instrument;
the invention further aims to provide a preparation method of the chlorpyrifos molecularly imprinted photoelectrochemical sensor.
The technical scheme is as follows: the chlorpyrifos molecular imprinting photoelectrochemical sensor comprises a reference electrode, an auxiliary electrode and a working electrode, wherein the working electrode is a molecular imprinting electrode, the molecular imprinting electrode comprises a conductive matrix and a composite material loaded on the conductive matrix, and the composite material is poly (3-hexylthiophene) -modified bismuth oxyiodide.
Preferably, the composite material is in a film layer structure on the conductive substrate, the lower layer of the film layer structure is a poly (3-hexylthiophene) film, and the upper layer is a bismuth oxyiodide film formed in situ on the poly (3-hexylthiophene) film.
Preferably, the method for forming the bismuth oxyiodide film in situ on the poly (3-hexylthiophene) film comprises the following steps: alternate immersion of poly (3-hexylthiophene) films into Bi (NO) by SILAR method 3 ) 3 Solutions and KI solutions.
Preferably, the thickness of the bismuth oxyiodide layer is 400-700nm.
Preferably, the poly (3-hexylthiophene) layer has a thickness of 300-500nm.
The preparation method of the chlorpyrifos molecularly imprinted photoelectrochemical sensor comprises the steps of constructing a three-electrode system by a reference electrode, an auxiliary electrode and a working electrode; the preparation method of the working electrode comprises the following steps:
(A) Dispersing poly (3-hexylthiophene) to obtain a suspension, coating the suspension on a conductive substrate, and drying to obtain a poly (3-hexylthiophene)/conductive substrate electrode;
(B) Alternately immersing poly (3-hexylthiophene)/conductive substrate electrode into Bi (NO) using SILAR method 3 ) 3 Preparing bismuth oxyiodide/poly (3-hexylthiophene)/conductive matrix electrode in the solution and the KI solution;
(C) Mixing template molecular chlorpyrifos, a cross-linking agent, a functional monomer and an initiator to obtain a mixed solution, dripping the mixed solution on the surface of a bismuth oxyiodide/poly (3-hexylthiophene)/conductive matrix electrode, carrying out polymerization reaction under the heating condition, and removing the template molecular chlorpyrifos to obtain the bismuth oxyiodide/poly (3-hexylthiophene)/conductive matrix molecularly imprinted electrode after chlorpyrifos elution.
Preferably, the Bi (NO 3 ) 3 .5H 2 The concentrations of the O and the KI solutions are 4-6 mmol/L.
Preferably, in step (B), the Bi (NO 3 ) 3 The time in the solution and the KI solution was 8-11 seconds, respectively.
Preferably, the cross-linking agent is ethylene glycol dimethacrylate, and the functional monomer is p-mercaptoaniline.
Preferably, in step (B), the poly (3-hexylthiophene)/conductive matrix electrode is selected from Bi (NO) 3 ) 3 The solution or KI solution is taken out, washed with water, and immersed in KI solution or Bi (NO 3 ) 3 In solution.
Preferably, in the step (A), the step of drying is to dry the coated conductive glass at 140-160 ℃ for 2-3 hours after naturally drying the conductive glass.
Preferably, in the step (C), the step of drying is to dry the dripped bismuth oxyiodide/poly (3-hexylthiophene)/conductive matrix electrode under vacuum for 3-5 h at 50-70 ℃.
Preferably, the cross-linking agent is ethylene glycol dimethacrylate, and the functional monomer is p-mercaptoaniline.
Preferably, prior to step (a), the conductive glass is subjected to a boiling treatment with an isopropanol solution of KOH.
The bandwidth of BiOI is 1.73-1.92eV, the bandwidth of poly (3-hexyltrypan) is 1.9-2.0eV, the poly (3-hexyltrypan) absorbs visible light to induce electrons to transit from the valence band to the conduction band, due to the synergistic effect caused by the close conduction band energies of the poly (3-hexyltrypan) and the BiOI, electrons in an excited state can be injected into the conduction band of the BiOI and then transferred to the surface of an electrode, so that photocurrent is increased, simultaneously, positive-charge holes can migrate from the valence band of the BiOI to the valence band of the poly (3-hexylthiophene), and then the holes react with water to generate hydroxyl radicals, and the hydroxyl radicals oxidize chlorpyrifos to generate chlorpyrifos radicals. Therefore, more chlorpyrifos free radicals can promote the further amplification of photocurrent, and therefore, the molecularly imprinted electrode manufactured by the material has higher sensitivity.
The beneficial effects are that: compared with the prior art, the invention has the following remarkable effects: 1. the synergistic effect of poly (3-hexylthiophene) and bismuth oxyiodide can further amplify photocurrent, so that the sensor provided by the invention has higher sensitivity for detecting chlorpyrifos, and is high in response speed, and the whole sensor device is simple in structure and easy to apply. 2. Bismuth oxyiodide is synthesized on the surface of poly (3-hexylthiophene) in situ, so that the two materials are combined more tightly, the stability of the whole electrode material is maintained, electrons in an excited state after the poly (3-hexylthiophene) absorbs visible light are injected into a conduction band of BiOI more easily, and the synergistic efficiency is improved; 3. by using an ethylene glycol dimethacrylate cross-linking agent and a P-mercaptoaniline functional monomer, a molecularly imprinted polymer with higher cross-linking degree can be formed on the surface of a BiOINFs/P3HT/ITO electrode; 4. the sensor can be applied to chlorpyrifos detection of water samples, and the concentration of chlorpyrifos is 1 multiplied by 10 -9 ～2.0×10 -7 In the range of mol/L,photocurrent intensity I-I 0 Concentration of chlorpyrifos C Chlorpyrifos (chlorpyrifos) The linear relation is good; 5. the sensor has high selective recognition capability, good reproducibility and stability, and is simple to manufacture and convenient to carry.
Drawings
FIG. 1 is a schematic diagram of the structure of the present invention;
FIG. 2 is a schematic flow chart of the preparation method of the invention;
FIG. 3 is a graph of photocurrents of chlorpyrifos tests of the present invention at different concentrations;
FIG. 4 is a graph showing the linear relationship between photocurrent intensity and chlorpyrifos concentration according to the present invention.
Detailed Description
The invention is described in further detail below with reference to the drawings.
Example 1
As shown in figure 1, the chlorpyrifos molecular imprinting photoelectrochemical sensor comprises a reference electrode, an auxiliary electrode and a working electrode, wherein the working electrode is a molecular imprinting electrode, the molecular imprinting electrode comprises a conductive matrix and a composite material loaded on the conductive matrix, and the conductive matrix Is Tin Oxide (ITO) conductive glass or other conductive matrixes. The composite material is poly (3-hexylthiophene) modified bismuth oxyiodide, the poly (3-hexylthiophene) is represented by P3HT, the bismuth oxyiodide is of a nano lamellar structure and is represented by BiOINFs, and therefore, the molecularly imprinted electrode is represented by MIP/BiOINFs/P3HT/ITO electrode, wherein MIP represents the molecularly imprinted electrode. The composite material is in a film layer structure on the conductive glass, the lower layer of the film layer structure is a P3HT film, and the upper layer is a BiOINFs film formed on the P3HT film in situ. The thickness of the BiOINFs film 2 is 400-700nm; the thickness of the P3HT film 3 is 300-500nm. The length of the BiOINFs film 2 and the P3HT film 3 is less than that of the conductive glass 1; specifically, the length of the biois film 2 and the length of the P3HT film 3 are equal, and the ratio of the length of the biois film 2 and the P3HT film 3 to the length of the conductive glass 1 is 0.8-1.2: 4 to 6. From fig. 1, it can be seen that the molecularly imprinted sites 4 are uniformly dispersed on the layered structure.
FIG. 2 is a schematic flow chart of a method for preparing the chlorpyrifos molecularly imprinted photoelectrochemical sensor, wherein a reference electrode, an auxiliary electrode and a working electrode are used for constructing a three-electrode system; the preparation method of the working electrode comprises the following specific steps:
(A) Preparation of P3HT/ITO electrode: cutting tin oxide (ITO) conductive glass into rectangular small pieces with length multiplied by width of 5cm multiplied by 0.6cm by a glass cutter, placing the rectangular small pieces in an isopropanol solution of 2mol/LKOH, boiling for 30min, taking out, ultrasonically cleaning for 10min, and placing the rectangular small pieces in a baking oven at 100 ℃ for later use. The poly (3-hexylthiophene) is synthesized by chemical oxidation polymerization with anhydrous ferric trichloride as an oxidant and 3-hexylthiophene as a monomer and chloroform as a solvent. 1mg of poly (3-hexylthiophene) was weighed and dispersed in 1mL of dimethylformamide solution, and sonicated for 15min to obtain 1mg/mL of poly (3-hexylthiophene) suspension. And (3) placing the treated ITO glass on a spin coater, uniformly spin-coating 25 mu L of 1mg/mL poly (3-hexylthiophene) suspension on the ITO glass by the spin coater, naturally air-drying, drying in a baking oven at 150 ℃ for 2.5h, and naturally cooling to obtain the P3HT/ITO electrode. Wherein P3HT is poly (3-hexylthiophene).
(B) Preparation of BiOINFs/P3HT/ITO electrode: 2 beakers were taken and each 5mmol/L Bi (NO) was prepared with ultrapure water 3 ) 3 .5H 2 O and 5mmol/L KI solution, immersing the P3HT/ITO electrode obtained in the step (1) into Bi (NO) 3 ) 3 Taking out the solution, washing with ultrapure water, immersing in KI solution, each immersing process lasts for 10s, and after certain SILAR circulation, preparing BiOINFs/P3HT/ITO, and naturally airing at room temperature. Wherein the SILAR method is a continuous ion layer adsorption reaction method.
(C) Preparation of MIP/BiOINFs/P3HT/ITO molecularly imprinted electrode: putting 5mL of toluene into a small beaker, adding 0.5mmol of chlorpyrifos, 0.5mmol of glycol dimethacrylate cross-linking agent, 1.0mmol of P-mercaptoaniline functional monomer and 0.040g of azodiisobutyronitrile initiator into the small beaker, uniformly mixing the materials by ultrasonic for 25min, taking 5 mu L of ultrasonic waves, mixing the mixed liquid, dripping the mixed liquid onto the surface of a BiOINFs/P3HT/ITO electrode, standing the mixed liquid at room temperature for 100s, uniformly forming a film on the surface of the electrode, then putting the electrode into a vacuum drying oven at 60 ℃, carrying out internal thermal polymerization for 5h, immersing the imprinting electrode into a mixed solution of methanol and acetic acid with the volume ratio of 9:1, removing the template molecular chlorpyrifos in the polymerized film, and obtaining the imprinting electrode MIP/BiOINFs/P3HT/ITO after chlorpyrifos molecule elution.
The MIP/BiOINFs/P3HT/ITO electrode prepared above is subjected to chlorpyrifos detection in a water sample:
5ml of 0.1mol/L PBS buffer solution with pH of 7.0 is taken, chlorpyrifos with a certain concentration is added into the buffer solution, the prepared MIP/BiOINFs/P3HT/ITO electrode is immersed into the buffer solution, the saturated calomel electrode SCE is used as a reference electrode,
a platinum wire of 1.0mm was used as an auxiliary electrode, and the photoelectric value was measured. Chlorpyrifos pesticide residues in water samples are measured by a photo-current-time curve (I-t).
MIP/BiOINFs/P in PBS solution 3 As shown in FIG. 3, the HT/ITO electrode pair with different concentrations of chlorpyrifos was measured to be 0.0 and 1.0X10 in PBS solution with 0.1mol/LpH of 7.0 for the MIP/BiOINFs/P3HT/ITO electrode pair -9 、5.0×10 -9 、1.0×10 -8 、2.0×10 -8 、4.0×10 -8 、6.0×10 -8 、8.0×10 -8 、1.0×10 -7 、1.5×10 -7 、2.0×10 -7 Photocurrent response of mol/L chlorpyrifos, wherein the different concentrations of chlorpyrifos are shown from bottom to top in fig. 3; the results showed that as chlorpyrifos concentration increased, the photoelectric value increased.
As shown in FIG. 4, chlorpyrifos concentration was 1X 10 -9 ～2.0×10 -7 Photocurrent intensity I-I in the mol/L range 0 The chlorpyrifos concentration C and chlorpyrifos have good linear relation, and the linear equation is as follows: I-I 0 -＝4.353+0.1644C Chlorpyrifos (chlorpyrifos) (R 2 =0.9962). When the signal-to-noise ratio is 3, the detection limit is 1.0X10 -10 mol/L(S/N＝3)。
And (3) measuring chlorpyrifos residue in the water sample by adopting the prepared MIP/BiOINFs/P3 HT/ITO:
surface water samples were taken for standard recovery experiments, see table 1. The result shows that the recovery rate of chlorpyrifos in a water sample is 96.1-107.5%, the sensor has good recovery rate in complex samples, the pretreatment of the method is simple, and the measurement result is good.
Table 1 determination of chlorpyrifos in water sample (n=6)
Example 2
The basic procedure is the same as in example 1, except that:
in the step (A), the poly (3-hexylthiophene) suspension is uniformly spin-coated on ITO glass by a spin coater, naturally air-dried, and then dried in an oven at 140 ℃ for 3 hours.
In step (B), bi (NO) 3 ) 3 .5H 2 The concentrations of the O and KI solutions are 4mmol/L; each immersion process lasted 8s;
in the step (C), the mixed solution is uniformly formed into a film on the surface of the electrode, and then the electrode is dried at a temperature of 50 ℃ for 5 hours.
Example 3
The basic procedure is the same as in example 1, except that:
in the step (A), the poly (3-hexylthiophene) suspension is uniformly spin-coated on ITO glass by a spin coater, naturally air-dried, and then dried in an oven at 160 ℃ for 2 hours.
In step (B), bi (NO) 3 ) 3 .5H 2 The concentrations of the O and KI solutions are 6mmol/L; each immersion process lasted 11s;
in the step (C), the mixed solution is uniformly formed into a film on the surface of the electrode, and then the electrode is dried for 3 hours at a temperature of 70 ℃.
Claims (6)
1. The chlorpyrifos molecular imprinting photoelectrochemical sensor comprises a three-electrode system consisting of a reference electrode, an auxiliary electrode and a working electrode, and is characterized in that the working electrode is a molecular imprinting electrode, the molecular imprinting electrode comprises a conductive matrix and a composite material loaded on the conductive matrix, and the composite material is poly (3-hexylthiophene) -modified bismuth oxyiodide;
the composite material is a film layer on the conductive matrixThe lower layer of the film layer structure is a poly (3-hexylthiophene) film (3), and the upper layer is a bismuth oxyiodide film (2) formed on the poly (3-hexylthiophene) film (3) in situ; the method for forming the bismuth oxyiodide film (2) on the poly (3-hexylthiophene) film (3) in situ comprises the following steps: alternately immersing poly (3-hexylthiophene) film (3) into Bi (NO) by SILAR method 3 ) 3 Solutions and KI solutions; the thickness of the bismuth oxyiodide film (2) is 400-700nm; the thickness of the poly (3-hexylthiophene) film (3) is 300-500 nm;
the template molecule of the molecularly imprinted electrode is chlorpyrifos; the positively charged holes can migrate from the valence band of bismuth oxyiodide to the valence band of poly (3-hexylthiophene), and then the holes react with water to generate hydroxyl radicals, which then oxidize chlorpyrifos to generate chlorpyrifos radicals, and more chlorpyrifos radicals are generated to promote further amplification of photocurrent.
2. A method for preparing a chlorpyrifos molecularly imprinted photoelectrochemical sensor in accordance with claim 1, which constructs a three-electrode system by a reference electrode, an auxiliary electrode and a working electrode, and is characterized in that the method for preparing the working electrode comprises the following steps:
(A) Dispersing poly (3-hexylthiophene) to obtain a suspension, and coating the suspension on a conductive substrate to obtain a poly (3-hexylthiophene)/conductive substrate electrode;
(B) Alternately immersing poly (3-hexylthiophene)/conductive substrate electrode into Bi (NO) using SILAR method 3 ) 3 Preparing bismuth oxyiodide/poly (3-hexylthiophene)/conductive matrix electrode in the solution and the KI solution;
(C) Mixing template molecular chlorpyrifos, a cross-linking agent, a functional monomer and an initiator to obtain a mixed solution, dripping the mixed solution on the surface of a bismuth oxyiodide/poly (3-hexylthiophene)/conductive matrix electrode, carrying out polymerization reaction under the heating condition, and removing the template molecular chlorpyrifos to obtain the bismuth oxyiodide/poly (3-hexylthiophene)/conductive matrix molecularly imprinted electrode after chlorpyrifos elution.
3. The method for preparing a chlorpyrifos molecularly imprinted photoelectrochemical sensor according to claim 2, wherein in the step (B), the Bi (NO 3 ) 3 .5H 2 The concentrations of the O and the KI solutions are 4-6 mmol/L.
4. The method for preparing a chlorpyrifos molecularly imprinted photoelectrochemical sensor according to claim 2, wherein in the step (B), the Bi (NO 3 ) 3 The time in the solution and the KI solution is 8-11 seconds respectively.
5. The method for preparing a chlorpyrifos molecular imprinting photoelectrochemical sensor according to claim 2, wherein the cross-linking agent is ethylene glycol dimethacrylate, and the functional monomer is p-mercaptoaniline.
6. The method for preparing a chlorpyrifos molecularly imprinted photoelectrochemical sensor according to claim 2, wherein in the step (B), the poly (3-hexylthiophene)/conductive base electrode is prepared from Bi (NO 3 ) 3 The solution or KI solution is taken out, washed with water, and immersed in KI solution or Bi (NO 3 ) 3 In solution.
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