CN105044177A - Method for preparing molecularly imprinted paper chip sensor through click chemistry technology - Google Patents
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Abstract
The invention discloses a method for preparing a molecularly imprinted paper chip sensor through the click chemistry technology. The Adobe Illustrator CS4 is adopted for designing paper chip printing patterns, a wax springing printer is adopted for printing patterns in batches to paper, heating and wax melting are carried out to manufacture a hydrophobic wall, a working electrode, a reference electrode and a counter electrode are printed through the screen printing technology, and gold nanoparticles grow on the paper filter surface by the adoption of a seed growth method. Azide alkyl mercaptan is fixed to the paper fiber gold nano material surface and subjected to a click chemistry reaction with propargyl acrylate, a functional monomer of synthetic organophosphorus pesticide molecularly imprinted polymer is selected, template molecules, the functional monomer, quantum dots, the cross-linking agent, the pore-foaming agent, the initiator and the organic solvent of organophosphorus pesticides are evenly mixed according to a certain substance amount, a polymerization reaction is induced under 365nm ultraviolet light, and a paper fiber surface molecularly imprinted polymer film is prepared. High-selectivity, high-sensitivity, low-cost and real-time-detection for organophosphorus pesticide is achieved by the adoption of a photoinduced electricity chemical method.
Description
Technical field
The present invention relates to the Detection Technologies of Pesticide Residues field, be more particularly a kind of photic galvanochemistry paper chip sensor preparation that can detect organophosphorus pesticide, the invention still further relates to the method for trace residues of pesticides in the molecular imprinting working sample described in employing.
Background technology
Agricultural chemicals is widely used in the class organic compound controlling or eliminate agricultural, forestry pests & diseases, and because Pesticide use increasing extent is wide, frequency of utilization is more and more higher, and amount of application is increasing, has become the agricultural chemicals that contaminated food products is the most serious.Residues of pesticides exceed standard and not only pollute agricultural product and ecologic environment, also will jeopardize health and life security.Organophosphorus pesticide is the agricultural chemicals that in current agricultural chemicals, a class is widely applied, organophosphorus pesticide is with body, inhibiting effect is had to cholinesterase in biosome, cholinesterase is suppressed to make it lose the ability of decomposing acetylcholine, acetylcholine is caused to accumulate, cause nerve dysfunction, thus cause the infringement to human body.
Set up a kind of method of high sensitivity and specific Rapid Screening organophosphorus pesticide thing, just become one of this research field problem needing solution badly current.Current existing organophosphorus pesticide quality testing survey or screening methods mainly comprise and mainly comprise chromatography, inhibiting AChE, immunological method etc., but these detect or screening methods Shortcomings.
Thin-layered chromatography is simple to operate, be convenient to grasp, accurately qualitative, but quantitative measurement accuracy and sensitivity low, be a kind of conventional qualitative determination method.Although chromatography mass spectrometry detection sensitivity is very high but price is relatively costly, and chromatography detection limit is higher, the actual needs of trace residues of pesticides and export trade detection can not be met, therefore usually need before analysis to carry out enrichment, the difficult point of the separation and purification of complicated food and agricultural product is that sample substrate is complicated, interfering material is many, and pre-treatment step is more loaded down with trivial details.
Inhibiting AChE is easy and simple to handle, and speed is fast, does not need expensive instrument, be particularly suitable for the selective mechanisms of Site Detection and gross sample, but sensitivity is poor, and different to the sensitivity of all kinds of different detection of organic phosphorus pesticide, and repeatability, the recovery need to improve.
Enzyme-linked immune analytic method detects the highly sensitive of organophosphorus pesticide, degree of accuracy is high, the high specificity of method, convenient and swift, but it is high to the selectivity of reagent, will synthesize corresponding artificial antigen when small-molecule substance is detected, not only workload is large for hapten synthesis, the cycle is long, and cross reaction in various degree may be there is in the agricultural chemicals of similar or pesticide metabolism thing to be measured.
For several detection methods of organophosphorus pesticide in food, compare and respectively have quality, wherein for requiring that in detection of organic phosphorus pesticide detection sensitivity is high, sample handling processes wants simple, processing speed is fast, operative installations is little, wanting high to the selectivity and the recovery that measure component in advance.In the case, new detection technique or sample pretreating method are developed by positive, molecular engram paper chip photic electrochemical sensor preparation and for detection of organic phosphorus pesticide.
Summary of the invention
The object of this invention is to provide click chemistry technology and prepare molecular engram paper chip sensor, the present invention adopts paper chip to be carrier, utilize click chemistry technology for preparing molecular blotting ploymer film, establish the photic galvanochemistry paper chip sensor method for quick of organophosphorus pesticide, successfully establish sensitive, quick, special, the on-the-spot instant sensor detecting organophosphorus pesticide.
In order to solve the problems of the technologies described above, the present invention is realized by following measures: click chemistry technology prepares molecular engram paper chip sensor, it is characterized in that comprising the following steps:
(1) design paper chip hydrophobic wax bulk print pattern with AdobeIllustratorCS4 on computers, paper as shown in Figure 1, is cut into A4 size by pattern, is placed into by the paper cut out in wax spray printer, and hydrophobic wax bulk print pattern prints on paper;
(2) paper with wax pattern in step (1) is placed in constant temperature oven, under 60-150 degree Celsius, heats 0.5-2 minute;
(3) at paper base material hydrophilic region by screen printing technique printing work electrode, contrast electrode and to electrode;
(4) batch paper chip after step (3) process is cut into single paper chip, gold seeds solution drops to the back side hydrophilic region being printed on working electrode, hatch 0.5 ~ 1h, add the phosphate buffer solution that 20 μ L contain gold chloride, hexadecyltrimethylammonium chloride and hydrogen peroxide, hatch 5 ~ 10 minutes, paper fiber surface growth gold nano grain;
(5) paper fibers gold Nanosurface fixes alkyl azide mercaptan, and 10 μ L ~ 15 μ L2mmol/L nitrine undecyl mercaptan drip hatches 8 ~ 12h in paper chip perform region, and then use redistilled water washes clean, nitrogen dries up;
(6) by reacting with acrylic acid propynyl ester click chemistry, 5 μ L ~ 10 μ L2mmol/L acrylic acid propynyl ester solution are added to the working electrode area that step (5) processed, and add 0.5mol/L ascorbic acid and 0.1mol/L copper sulphate mixed liquor 10 μ L, lucifuge places 10h, first use methanol wash, then second distillation water washing, dries;
(7) function monomer of synthesis organophosphorus insecticide molecular imprinted polymer membrane is selected;
(8) existing method is utilized to prepare semiconductor-quantum-point material;
(9) mix than by the template molecule of organophosphorus insecticide, function monomer, quantum dot, crosslinking chemical, pore-foaming agent, initiating agent and organic solvent by certain amount of substance, under 365nm ultraviolet light, induced polymerization reaction 1h, prepares paper fiber surface molecular imprinted polymer membrane;
(10) by template molecule in eluent molecular imprinted polymer membrane, then successively with ethanol, distilled water wash respectively 3 times, for subsequent use;
(11) by sample drop in paper chip, place 5 ~ 10 minutes, adopt distilled water wash 3 times, detect, as shown in Figure 2.
Paper of the present invention is the Whatman chromatographic paper of GEHealthcareWorldwide company of Chinese Shanghai Pudong;
Wax spray printer of the present invention is Fuji-Xerox's wax spray printer;
Working electrode of the present invention adopts carbon printing, contrast electrode Ag/AgCl prints and prints electrode carbon;
Gold seeds solution of the present invention adopts sodium borohydride reduction, sodium citrate is that protective agent obtains;
Phosphate buffer solution concentration of the present invention is that 10mmol/L contains 1.2mmol/L gold chloride, 2.0mmol/L hexadecyltrimethylammonium chloride and 7.2mmol/L hydrogen peroxide;
Of the present invention for semiconductor-quantum-point be CdTe quantum, CdSe quantum dot and CdS quantum dot;
Function monomer of the present invention is Methacrylamide, acrylamide, acrylic acid, methacrylic acid;
Crosslinking chemical of the present invention is ethylene glycol dimethacrylate;
Initiating agent of the present invention is azoisobutyronitrile, potassium persulfate;
Pore-foaming agent of the present invention adopts acetonitrile, methyl alcohol, isopropyl alcohol;
Organic solvent of the present invention is methylene chloride or phenixin;
The amount of substance ratio of the template molecule of synthetic pesticide remaining molecules imprinted polymer film of the present invention, function monomer, crosslinking chemical, pore-foaming agent, initiating agent and organic solvent is 0.1 ~ 0.5: 5: 0.5 ~ 5: 20 ~ 55: 0.1 ~ 0.5: 1.5 ~ 30, mixes 2mg quantum dot;
Eluant, eluent of the present invention is the ethanol/acetone of volume ratio 8:2.
Click chemistry technology of the present invention prepares molecular engram paper chip sensor, beneficial effect of the present invention:
1. molecular engram photic galvanochemistry paper chip sensor preparation method, chemically grown method paper fiber grows golden nanometer particle, increase the specific surface area of sensing interface and the electric conductivity of paper fiber, make prepared pesticide residue molecular engram photic galvanochemistry paper chip sensor have higher sensitivity and sensing range.
2. adopting click chemistry technology will prepare molecular engram film being modified with Jenner's rice paper fiber surface, improve selectivity and the accuracy of photic galvanochemistry paper chip sensor.
3. the present invention obtain photic galvanochemistry paper chip sensor and utilize quantum dot to carry out effective separation of photocurrent carrier, the highly sensitive detection of sample Pesticide Residues thing can be realized.
4. the photic electrochemical analysis method of employing of molecular engram of the present invention photic galvanochemistry paper chip sensor, can improve the highly sensitive of method, simplifies instrument and equipment, improves detection speed, can realize the high flux screening of great amount of samples at short notice.
5. molecular engram of the present invention photic galvanochemistry paper chip sensor completes detection pesticide residue in paper chip, greatly reduces running cost, is convenient to Site Detection.
Accompanying drawing explanation
Fig. 1 paper chip pattern and the pattern that prints electrode, A: auxiliary area, B: perform region, C: to electrode, D: working electrode, E: contrast electrode.
Fig. 2 molecular engram paper chip sensor detects schematic diagram.
Embodiment
embodiment 1: the detection of parathion-methyl
(1) design paper chip hydrophobic wax print pattern with AdobeIllustratorCS4 on computers, be placed into by the paper cut out in wax spray printer, hydrophobic wax print pattern prints on paper;
(2) paper with wax pattern in step (1) is placed in constant temperature oven, heats 1.5 minutes under 90 degrees Celsius;
(3) printed electrode by screen printing technique at paper base material hydrophilic region, working electrode adopts carbon slurry, contrast electrode Ag/AgCl slurry and adopts carbon slurry to electrode;
(4) batch paper chip after step (3) process is cut into single paper chip, 10 μ L gold seeds solution drop to the back side hydrophilic region being printed on working electrode, hatch 1h, add the 10mmol/L phosphate buffer solution that 20 μ L contain 1.2mmol/L gold chloride, 2.0mmol/L hexadecyltrimethylammonium chloride and 7.2mmol/L hydrogen peroxide, hatch 8 minutes, paper fiber surface growth gold nano grain;
(5) paper fibers gold Nanosurface fixes alkyl azide mercaptan, and 10 μ L2mmol/L nitrine undecyl mercaptan hatch 10h at paper chip electrode, and then use redistilled water washes clean, nitrogen dries up;
(6) by reacting with acrylic acid propynyl ester click chemistry, 5 μ L2mmol/L acrylic acid propynyl ester solution are added to the working electrode area that step (5) processed, and add 0.5mol/L ascorbic acid and 0.1mol/L copper sulphate mixed liquor 10 μ L, lucifuge places 10h, first use methanol wash 3 times, then second distillation water washing 3 times, dries;
(7) CdTe quantum solution preparation: at N
2under protection, be Te presoma by the NaHTe of existing system, with CdCl
2reaction, mercaptoacetic acid as under the condition of stabilizing agent, the water-soluble CdTe quantum dots solution of system;
(8) by parathion-methyl, acrylamide, ethylene glycol dimethacrylate, acetonitrile, azoisobutyronitrile and phenixin according to 0.2: 5: 2.0: 40: 0.2: 3.0, mix the obtained CdTe quantum of 2mg step (7), mix, induced polymerization reaction 1h under 365nm ultraviolet light, obtained paper fiber surface contains quantum dot molecular imprinted polymer membrane;
(9) by parathion-methyl in ethanol/acetone eluent molecularly imprinted polymer, then successively with ethanol, distilled water wash respectively 3 times, for subsequent use;
(10) drip in paper chip by 10 μ L sample solutions, place 10 minutes, adopt distilled water to wash 3 times, detect, the detection range of linearity of parathion-methyl is 2.0 × 10
-12~ 4.3 × 10
-10mol/L, detects and is limited to 1.0 × 10
-12mol/L.
embodiment 2: the detection of metrifonate
(1) design paper chip hydrophobic wax print pattern with AdobeIllustratorCS4 on computers, be placed into by the paper cut out in wax spray printer, hydrophobic wax print pattern prints on paper;
(2) paper with wax pattern in step (1) is placed in constant temperature oven, heats 2 minutes at 80 degrees celsius;
(3) printed electrode by screen printing technique at paper base material hydrophilic region, working electrode adopts carbon slurry, contrast electrode Ag/AgCl slurry and adopts carbon slurry to electrode;
(4) batch paper chip after step (3) process is cut into single paper chip, 10 μ L gold seeds solution drop to the back side hydrophilic region being printed on working electrode, hatch 0.5h, add the 10mmol/L phosphate buffer solution that 20 μ L contain 1.2mmol/L gold chloride, 2.0mmol/L hexadecyltrimethylammonium chloride and 7.2mmol/L hydrogen peroxide, hatch 10 minutes, paper fiber surface growth gold nano grain;
(5) paper fibers gold Nanosurface fixes alkyl azide mercaptan, and 15 μ L2mmol/L nitrine undecyl mercaptan hatch 8h at paper chip electrode, and then use redistilled water washes clean, nitrogen dries up;
(6) by reacting with acrylic acid propynyl ester click chemistry, 10 μ L2mmol/L acrylic acid propynyl ester solution are added to the working electrode area that step (5) processed, and add 0.5mol/L ascorbic acid and 0.1mol/L copper sulphate mixed liquor 10 μ L, lucifuge places 10h, first use methanol wash 3 times, then second distillation water washing 3 times, dries;
(7) CdO is dissolved in octadecylene, with oleic acid Hybrid Heating to 300 DEG C, then the octadecylene being dissolved with Se powder is injected above-mentioned solution, stop reaction at 3h, reactant is injected chloroformic solution, obtain CdSe quantum dot;
(8) by metrifonate, methacrylic acid, ethylene glycol dimethacrylate, isopropyl alcohol, potassium persulfate and phenixin according to 0.5: 5: 5: 50: 0.4: 20, mix the obtained CdSe quantum dot of 2mg step (7), mix, induced polymerization reaction 1h under 365nm ultraviolet light, obtained paper fiber surface contains quantum dot molecular imprinted polymer membrane;
(9) by metrifonate in ethanol/acetone eluent molecularly imprinted polymer, then successively with ethanol, distilled water wash respectively 3 times, for subsequent use;
(10) drip in paper chip by 10 μ L sample solutions, place 10 minutes, adopt distilled water to wash 3 times, detect, the detection range of linearity of metrifonate is 2.0 × 10
-12~ 4.3 × 10
-10mol/L, detects and is limited to 1.0 × 10
-12mol/L.
Claims (5)
1. click chemistry technology prepares molecular engram paper chip sensor, it is characterized in that comprising the following steps:
(1) design paper chip hydrophobic wax bulk print pattern with AdobeIllustratorCS4 on computers, paper is cut into A4 size, is placed into by the paper cut out in wax spray printer, hydrophobic wax bulk print pattern prints on paper;
(2) paper with wax pattern in step (1) is placed in constant temperature oven, under 60-150 degree Celsius, heats 0.5-2 minute;
(3) at paper base material hydrophilic region by screen printing technique printing work electrode, contrast electrode and to electrode;
(4) batch paper chip after step (3) process is cut into single paper chip, gold seeds solution drops to the back side hydrophilic region being printed on working electrode, hatch 0.5 ~ 1h, add the phosphate buffer solution that 20 μ L contain gold chloride, hexadecyltrimethylammonium chloride and hydrogen peroxide, hatch 5 ~ 10 minutes, paper fiber surface growth gold nano grain;
(5) paper fibers gold Nanosurface fixes alkyl azide mercaptan, and 10 μ L ~ 15 μ L2mmol/L nitrine undecyl mercaptan drip hatches 8 ~ 12h in paper chip perform region, and then use redistilled water washes clean, nitrogen dries up;
(6) by reacting with acrylic acid propynyl ester click chemistry, 5 μ L ~ 10 μ L2mmol/L acrylic acid propynyl ester solution are added to the working electrode area that step (5) processed, and add 0.5mol/L ascorbic acid and 0.1mol/L copper sulphate mixed liquor 10 μ L, lucifuge places 10h, first use methanol wash, then second distillation water washing, dries;
(7) function monomer of synthesis organophosphorus insecticide molecular imprinted polymer membrane is selected;
(8) existing method is utilized to prepare semiconductor-quantum-point material;
(9) mix than by the template molecule of organophosphorus insecticide, function monomer, quantum dot, crosslinking chemical, pore-foaming agent, initiating agent and organic solvent by certain amount of substance, under 365nm ultraviolet light, induced polymerization reaction 1h, prepares paper fiber surface molecular imprinted polymer membrane;
(10) by template molecule in eluent molecular imprinted polymer membrane, then successively with ethanol, distilled water wash respectively 3 times, for subsequent use;
(11) by sample drop in paper chip, place 5 ~ 10 minutes, adopt distilled water wash 3 times, detect.
2. click chemistry technology prepares molecular engram paper chip sensor according to claim 1, it is characterized in that, paper is Whatman chromatographic paper or the ordinary filter paper of GEHealthcareWorldwide company of Chinese Shanghai Pudong, wax spray printer is Fuji-Xerox's wax spray printer, working electrode adopts carbon printing, contrast electrode Ag/AgCl prints and to electrode carbon printing, phosphate buffer solution concentration is that 10mmol/L contains 1.2mmol/L gold chloride, 2.0mmol/L hexadecyltrimethylammonium chloride and 7.2mmol/L hydrogen peroxide.
3. click chemistry technology prepares molecular engram paper chip sensor according to claim 1, it is characterized in that, semiconductor-quantum-point is CdTe quantum, CdSe quantum dot and CdS quantum dot, function monomer is Methacrylamide, acrylamide, acrylic acid, methacrylic acid, crosslinking chemical is ethylene glycol dimethacrylate, initiating agent is azoisobutyronitrile, potassium persulfate, and pore-foaming agent adopts acetonitrile, methyl alcohol, isopropyl alcohol, and organic solvent is methylene chloride or phenixin.
4. click chemistry technology prepares molecular engram paper chip sensor according to claim 1, it is characterized in that, the amount of substance ratio synthesizing the template molecule of molecular imprinting of organophosphorus pesticide residue polymer film, function monomer, crosslinking chemical, pore-foaming agent, initiating agent and organic solvent is 0.1 ~ 0.5: 5: 0.5 ~ 5: 20 ~ 55: 0.1 ~ 0.5: 1.5 ~ 30, mixes 2mg quantum dot.
5. click chemistry technology prepares molecular engram paper chip sensor according to claim 1, it is characterized in that, the ethanol/acetone of eluant, eluent to be volume ratio be 8:2.
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| CN105675597A (en) * | 2016-01-19 | 2016-06-15 | 济南大学 | Production of three-dimensional colorimetric and photoelectrochemical paper base equipment and application thereof in detection of hydrogen peroxide |
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| CN106324065A (en) * | 2016-08-18 | 2017-01-11 | 济南大学 | Preparation of chemiluminiscence light-induced electrochemical sensor and organic phosphorus pesticide detection |
| CN107024523A (en) * | 2017-04-25 | 2017-08-08 | 济南大学 | A kind of preparation and application of paper substrate optical electro-chemistry molecular engram sensor |
| CN107754614A (en) * | 2017-11-23 | 2018-03-06 | 苏州大学 | The method that hydrophobe conversion is carried out based on methacrylic acid propynyl ester perforated membrane application mercaptan alkynes click-reaction |
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| CN109142289A (en) * | 2018-07-16 | 2019-01-04 | 佛山科学技术学院 | One kind being based on CsPbBr3The detection method of perovskite quantum dot-molecular engram fluorescent optical sensor phoxim |
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| CN105924478B (en) * | 2016-05-24 | 2018-05-29 | 济南大学 | A kind of preparation method of three-dimensional paper substrate metal organic frame |
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| CN106324065B (en) * | 2016-08-18 | 2018-11-20 | 济南大学 | A kind of preparation and organophosphorus insecticide detection of the photic electrochemical sensor of chemiluminescence |
| CN108152344A (en) * | 2016-11-30 | 2018-06-12 | 香港城市大学 | Electrochemical detector |
| CN107024523A (en) * | 2017-04-25 | 2017-08-08 | 济南大学 | A kind of preparation and application of paper substrate optical electro-chemistry molecular engram sensor |
| CN107754614A (en) * | 2017-11-23 | 2018-03-06 | 苏州大学 | The method that hydrophobe conversion is carried out based on methacrylic acid propynyl ester perforated membrane application mercaptan alkynes click-reaction |
| CN107754614B (en) * | 2017-11-23 | 2020-07-24 | 苏州大学 | Method for performing hydrophilic-hydrophobic conversion by applying thiol-alkyne click reaction based on propiolic methacrylate porous membrane |
| CN109142289A (en) * | 2018-07-16 | 2019-01-04 | 佛山科学技术学院 | One kind being based on CsPbBr3The detection method of perovskite quantum dot-molecular engram fluorescent optical sensor phoxim |
| CN109142289B (en) * | 2018-07-16 | 2021-01-22 | 佛山科学技术学院 | CsPbBr-based3Detection method of phoxim of perovskite quantum dot-molecular imprinting fluorescence sensor |
| CN113533475A (en) * | 2021-07-12 | 2021-10-22 | 武汉海关技术中心 | Multi-component sulfonamide antibiotic paper-based microfluidic analysis device and analysis method |
| CN113533475B (en) * | 2021-07-12 | 2023-11-14 | 武汉海关技术中心 | Multi-component sulfonamide antibiotic paper-based microfluidic analysis device and analysis method |
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