CN102977403A - Molecularly imprinted membrane based on porphyrin and acrylic monomers for organophosphorus pesticide and application thereof - Google Patents
Molecularly imprinted membrane based on porphyrin and acrylic monomers for organophosphorus pesticide and application thereof Download PDFInfo
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- CN102977403A CN102977403A CN2012105632526A CN201210563252A CN102977403A CN 102977403 A CN102977403 A CN 102977403A CN 2012105632526 A CN2012105632526 A CN 2012105632526A CN 201210563252 A CN201210563252 A CN 201210563252A CN 102977403 A CN102977403 A CN 102977403A
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- 0 Oc1ccc(C(C(*2*3(C4C5=CC=C44)*6=C7C=CC6=C5c5ccccc5)C=CC2=C7c2ccccc2)C(C=C2)=*3C2=C4c2ccccc2)cc1 Chemical compound Oc1ccc(C(C(*2*3(C4C5=CC=C44)*6=C7C=CC6=C5c5ccccc5)C=CC2=C7c2ccccc2)C(C=C2)=*3C2=C4c2ccccc2)cc1 0.000 description 1
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Abstract
The invention discloses a molecularly imprinted membrane for rapid detection of an organophosphorus pesticide and application thereof. The molecularly imprinted membrane is prepared by taking the organophosphorus pesticide as a template molecule as well as metalloporphyrin and acrylic monomers as functional monomers. The molecularly imprinted membrane provided by the invention is simple in preparation method. A three-dimensional cavity formed in the molecularly imprinted membrane has exclusive distinctiveness and can only be combined with a template molecule in a special structure, therefore, the molecularly imprinted membrane provided by the invention has higher selectivity to corresponding template molecules, and can be used for rapid detection of the organophosphorus pesticide.
Description
Technical field
The invention belongs to the sensing material and the preparation method that detect organophosphorus pesticide, specifically relate to a kind of organophosphorus pesticide molecular engram film and application thereof based on porphyrin and acrylic monomer.
Background technology
Dimethyl methyl phosphonate is a kind of organophosphorus pesticide analogue, and it has, the characteristics such as toxicity little, operational safety similar to the organophosphorus pesticide molecular structure.Organophosphorus pesticide is one of primary categories of current agricultural chemicals, and it has almost spreaded all over all areas of agricultural chemicals.The organophosphorus pesticide commodity of using in the world at present still reach hundreds of, and aspect sterilant, organophosphorus insecticide has very important status especially.It has also produced widely side effect when bringing increases in grain production and enormous benefits.The daily edible fruit of people, what have in the vegetables has the residual of organophosphorus pesticide, and these remainss of pesticide can be accumulated in people's body, cause easily cancer, the pathologies such as deformity.At present organophosphorus pesticide has become a stable problem of harm people's daily life, therefore realizes a kind of simple to its microscratch amount, and economy detects fast, and the monitoring that food safety is carried out constantly is significant.
The detection pesticide residue mainly contain vapor-phase chromatography (GC), liquid phase chromatography (HPLC), gas chromatography mass spectrometry method (GC-MS), LC-MS (HPLC-MS), capillary electrophoresis and mass spectrum and are used in conjunction (CE-MS), multi-stage ms coupling etc. at present.But the instrument that detects is expensive, large-scale, and the determination process is loaded down with trivial details, need the professional to operate and detect the shortcoming such as many consuming time also so that this technology can only be used for the feeler mechanism of laboratory and specialty and can not well be popularized.
Summary of the invention
The preparation method and the detection method that the purpose of this invention is to provide a kind of dimethyl methyl phosphonate molecular engram film, it prepares molecular engram film by in-situ polymerization on sheet glass, the film that this method makes out by selecting specific function monomer, it is quick so that the detection in later stage is easy.
The object of the present invention is achieved like this:
One aspect of the present invention relates to a kind of molecular engram film for detection of organic phosphorus pesticide, it is characterized in that the preparation method of described molecular engram film comprises the steps:
(1) organophosphorus pesticide template molecule, function monomer A and function monomer B are dissolved in the pore-creating agent, mix vibration, place refrigerator overnight, obtain microsphere-function monomer mixture, wherein
The organophosphorus pesticide template molecule, function monomer A, the mol ratio of function monomer B is 1: 3～6: 0.1～2
Described function monomer A is a kind of in methacrylic acid MAA, vinylformic acid (AA), trifluoromethyl acrylate (TFMAA), the methacrylic ester (MMA), is preferably methacrylic acid;
Described function monomer B is derivatives of porphyrin, and described derivatives of porphyrin is selected from 5-(4-methacryloxypropyl phenyl)-10,15,20-triphenyl zinc protoporphyrin and other corresponding metalloporphyrins, (shown in the structural formula 1, M is selected from metallic zinc, gadolinium, cobalt, manganese, iron, copper, nickel).5-10,15,20-four-(4-methacryloxypropyl phenyl)-phenyl zinc protoporphyrin and other corresponding metalloporphyrins (zinc, gadolinium, cobalt, manganese, iron, copper, nickel).
Formula 1
Pore-creating agent is chloroform and/or methylene dichloride;
(2) pre-treatment of sheet glass
The activation of slide:
First slide is scrubbed to remove surperficial dirt with washing powder, sulfuric acid lotion successively, after making the water flushing slide is immersed in the acetone soln, then sonic oscillation, repeat to clean with industrial spirit again, in NaOH (1M) solution, soak 30min, successively with hydrochloric acid and water flushing, dry up at last stand-by with nitrogen subsequently;
The silanization of slide: will wash with toluene through the slide of overactivation, the implantation quality mark is 8～12% the 3-methacryloxypropyl trimethoxy silane (toluene solution of γ-MPS) subsequently, behind room temperature reaction 1～3h, again wash with toluene, to remove remaining γ-MPS, at last slide glass is dried up for subsequent use;
(3) preparation of molecular engram film
Linking agent added in the solution in (1), and adding initiator, logical nitrogen mixes vibration, cooling, with microsyringe with injection of solution to sheet glass, and make its even distribution, press a clean sheet glass in the above, and vacuumize, to remove air in the solution, the ultra violet lamp initiation reaction of usefulness 365nm 10～24 hours; After having reacted, the separate glass plate obtains molecular engram film.
(4) removal of imprinted templates molecule
With the template molecule above the elutriant wash-out film, dry stand-byly, wherein elutriant is that volume ratio is 8～10: 1 methyl alcohol/acetic acid mixing solutions.
In a preferred embodiment of the present invention, described template molecule is selected from dimethyl methyl phosphonate, phorate, Rogor.
In a preferred embodiment of the present invention, described linking agent is selected from ethylene glycol dimethacrylate (EGDMA), trimethylolpropane trimethacrylate (TRIM), divinylbenzene (DVB) or N, N '-methylene-bisacrylamide;
In a preferred embodiment of the present invention, initiator is that Diisopropyl azodicarboxylate (AIBN), 2,2'-Azobis(2,4-dimethylvaleronitrile) or benzoyl peroxide (BPO) initiator are selected from Diisopropyl azodicarboxylate.
The present invention also relates to the application of above-mentioned molecular engram film in detection of organic phosphorus pesticide on the other hand, described application comprises the steps: to use above-mentioned molecular engram film and corresponding organophosphorus pesticide to react, then by the spectrum change of fluorescence (ultraviolet) photometer detection molecules blotting membrane before and after reaction, preferably, described organophosphorus pesticide has the chemical structure identical or similar with template molecule.
Preferably, detection of organic phosphorus pesticide of the present invention comprises the steps: to prepare the organophosphorus pesticide standardized solution of a series of microscratch amounts, the film that strips is put into reference liquid carry out absorption reaction, reacted film is carried out spectroscopic analysis, described spectrum is preferably fluorescence spectrum; And set up the one by one contrast relationship of spectrum and reference liquid, the characteristics of this method are to use sheet glass to replace cuvette, and film can Reusability, have set up the abosrption spectrogram of the organophosphorus pesticide molecule of microscratch amount.
Description of drawings
Fig. 1: the scanning electron microscope (left figure is before wash-out, after right figure is wash-out) take metalloporphyrin zinc and MAA as the molecular engram film of the dimethyl methyl phosphonate of function monomer;
Fig. 2: the fluorescence spectrum before and after the masterplate molecule wash-out take metalloporphyrin zinc and MAA as the molecular engram film of the dimethyl methyl phosphonate of function monomer changes (absorbancy of B before the wash-out, C is the absorbancy behind the wash-out);
Fig. 3: film and series concentration (10
-2-10
-7Mol.L
-1) (the B-G curve is respectively corresponding concentration 10 to DMMP reaction fluorescence pattern
-2-10
-7Mol.L
-1The time absorbancy).
Embodiment
The invention will be further described below in conjunction with embodiment:
The preparation of embodiment 1:DMMP molecular engram film
(1) get dimethyl methyl phosphonate (DMMP) 1mmol, methacrylic acid (MAA) 3mmol, and zinc protoporphyrin (shown in the structural formula 1) 1mmol are dissolved in the 10ml chloroformic solution, mix vibration, are put in the refrigerator hold over night.
(2) in the solution in linking agent ethylene glycol dimethacrylate (EGDMA) adding (1), and add initiator (AIBN), logical nitrogen mixes vibration 30mins, cools off.With microsyringe with injection of solution to sheet glass, and make its even distribution, press a clean sheet glass in the above, and vacuumize, to remove air in the solution.Under 25 ℃, with 365nm ultra violet lamp initiation reaction 10～24 hours.After having reacted, the separate glass plate obtains molecular engram film, and resulting polymers is washed till without microsphere with methyl alcohol/acetic acid 9/1 (V/V).Design sketch such as Fig. 1 before and after the gained molecular imprinting membrane elution.
DMMP detects: get 216.7 μ L DMMP sterlings, in the 20mL volumetric flask, configuration concentration is 1x10 with the methylene dichloride constant volume
-1Mol.L
-1The DMMP mother liquor, from mother liquor, measure again an amount of solution, with methylene dichloride configuration different concns DMMP solution, concentration range is 10
-2-10
-7Mol.L
-1Treat that solution mixes, after stablizing.With molecular engram film add respectively carry out absorption reaction in the different concns DMMP solution after, survey its spectrum change, gained spectrum change such as Fig. 3.
Embodiment 2: the preparation of Rogor molecular engram film
(1) the fruit 1mmol that seeks pleasure, methacrylic acid (MAA) 3mmol, and gadolinium porphyrin 1mmol are dissolved in the 10ml chloroformic solution, mix vibration, are put in the refrigerator hold over night.
(2) in the solution in linking agent ethylene glycol dimethacrylate (EGDMA) adding (1), and add initiator (AIBN), logical nitrogen mixes vibration 30mins, cools off.With microsyringe with injection of solution to sheet glass, and make its even distribution, press a clean sheet glass in the above, and vacuumize, to remove air in the solution.Under 30 ℃, with 365nm ultra violet lamp initiation reaction 10～24 hours.After having reacted, the separate glass plate obtains molecular engram film, and resulting polymers is washed till without microsphere with methyl alcohol/acetic acid 9/1 (V/V).
DMMP detects: get 216.7 μ L DMMP sterlings, in the 20mL volumetric flask, configuration concentration is 1x10 with the methylene dichloride constant volume
-1Mol.L
-1The DMMP mother liquor, from mother liquor, measure again an amount of solution, with methylene dichloride configuration different concns DMMP solution, concentration range is 10
-3-10
-7, 5x 10
-8Mol.L
-1Treat that solution mixes, after stablizing.With molecular engram film add respectively carry out absorption reaction in the different concns DMMP solution after, survey its spectrum change.
Embodiment 3: the preparation of phorate molecular engram film
(1) get phorate 1mmol, methacrylic acid (MAA) 3mmol, and cobalt porphyrin 0.5mmol are dissolved in the 7.5ml chloroformic solution, mix vibration, are put in the refrigerator hold over night.
(2) in the solution in linking agent ethylene glycol dimethacrylate (EGDMA) adding (1), and add initiator (AIBN), logical nitrogen mixes vibration 30mins, cools off.With microsyringe with injection of solution to sheet glass, and make its even distribution, press a clean sheet glass in the above, and vacuumize, to remove air in the solution.Under 25 ℃, with 365nm ultra violet lamp initiation reaction 10～24 hours.After having reacted, the separate glass plate obtains molecular engram film, and resulting polymers is washed till without microsphere with methyl alcohol/acetic acid 9/1 (V/V).
DMMP detects: get 216.7 μ L DMMP sterlings, in the 20mL volumetric flask, configuration concentration is 1x10 with the methylene dichloride constant volume
-1Mol.L
-1The DMMP mother liquor, from mother liquor, measure again an amount of solution, with methylene dichloride configuration different concns DMMP solution, concentration range is 10
-410
-7, 1x10
-8, 5x10
-8Mol.L
-1Treat that solution mixes, after stablizing.With molecular engram film add respectively carry out absorption reaction in the different concns DMMP solution after, survey its spectrum change.
Embodiment 4: the preparation of isocarbophos molecular engram film
(1) get isocarbophos 1mmol, methacrylic acid (MAA) 3mmol, and manganoporphyrin 0.5mmol are dissolved in the 7.5ml chloroformic solution, mix vibration, are put in the refrigerator hold over night.
(2) in the solution in linking agent ethylene glycol dimethacrylate (EGDMA) adding (1), and add initiator (AIBN), logical nitrogen mixes vibration 30mins, cools off.With microsyringe with injection of solution to sheet glass, and make its even distribution, press a clean sheet glass in the above, and vacuumize, to remove air in the solution.Under 30 ℃, with 365nm ultra violet lamp initiation reaction 10～24 hours.After having reacted, the separate glass plate obtains molecular engram film, and resulting polymers is washed till without microsphere with methyl alcohol/acetic acid 9/1 (V/V).
DMMP detects: get 216.7 μ L DMMP sterlings, in the 20mL volumetric flask, configuration concentration is 1x10 with the methylene dichloride constant volume
-1Mol.L
-1The DMMP mother liquor, from mother liquor, measure again an amount of solution, with methylene dichloride configuration different concns DMMP solution, concentration range is 10
-5-10
-7, 1x10
-8, 5x10
-8, 5x10
-9Mol.L
-1Treat that solution mixes, after stablizing.With molecular engram film add respectively carry out absorption reaction in the different concns DMMP solution after, survey its spectrum change.
Result of implementation is
Can find out that such as Fig. 1 the molecular engram film before the wash-out has formed good polymkeric substance, occur a lot of holes behind the wash-out, prove that blotting membrane successfully synthesizes; The fluorescence pattern of Fig. 2 is that fluorescence spectrum changes before and after the blotting membrane wash-out, can find out that wash-out front and back fluorescence intensity obviously dies down, and produce faint blue shift; Fig. 3 is the fluorescence pattern of blotting membrane and series concentration DMMP solution reaction, can find out that fluorescence intensity is different under the different concns, and along with concentration reduces, fluorescence intensity weakens, and illustrates that the prepared molecular engram film of the present invention can effectively be applied to the microscratch amount detection of organophosphorus pesticide molecule.
The above be the specific embodiment of the present invention only, but protection scope of the present invention is not limited to this, and any variation or replacement of expecting without creative work all should be encompassed within protection scope of the present invention.Therefore, protection scope of the present invention should be as the criterion with the protection domain that claims were limited.
Claims (6)
1. a molecular engram film that is used for detection of organic phosphorus pesticide is characterized in that the preparation method of described molecular engram film comprises the steps:
(1) organophosphorus pesticide template molecule, function monomer A and function monomer B are dissolved in the pore-creating agent, mix vibration, place refrigerator overnight, obtain microsphere-function monomer mixture, wherein
The organophosphorus pesticide template molecule, function monomer A, the mol ratio of function monomer B is 1: 3～6: 0.1～2
Described function monomer A is a kind of in methacrylic acid (MAA), vinylformic acid (AA), trifluoromethyl acrylate (TFMAA), the methacrylic ester (MMA), is preferably methacrylic acid;
Described function monomer B is derivatives of porphyrin, described derivatives of porphyrin is selected from 5-(4-methacryloxypropyl phenyl)-10,15,20-triphenyl gadolinium porphyrin, 5-(4-methacryloxypropyl phenyl)-10,15,20-triphenyl zinc protoporphyrin, 5-(4-methacryloxypropyl phenyl)-10,15,20-triphenyl cobalt porphyrin, 5-(4-methacryloxypropyl phenyl)-10,15,20-triphenyl manganoporphyrin, 5-(4-methacryloxypropyl phenyl)-10,15,20-triphenyl iron porphyrin, 5-(4-methacryloxypropyl phenyl)-10,15,20-triphenyl copper porphyrin, 5-(4-methacryloxypropyl phenyl)-10,15, one or more in the 20-triphenyl nickel-porphyrin;
Pore-creating agent is chloroform and/or methylene dichloride;
(2) pre-treatment of sheet glass
The activation of slide: first slide is scrubbed to remove surperficial dirt with washing powder, sulfuric acid lotion successively, be immersed in the acetone soln after making the water flushing, then sonic oscillation, repeat to clean with industrial spirit again, in NaOH solution, soak more than the 20min, successively with hydrochloric acid and water flushing, dry up at last stand-by with nitrogen subsequently;
The silanization of slide: will wash with toluene through the slide of overactivation, put into subsequently massfraction and be 8～12% the 3-methacryloxypropyl trimethoxy silane (toluene solution of γ-MPS), behind room temperature reaction 1～3h, again wash with toluene, to remove remaining γ-MPS, at last slide glass is dried up for subsequent use;
(3) preparation of molecular engram film
Linking agent added in the solution in (1), and adding initiator, logical nitrogen mixes vibration, cooling, with microsyringe with injection of solution to sheet glass, and make its even distribution, press a clean sheet glass in the above, and vacuumize, to remove air in the solution, the ultra violet lamp initiation reaction of usefulness 365nm 10～24 hours; After having reacted, the separate glass plate obtains molecular engram film.
(4) removal of imprinted templates molecule
With the template molecule above the elutriant wash-out film, dry stand-byly, wherein elutriant is that volume ratio is 8～10: 1 methyl alcohol/acetic acid mixing solutions.
2. molecular engram film according to claim 1, described template molecule is selected from dimethyl methyl phosphonate, phorate, Rogor, isocarbophos.
3. molecular engram film according to claim 2, described linking agent is selected from ethylene glycol dimethacrylate (EGDMA), trimethylolpropane trimethacrylate (TRIM), divinylbenzene (DVB) or N, N '-methylene-bisacrylamide.
4. molecular engram film according to claim 3, initiator is that Diisopropyl azodicarboxylate (AIBN), 2,2'-Azobis(2,4-dimethylvaleronitrile) or benzoyl peroxide (BPO) initiator are selected from Diisopropyl azodicarboxylate.
5. the application of the described molecular engram film of claim 1-4 any one in detection of organic phosphorus pesticide, preferred, the concentration of described organophosphorus pesticide is between 10
-2-10
-7Between the mol/L, further preferably between 10
-4～10
-7Between the mol/L.
6. application according to claim 5, described application comprises the steps: to use above-mentioned molecular engram film to adsorb corresponding organophosphorus pesticide, then detect the content of organophosphorus pesticide by fluorescence and/or ultraviolet photometer, preferably, described organophosphorus pesticide has the chemical structure identical or similar with template molecule.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103724655A (en) * | 2013-12-18 | 2014-04-16 | 陕西科技大学 | Method for preparing epothilone molecularly imprinted polymer film by adopting mixed template |
| US20140162148A1 (en) * | 2012-12-07 | 2014-06-12 | Samsung Electronics Co., Ltd. | Polymeric compound, oxygen permeable membrane, and electrochemical device |
| CN104190467A (en) * | 2014-07-23 | 2014-12-10 | 江苏大学 | Preparation method of intelligent non-PNIPAm-based temperature-sensitive nickel catalyst |
| CN104330552A (en) * | 2014-11-20 | 2015-02-04 | 山东农业大学 | Method for detecting dipterex and acephate by virtue of enzyme labelled bionic immunoassay |
| CN105572349A (en) * | 2016-01-14 | 2016-05-11 | 江苏大学 | Preparation of pesticide-carbaryl molecular-imprinting bionic rapid-detection test strip and application thereof |
| CN106279534A (en) * | 2016-08-10 | 2017-01-04 | 南昌航空大学 | A kind of oxygen metal anion imprinted polymer and preparation method thereof |
| CN112858285A (en) * | 2021-02-04 | 2021-05-28 | 中南民族大学 | Method for visually detecting organochlorine pesticide |
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Cited By (11)
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| US20140162148A1 (en) * | 2012-12-07 | 2014-06-12 | Samsung Electronics Co., Ltd. | Polymeric compound, oxygen permeable membrane, and electrochemical device |
| US9276301B2 (en) * | 2012-12-07 | 2016-03-01 | Samsung Electronics Co., Ltd. | Polymeric compound, oxygen permeable membrane, and electrochemical device |
| CN103724655A (en) * | 2013-12-18 | 2014-04-16 | 陕西科技大学 | Method for preparing epothilone molecularly imprinted polymer film by adopting mixed template |
| CN103724655B (en) * | 2013-12-18 | 2015-11-25 | 陕西科技大学 | A kind of method adopting hybrid template to prepare ebormycine molecular imprinted polymer membrane |
| CN104190467A (en) * | 2014-07-23 | 2014-12-10 | 江苏大学 | Preparation method of intelligent non-PNIPAm-based temperature-sensitive nickel catalyst |
| CN104190467B (en) * | 2014-07-23 | 2016-07-06 | 江苏大学 | A kind of preparation method of non-PNIPAm base temperature sensitive intelligence Raney nickel |
| CN104330552A (en) * | 2014-11-20 | 2015-02-04 | 山东农业大学 | Method for detecting dipterex and acephate by virtue of enzyme labelled bionic immunoassay |
| CN105572349A (en) * | 2016-01-14 | 2016-05-11 | 江苏大学 | Preparation of pesticide-carbaryl molecular-imprinting bionic rapid-detection test strip and application thereof |
| CN106279534A (en) * | 2016-08-10 | 2017-01-04 | 南昌航空大学 | A kind of oxygen metal anion imprinted polymer and preparation method thereof |
| CN112858285A (en) * | 2021-02-04 | 2021-05-28 | 中南民族大学 | Method for visually detecting organochlorine pesticide |
| CN112858285B (en) * | 2021-02-04 | 2022-04-29 | 中南民族大学 | Method for visually detecting organochlorine pesticide |
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Application publication date: 20130320 |