CN108120707A - The preparation of molecular engram fluorescent sensing material and its application in high-throughput detection Rogor - Google Patents
The preparation of molecular engram fluorescent sensing material and its application in high-throughput detection Rogor Download PDFInfo
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- CN108120707A CN108120707A CN201810006486.8A CN201810006486A CN108120707A CN 108120707 A CN108120707 A CN 108120707A CN 201810006486 A CN201810006486 A CN 201810006486A CN 108120707 A CN108120707 A CN 108120707A
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- rogor
- molecular engram
- sensing material
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/64—Fluorescence; Phosphorescence
- G01N21/6428—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes"
- G01N21/643—Measuring fluorescence of fluorescent products of reactions or of fluorochrome labelled reactive substances, e.g. measuring quenching effects, using measuring "optrodes" non-biological material
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
- C08G77/08—Preparatory processes characterised by the catalysts used
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
Abstract
Preparation the present invention relates to molecular engram fluorescent sensing material and its application in high-throughput detection Rogor, it utilizes reverse microemulsion polymerization, using hydrophobicity semiconductor-quantum-point as fluorescence core, Rogor is template molecule, 3 aminopropyl triethoxysilanes are function monomer, tetraethoxysilane is crosslinking agent, the molecular engram fluorescent sensing material for being capable of specific adsorption identification Rogor is prepared using molecular imprinting technology, and the high-throughput detection of Rogor in food samples is realized to detect carrier using 96 hole elisa Plates.The present invention is of low cost, and building-up process is simple, easy control of reaction conditions, and prepared Rogor molecular engram fluorescent sensing material can be used for the absorption of Rogor to identify, the field quick detection of trace Rogor suitable for food.
Description
Technical field
The invention belongs to the detection field of organophosphorus pesticide Rogor, more particularly, to a kind of Rogor based on hydrophobicity quantum dot point
The preparation method of sub- trace fluorescent sensing material and the molecular engram fluorescent sensing material that is prepared by this method are in high pass
Application in amount detection organophosphorus pesticide Rogor.
Background technology
It is continued to develop recently as nanometer technology, the quantum dot hair swift and violent, excellent as a kind of development of advanced luminescent material
Light property is paid close attention to be subject to vast researcher, and the application in fields such as sensing detection, bio-imaging, bioprobes is wide
It is general.However, the detection for carrying out poisonous and harmful analyte using quantum point merely lacks specificity, it is impossible to which object is made choice
Property is adsorbed and realizes accurate detection.Molecular imprinting technology refers to, using a certain specific target molecule as template, prepare to the molecule
With specific selectivity high molecular polymer（Molecularly imprinted polymer）Process, molecularly imprinted polymer have prepare it is simple,
The advantages of stability is good, service life is long.Using the fluorescent characteristic that quantum dot is excellent, molecular imprinting technology is introduced, can be prepared
Go out the molecular engram fluorescent sensing material based on quantum dot light emitting, this kind of material not only can be multiple with specific recognition test substance
Quantum dot among condensation material can also provide fluorescence signal for detection, become the research hotspot of current sensor detection field.
Organophosphorus pesticide is a kind of efficient pesticides being most widely used, but it remains food-safe and health
There are larger threats.Rogor is typical organophosphorus pesticide, is absorbability organophosphor Insecticidal and acaricidal agent.Insecticidal range is wide, right
Pest and mite class have strong tag and certain stomach poison function.Viability higher omethoate can be aoxidized in insect bodies,
Mechanism of action is to inhibit the in vivo acetylcholine esterase of insect, hinders nerve conduction and causes death, has carcinogenicity, mutagenesis
Type and teratogenesis, therefore safety problem is highly valued.At present, it is mainly based upon instrument point for pesticide residue detection method
The method of analysis, such as liquid chromatography, gas chromatography, liquid chromatography-mass spectrometry, gas chromatography mass spectrometry, these methods all need
Complicated sample pretreatment process is wanted, has the shortcomings that expensive equipment, analysis time are long, complicated for operation.Further, since food is pacified
Full inspection survey has the requirements such as big, the detection efficiency requirement height of sample size, and high throughput detection has very heavy in field of detection of food safety
The meaning wanted, high-throughput detection method have very big potentiality in the multiple samples of Parallel testing, can greatly improve food
The detection flux and detection efficiency of product safety detection.Therefore, the high-throughput inspection of simple and efficient, sensitive reliable trace Rogor is developed
Survey method has very important significance.
The content of the invention
Based on above-mentioned analysis, the purpose of the present invention is：There is provided it is a kind of have to Rogor it is highly selective based on quantum dot light emitting point
Sub- trace fluorescent sensing material and its preparation method and application is established a kind of simple and efficient, sensitive reliable and is used for food samples
The molecular engram fluorescence sense system of the high-throughput detection of middle Determination of Dimethoate Residues.
The purpose of the present invention is what is be achieved through the following technical solutions：A kind of system of Rogor molecular engram fluorescent sensing material
Preparation Method, using the method for reverse microemulsion, using hydrophobicity semiconductor-quantum-point as fluorescence core, Rogor is template molecule, 3-
Aminopropyl triethoxysilane（APTES）For function monomer, tetraethoxysilane（TEOS）For crosslinking agent, ammonium hydroxide is catalyst.
The hydrophobicity semiconductor-quantum-point includes CdSe/ZnS quantum dots；
Rogor molecule has quenching effect to the fluorescence signal of prepared molecular engram fluorescent material, as determining for Rogor detection
Signal is measured, by the use of 96 hole elisa Plates as the carrier of absorption identification, realizes the high-throughput detection of Determination of Dimethoate Residues in food samples, tool
Body includes the following steps：
（1）The preparation of Rogor fluorescence molecule imprinted material presoma：By the use of hexamethylene as continuous phase, Triton X-100 and just
Hexanol is used separately as surfactant and cosurfactant.
By 7.5 mL hexamethylenes, 0.4 mL n-hexyl alcohols and 1.77 mL Triton X-100 are added in 100-mL flasks simultaneously
Stirring 20 minutes.Then 200 μ L are added under agitation（3 mg mL-1）CdSe/ZnS quantum dot solutions.After ten minutes, according to
It is secondary that 70 μ LTEOS and 100 μ L ammonium hydroxide are added in into mixture, when magnetic agitation 2 is small.
Then, add in 1 mmol and be dispersed in n-hexyl alcohol（0.2 mL）In Rogor（Template）With 30 μ L APTES（It is functional
Monomer）, flask is sealed, be kept stirring at room temperature 12 it is small when, after polymerisation, by adding in 10 into reaction system
ML acetone destroys microemulsion equilibrium system, is centrifuged, after removing supernatant, is centrifuged after being washed again with acetone
Separation, removes supernatant, obtains Rogor fluorescence molecule imprinted material presoma again.
（2）The elution of template molecule：It is methanol solution with volume ratio：Acetic acid solution=9:1, it carries out to Rogor fluorescence molecule
Imprinted material presoma carries out surname extraction to remove removing template, becomes Rogor fluorescence molecule imprinted material semi-finished product；It then will be wet
Rogor fluorescence molecule imprinted material semi-finished product be placed in vacuum drying chamber dry 3-5 it is small when, you can obtain Rogor fluorescence molecule print
Mark material.
Further, the pleasure that the Rogor molecular engram fluorescent sensing material can be in specific recognition complexity food substrate
Fruit can be applied to the identification, separation and enrichment of Rogor in complicated food substrate.
（3）Rogor detection method：
By suitable Rogor molecular engram fluorescent nano material（1mg mL-1, 100 μL）It is molten with the Rogor standard of given concentration
Liquid（5, 10, 25, 50, 100, 150 μg L−1, 100 μL）Or food samples solution is added sequentially to 96 hole elisa Plates
In.After shaking 30 minutes at room temperature, place it in multi-function microplate reader and detect its fluorescence intensity, in the excitation wave of 380nm
The fluorescence intensity of long lower measurement mixture（At 620nm）.Control experiment adds in suitable non-molecular engram fluorescence nano of Rogor
Material（1mg mL-1, 100 μL）, then the Rogor solution of addition various concentration, other steps are identical with above-mentioned experiment.
（4）The measure of Rogor content：
As more and more Rogor molecules are adsorbed by the recognition site on molecular engram fluorescent nano material, material prepared
Fluorescence signal be gradually reduced, Rogor concentration is in 5 μ g L−1 -150 μg L−1Concentration（C）In the range of with initial fluorescence and inspection
Survey the ratio of fluorescence（F 0/F）In good linear relationship（Fig. 1）：F 0/F = 0.0052 C + 1.0564 (R2 =
0.9958)；What is obtained by three times signal-to-noise ratio computation is the fluorescence sense system of probe to Rogor using the molecular engram fluorescent material
Minimum detectability（LOD）For 2.1 μ g L−1。
Compared with prior art, beneficial effects of the present invention are：
1st, Rogor molecular engram fluorescent sensing material of the present invention is a kind of and Rogor template molecule space structure and combination
The three-dimensional molecular trace hole that site matches, can specifically adsorb identification Rogor, have to object Rogor higher
Selectivity；
2nd, Rogor molecular engram fluorescent sensing material of the present invention is prepared using the method for reverse microemulsion, can be simply
Hydrophobic semiconductor-quantum-point is wrapped in molecular engram material for the detection of Rogor in hydrophilic environment, without multiple
Miscellaneous ligand exchange processes can effectively inhibit quantum dot light oxidation, improve fluorescent stability, reduce toxic heavy metal ion
Release.
3rd, the present invention molecular imprinting technology is combined with quantum dot fluorescence nanometer technology, by the use of 96 hole elisa Plates as examine
Carrier is surveyed, can realize to the quick detection of the high throughput of target molecule Rogor in complicated food substrate, there is simple, quick, spirit
The advantages that quick, high specificity, practicability are good, to China's food security, quickly detection has important practical significance.
Description of the drawings
Attached drawing is for providing a further understanding of the present invention, and a part for constitution instruction, with following specific reality
Mode is applied together for explaining the present invention, but is not construed as limiting the invention.
Fig. 1 is the scanning electron microscope (SEM) photograph for the Rogor molecular engram fluorescent sensing material that embodiment 1 is prepared.
Fig. 2 is non-molecular engram fluorescent sensing material prepared by embodiment 1（a）, molecular engram fluorescent sensing material removal
Before template Rogor molecule（c）After removing template Rogor molecule is removed（b）Fluorescence spectra.
Fig. 3 is fluorescence spectrum comparison diagram：Molecular engram fluorescent sensing material is in 50 μ g L-1Before being adsorbed in Rogor solution
（a）After absorption（b）Fluorescence spectra.
Fig. 4 is fluorescence spectrum comparison diagram：Non- molecular engram fluorescent sensing material is in 50 μ g L-1Before being adsorbed in Rogor solution
（a）After absorption（b）Fluorescence spectra.
Fig. 5 is increase of the embodiment 2 with Rogor concentration, the fluorescence spectra of Rogor molecular engram fluorescent sensing material.
Fig. 6 is the linear relationship chart of 2 molecular engram fluorescent sensing material of embodiment detection Rogor.
Fig. 7 is Rogor molecular engram fluorescent nano material prepared by embodiment 2 in 50 μ g L-1Absorption in Rogor solution
Profile of equilibrium figure.
Fig. 8 is 2 Rogor of embodiment（Dimethoate）, metrifonate（Trichlorphon）, orthene
（Acephate）And Entex（Fenthion）For molecular engram fluorescent sensing material and non-molecular engram fluorescent sensing material
'sK svValue figure.
Fig. 9 is 2 Entex of embodiment（F）, orthene（A）, metrifonate（T）And Rogor（DM）（50μgL-1）To molecule
The fluorescent quenching figure of trace fluorescent material and non-molecular engram fluorescent sensing material.
Specific embodiment
Embodiment 1
A kind of preparation method and application of the fluorescence molecule imprinted material for enriched with trace Rogor is present embodiments provided, specifically
Include the following steps：
（1）The preparation of Rogor molecular engram fluorescent sensing material presoma：By the use of hexamethylene as continuous phase, Triton X-100
Surfactant and cosurfactant are used separately as with n-hexyl alcohol.By 7.5 mL hexamethylenes, 0.4 mL n-hexyl alcohols and 1.77 mL
Triton X-100 are added in 100-mL flasks and stir 20 minutes.Then 200 μ L are added under agitation（3 mg
mL-1）CdSe/ZnS quantum dots.After ten minutes, 70 μ LTEOS and 100 μ L ammonium hydroxide, magnetic agitation 2 are added in into mixture successively
Hour.Then, add in 1 mmol and be dispersed in n-hexyl alcohol（0.2 mL）In Rogor（Template）With 30 μ L APTES（It is functional single
Body）, be sealed against, be kept stirring at room temperature 12 it is small when, after polymerisation, by adding in 10 mL third into reaction system
Ketone destroys microemulsion equilibrium system, is centrifuged, and after removing supernatant, is centrifuged again after acetone washing, then
It is secondary to remove supernatant, obtain the predecessor of Rogor fluorescence molecule imprinted material.
（2）The elution of template molecule：With methanol/acetic acid solution（9:1,v/v）It carries out to Rogor fluorescence molecule imprinted material
Predecessor carry out surname extraction to remove removing template, then place it in vacuum drying chamber dry 3-5 it is small when, you can found pleasure in
Fruit fluorescence molecule imprinted material.
Comparative example 1
This comparative example provides a kind of preparation method of the non-molecular engram material of fluorescence, is as follows：
1）The preparation of the non-molecular engram material presoma of fluorescence：Reverse Microemulsion System used in during being somebody's turn to do, function monomer,
The dosage of crosslinking agent, catalyst, separation, the process of purifying and the preparation of Rogor molecular engram fluorescent sensing material in embodiment 1
It is identical, simply without adding in template molecule Rogor during preparation；
2）The preparation of the non-molecular engram material of fluorescence：By non-fluorescence trace nano material presoma methanol/second of above-mentioned preparation
Acid solution（9:1,v/v）Carry out surname extraction, and place it in vacuum drying chamber dry 3-5 it is small when, obtain non-molecular engram
Fluorescent material.
Embodiment 2
（1）The time of equilibrium adsorption of Rogor molecular engram fluorescent sensing material
Rogor molecular engram fluorescent sensing material described in embodiment 1 is scattered in configuration Rogor molecular engram fluorescence in ultra-pure water
Nano material dispersion liquid（1mg mL-1）, 100 μ L dispersion liquids are added in 96 hole elisa Plates, add in 100 μ L（50 μg L−1）
The aqueous solution of Rogor shakes 1,3,5,7,10,15,20,30,35,40,45,50 minutes, places it in more work(respectively at room temperature
Its fluorescence intensity can be detected in microplate reader, the fluorescence intensity of mixture is measured under the excitation wavelength of 380nm（At 620nm）.
Experimental result is as shown in fig. 7, prepared Rogor molecular engram fluorescent sensing material has object faster absorption power
Performance is learned, when adsorption time is 30 minutes, has reached adsorption equilibrium.Compared with traditional molecular engram fluorescent nano material,
The Rogor molecular engram fluorescent sensing material has quick adsorption dynamics adsorption kinetics, can greatly improve detection efficiency.
（2）The selectivity of Rogor molecular engram fluorescent sensing material
The selectivity and antijamming capability, selection and its molecule adsorb to evaluate prepared molecular engram fluorescent material to Rogor
Structure is similar and may common existing organophosphorus pesticide metrifonate（Trichlorphon）, orthene（Acephate）、
Entex（Fenthion）As competitor, the experiment of making choice property.Specific experiment method includes：100 μ L Rogor molecules are printed
Mark fluorescent sensing material（1 mg mL-1）It adds in 96 hole elisa Plates, adds in the Rogor of 100 μ L（Dimethoate）And metrifonate
（Trichlorphon）, orthene（Acephate）, Entex（Fenthion）Aqueous solution（50 μg L-1）, at room temperature
Concussion 30 minutes, places it in multi-function microplate reader and detects its fluorescence intensity, and excitation wavelength is 380 nm, and launch wavelength is
620 nm.Control experiment needs to add in the 100 non-molecular engram fluorescent materials of μ L Rogor（1mg mL-1）, then add in 100 μ L's
Rogor（Dimethoate）And metrifonate（Trichlorphon）, orthene（Acephate）, Entex（Fenthion）
Aqueous solution（50 μg L-1）.Evaluation index isK sv,K svFor the fluorescent quenching constant in Stern-Volmer equations.
Experimental result is as shown in figure 8, the fluorescence imprinted material prepared by embodiment 1 has Rogor preferable absorption to imitate
Fruit, to other equal unobvious of competitor adsorption effect of Rogor, this is primarily due to the three-dimensional knowledge constructed by molecular engram material
Other hole, can be with specific adsorption object Rogor, and therefore, prepared molecular engram fluorescent material is to the adsorption capacity of Rogor
Much surmount other molecules.As control experiment non-fluorescence trace nano material for Rogor and competitor adsorption capacity compared with
Weak, reason is that the identification hole of specificity is not formed in the preparation process of non-molecular engram fluorescent material, therefore selects to know
The ability of other molecule is poor.The antijamming capability of prepared molecular engram fluorescent material is by measuring molecular engram fluorescent material
Pair with a certain concentration Rogor（50 μg L-1）With other structures analog（50 μg L-1）Fluorescence response under concurrent conditions come into
Row, experimental result is as shown in figure 9, the fluorescence intensity of prepared molecular engram fluorescent material exists in Rogor and analogue
Under conditions of with only Rogor exist be to compare no significant variation, experimental result these types analogue coexists hardly
Disturb the detection of Rogor（Rogor（DM）, metrifonate（T）, orthene（A）, Entex（F））.By fluorescence imprinted material with
Non-fluorescence trace nano material shows the pleasure prepared by embodiment 1 for the selective absorption of Rogor and antijamming capability experiment
Fruit molecular engram fluorescent sensing material has good selectivity absorption property, which can be applied to complicated food samples
Enrichment, separation and the detection of Rogor in matrix.
Claims (7)
1. a kind of preparation method of Rogor molecular engram fluorescent sensing material, it is characterised in that：Prepare the Rogor molecular engram
The method that fluorescent sensing material uses reverse microemulsion, using hydrophobicity semiconductor-quantum-point as fluorescence core, Rogor is template point
Son, 3- aminopropyl triethoxysilanes are function monomer, and tetraethoxysilane is crosslinking agent, and ammonium hydroxide is catalyst.
2. a kind of preparation method of Rogor molecular engram fluorescent sensing material according to claim 1, it is characterised in that：Institute
Stating hydrophobicity semiconductor-quantum-point includes CdSe/ZnS quantum dots.
3. a kind of preparation method of Rogor molecular engram fluorescent sensing material according to claim 1, it is characterised in that：Bag
Include following steps：
（1）The preparation of Rogor molecular engram fluorescent sensing material presoma：By the use of hexamethylene as continuous phase, Triton X-100
It is cosurfactant as surfactant and n-hexyl alcohol；
By 7.5 mL hexamethylenes, 0.4 mL n-hexyl alcohols and 1.77 mL Triton X-100 are added in 100-mL flasks and stir
20 minutes, it was 3 mg mL then to add in concentration under agitation-1200 μ L of CdSe/ZnS quantum dot solutions；After ten minutes,
70 μ L TEOS and 100 μ L ammonium hydroxide are added in into mixture successively, when magnetic agitation 2 is small；Then, 1 mmol is added in be dissolved in
Rogor in n-hexane, volume are 0.2 mL, add 30 μ L APTES, flask is sealed, is kept stirring 12 at room temperature
Hour, after polymerisation, 10 mL acetone are added in into reaction system for destroying microemulsion equilibrium system, carry out centrifugation point
From after removing supernatant, being centrifuged after being washed again with acetone, remove supernatant again, obtain Rogor molecular engram
Fluorescent sensing material presoma；
（2）The elution of template molecule：It is methanol with volume ratio by Rogor molecular engram fluorescent sensing material presoma：Acetic acid=9:
1 solution carry out surname extraction go template be placed in vacuum drying chamber dry 3-5 it is small when to get to Rogor fluorescence molecule trace
Fluorescent sensing material.
4. a kind of preparation method of Rogor molecular engram fluorescent sensing material according to claim 1 or 2 or 3, feature
It is：Rogor molecular engram fluorescent sensing material is applied in food in the high-throughput detection of trace Rogor.
5. the preparation method of a kind of Rogor molecular engram fluorescent sensing material according to claim 4, it is characterised in that happy
The application process of the high-throughput detection of fruit molecular engram fluorescent sensing material trace Rogor in food is：It is 1 by 100 μ L concentration
mg mL-1Rogor molecular engram fluorescent sensing material aqueous dispersions and Rogor standard solution be added sequentially to 96 hole elisa Plates
In, it shakes 30 minutes at room temperature, 96 hole elisa Plates is placed in fluorescence intensity in multi-function microplate reader, in swashing for 380 nm
The fluorescence intensity of mixture is measured under the conditions of the launch wavelength of hair wavelength and 620 nm, realizes the high throughput assay of a large amount of samples.
6. a kind of preparation method of Rogor molecular engram fluorescent sensing material according to claim 5, it is characterised in that：
In food in the application of the high-throughput detection of trace Rogor, the fluorescence sense body of Rogor molecular engram fluorescent sensing material structure is utilized
It is 5 μ g L for the linear detection range of Rogor detection to be−1 -150 μg L−1。
7. a kind of preparation method of Rogor molecular engram fluorescent sensing material according to claim 6, it is characterised in that：It is happy
The linearity test minimum detectability of fruit is 2.1 μ g L−1。
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| CN108827922A (en) * | 2018-06-13 | 2018-11-16 | 中国农业科学院农业质量标准与检测技术研究所 | Pesticide residue based on multiple bionical identification visualizes Fast Detection Technique |
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| CN109142290A (en) * | 2018-07-16 | 2019-01-04 | 佛山科学技术学院 | For detecting the CsPbBr of phoxim3Perovskite quantum dot-molecular engram fluorescent optical sensor and preparation method thereof |
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| CN110018142A (en) * | 2019-03-20 | 2019-07-16 | 西南交通大学 | Composite fluorescence substrate, the preparation method and application of composite fluorescence substrate |
| CN110018142B (en) * | 2019-03-20 | 2021-10-22 | 西南交通大学 | Composite fluorescent substrate, preparation method and application thereof |
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