CN104017126A - Tocopherol molecularly imprinted fluorescent polymer and preparation method and application thereof - Google Patents
Tocopherol molecularly imprinted fluorescent polymer and preparation method and application thereof Download PDFInfo
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- CN104017126A CN104017126A CN201410277432.7A CN201410277432A CN104017126A CN 104017126 A CN104017126 A CN 104017126A CN 201410277432 A CN201410277432 A CN 201410277432A CN 104017126 A CN104017126 A CN 104017126A
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- tocopherol
- fluorescent polymer
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Abstract
The invention relates to a preparation method of a tocopherol molecularly imprinted fluorescent polymer. The method comprises the following steps: by taking tocopherol as a template molecule, adding quantum dot fluorescent nanomaterials; carrying out thermal polymerization reaction to obtain the fluorescent polymer by adopting a functional monomer capable of forming a hydrogen bond together with the template molecule under the existence of a cross-linking agent and an initiator, and then removing tocopherol in the polymer so as to obtain the tocopherol molecularly imprinted fluorescent polymer. The tocopherol molecularly imprinted fluorescent polymer prepared by adopting the method has the advantages of being regular in shape, high in mechanical strength, good in selective adsorption effect, good in physical and chemical properties and the like, can be applied to separation, purification and enrichment of tocopherol from complex food substrates such as grease, rice and the like, and has a broad application prospect.
Description
Technical field
The present invention relates to molecularly imprinted polymer technical field, relate in particular to a kind of tocopherol molecular imprinting fluorescent polymer and methods for making and using same thereof.
Background technology
Tocopherol, has another name called vitamin-E, is the derivative of Dihydrobenzofuranes-6-alcohol, belongs to a kind of liposoluble vitamin, has that biological activity is high, safe, the easy feature such as be absorbed by the body concurrently.Pure tocopherol is tasteless thick weak yellow liquid, is soluble in organic solvent and the greases such as ethanol, ether, acetone, benzene, chloroform, water insoluble.Its fusing point is 2.5-3.5 DEG C, and density (25 DEG C) is 0.95g/cm
3, under molecular distillation condition 66.7pa, boiling point is 200-220 DEG C.Tocopherol is more stable to heat, even be not still damaged under 200 DEG C of high temperature.Natural tocopherol has oxidation resistant effect, and it not only has the effect of interrupting oxidation radical, and can singlet-oxygen quenching.Tocopherol is one of now widely used antioxidant.
Molecular imprinting is that nearly one growing up for 20 years has to certain specific molecule (masterplate molecule) technology that specificity is selected, and is regarded as the affine technology of a kind of novel specificity.The polymkeric substance of preparing by this technology is called as molecularly imprinted polymer.Because molecularly imprinted polymer can specific binding template molecule, preparation method is simple, can Reusability, and physical strength is higher, stability is better, and molecularly imprinted polymer had been widely used in the material of chromatographic column, Solid-Phase Extraction, membrane extraction, artificial antibody and sensor in the last few years.
Quantum dot is a kind of three-dimensional cluster, and it forms size in nanometer scale by a limited number of atom.The physical behavior of this three-dimensional system is as similar to atom in optical, electrical character, thereby is known as " artificial atom ".Quantum dot is generally spherical or class is spherical, and particle diameter is 1～10nm, and it is at the atom of nanoscale and molecular aggregate.Quantum dot fluorescence material is the class nano material being widely studied in recent years, due to its unique photoluminescence property, (light stability is better, fluorescence lifetime is longer, fluorescent emission wavelength Modulatory character, quantum yield is higher), higher susceptibility, larger specific surface area, makes them in the fields such as biomarker, biological detection and bio-imaging, bring into play more and more important effect as fluorescent probe.
Therefore, be desirable to provide a kind of tocopherol molecular imprinting fluorescent polymer, traditional molecular imprinting is combined with novel quantum dot fluorescence nano material, thereby realize the Fast Detection Technique to target molecule-tocopherol, there is the advantages such as quick, simple, practical.
Summary of the invention
It is simple that the problem to be solved in the present invention is to provide a kind of preparation process, and the product physical strength of preparation is high, good physical and chemical properties, tocopherol molecular imprinting fluorescent polymer that selective adsorption capacity is strong and its production and use.
For solving the problems of the technologies described above, the technical solution used in the present invention is: a kind of tocopherol molecular imprinting fluorescent polymer, taking tocopherol as template molecule, add quantum dot fluorescent nano material, employing can form with masterplate molecule the function monomer of hydrogen bond, under linking agent and initiator existence, carry out heat polymerization preparation.
Preferably, described function monomer is methacrylic acid; Described tocopherol is alpha-tocopherol; Described quantum dot fluorescence nano material is CdSe/ZnS quantum dot.
Preferably, described linking agent is Ethylene glycol dimethacrylate; Described initiator is Diisopropyl azodicarboxylate.
The present invention also provides a kind of method of preparing tocopherol molecular imprinting fluorescent polymer as above, comprises following preparation process:
1), the preparation of molecular imprinting fluorescent polymer: tocopherol, quantum dot and function monomer are dissolved in chloroformic solution and are stirred 20～40 minutes, be preferably 30 minutes, add linking agent, initiator, pass into nitrogen 5～20min, be preferably 10min, thermopolymerization 12～36 hours in 40-80 DEG C of water-bath, be preferably in 60 DEG C of water-baths thermopolymerization 20 hours, obtain oyster white bulk polymer, after fully grinding, cross sub-sieve in mortar, be preferably 200 object sub-sieves, obtain powdery product;
2), the removal of masterplate molecule: by methanol solution Soxhlet extraction masterplate molecule, repeatable operation, until can not detect masterplate molecule, vacuum-drying, to constant weight, obtains tocopherol molecular imprinting fluorescent polymer.
Preferably, step 1) in, the mol ratio of tocopherol, quantum dot, function monomer, linking agent and initiator is 1:0.05:2-16:20-30:0.12-0.37.
Preferably, step 1) in, the mol ratio of tocopherol, quantum dot, function monomer, linking agent and initiator is 1:0.05:8:25:0.27.
The present invention also provides the application in the separation from complicated food substrate of a kind of fertility molecular imprinting fluorescent polymer as above, purifying or enrichment tocopherol.
The solution that contains tocopherol and described tocopherol molecular imprinting fluorescent polymer are carried out to the special absorption of selectivity, thereby reach the object of tocopherol described in purifying and rapid detection.
Advantage and positively effect that the invention has are:
1) the molecular imprinting fluorescent polymer that, the method in the present invention makes has the advantages such as regular shape, physical strength is high, detailed performance good, selective adsorption is effective, can be used for separation from the complicated food substrate such as grease, rice, purifying and enrichment tocopherol, have broad application prospects.
2), in the present invention, the preparation method of molecular imprinting fluorescent polymer is simple, craft science, with low cost, simple to operate, reaction conditions is gentle and be easy to control, can separate and rapid detection tocopherol by specific selectivity, for subsequent applications provides basis, its preparation method is simple and convenient, is suitable for large-scale promotion application.
Embodiment
The present invention combines molecular imprinting with quantum dot fluorescence nano material, synthetic have highly selective adsorption functional material to tocopherol, and its concrete preparation process is:
1), the preparation of molecular imprinting fluorescent polymer: the quantum dot of the template molecule tocopherol of 1mmol and 0.05mmol and function monomer are dissolved in 5.25mL chloroformic solution and are stirred 30 minutes, add linking agent, 45mg initiator, degassed, thermopolymerization 20 hours in 60 DEG C of water-baths, obtain oyster white bulk polymer, after fully grinding, cross 200 order sub-sieves in mortar, obtain powdery product;
2), the removal of masterplate molecule: by methanol solution Soxhlet extraction masterplate molecule, repeatable operation, until can not detect masterplate molecule, vacuum-drying, to constant weight, finally obtains the tocopherol molecular imprinting fluorescent polymer of size homogeneous.
Seven specific embodiments are provided, and in embodiment mono-～embodiment seven template molecule tocopherol, quantum dot, function monomer, linking agent concrete amount as shown in Table 1:
Table one
Respectively getting 10mL concentration is 1.0 × 10
-4mol L
-1tocopherol solution, the molecular imprinting fluorescent polymer that adds respectively 20mg above-described embodiment one～embodiment tetra-to adopt different mol ratio to prepare, the concentration of tocopherol in precipitation under mensuration different condition, calculate the loading capacity of polymkeric substance, and the trace factor, experimental result as shown in Table 2, along with the increase of mol ratio, molecular imprinting fluorescent polymer first reduces rear increase to the change in fluorescence amount of tocopherol, wherein with masterplate molecule: function monomer=1: 8 o'clock maximums.When mol ratio is lower, cannot form complete recognition site, can not practical function monomer and the multidigit point combination of template molecule; When mol ratio is higher, function monomer surplus, can cause non-specific adsorption to strengthen; Therefore select masterplate molecule: function monomer=1: 2～1: 16 is better synthetic mol ratio, select masterplate molecule: function monomer=1: 8 is best synthetic mol ratio.
Table two
Respectively getting 10mL concentration is 1.0 × 10
-4mol L
-1tocopherol solution, the molecular imprinting fluorescent polymer that adds respectively 20mg above-described embodiment five～embodiment seven to adopt different mol ratio to prepare, vibration absorption certain hour, carry out centrifugal (5000rpm, 10min), the concentration of tocopherol in precipitation under mensuration different condition, calculate the loading capacity of polymkeric substance, and the trace factor, experimental result as shown in Table 3, along with the increase of mol ratio, molecular imprinting fluorescent polymer first reduces rear increase to the change in fluorescence amount of tocopherol, wherein with masterplate molecule: linking agent=1: 25 o'clock maximums.When mol ratio is lower, cannot form the molecular imprinting fluorescent polymer of solid; When mol ratio is higher, linking agent surplus, can cause synthetic polymkeric substance diameter bigger than normal, and excessive linking agent parcel quantum dot can cause the fluorescence of quantum dot to reduce, thus the susceptibility that impact detects.Therefore select masterplate molecule: linking agent=1: 20～1: 30 is better synthetic mol ratio, select masterplate molecule: linking agent=1: 25 is best synthetic mol ratio.
The selection of table trimerization cross-linking reaction agent
Respectively get 20mg tocopherol molecular imprinting fluorescent polymer, add respectively 1.0 × 10
-4mol L
-1tocopherol solution 10ml, after mixing, vibration absorption, measures the concentration of tocopherol in primary sedimentation for every 30 minutes, calculates the unit adsorptive capacity of molecular imprinting fluorescent polymer to tocopherol under different time.Experimental result shows, in certain adsorption time, molecularly imprinted polymer increases along with the increase of adsorption time the absorption of tocopherol, and wherein, in the time that adsorption time is 7h, molecularly imprinted polymer is tending towards adsorption equilibrium to the absorption of tocopherol.Template molecule enters in molecularly imprinted polymer needs the regular hour, if the time is too short, molecularly imprinted polymer can not adsorb enough tocopherols; If adsorption time is oversize, can lowering efficiency, it is free even to have the desorb of part tocopherol molecule; Therefore select 7-8h for better adsorption time, selecting adsorption time is that 7h is the optimal adsorption time.
In order better to prove beneficial effect of the present invention, spy is provided with seven control groups, the quantum dot of 0.05mmol is dissolved in the solvent chloroform of 5.25mL, mixing mixes, according to the numerical value in table 1, add function monomer methacrylic acid, linking agent ethylene glycol dimethacrylate, and initiator Diisopropyl azodicarboxylate.After mixing, pass into nitrogen 10min, in the state lower seal reaction system of nitrogen.60 DEG C of reaction 20h; After polyreaction finishes, synthetic polymkeric substance is pulverized, grinds, sieved, then remove template molecule with methanol solution, until can't detect template molecule; The polymkeric substance of removing template molecule is dried, finally obtains the molecular imprinting fluorescent polymer of size homogeneous.
Adopt blank polymkeric substance to carry out determining of adsorption equilibrium, experimentation is with corresponding experimentation in embodiment, and result shows that the blank polymkeric substance of seven control groups is all without adsorptive power.
To sum up, tocopherol molecular imprinting fluorescent polymer of the present invention can separate tocopherol by specific selectivity, enrichment tocopherol, and for subsequent applications provides basis, its preparation method is simple and convenient, is suitable for large-scale promotion application.
Above the embodiment of the invention is had been described in detail, but described content is only for the preferred embodiment of the invention, can not be considered to for limiting practical range of the present invention.All equalization variation and improvement etc. of doing according to the invention scope, within all should still belonging to this patent covering scope.
Claims (7)
1. a tocopherol molecular imprinting fluorescent polymer, it is characterized in that: taking tocopherol as template molecule, add quantum dot fluorescent nano material, employing can form with masterplate molecule the function monomer of hydrogen bond, under linking agent and initiator existence, carry out heat polymerization preparation.
2. tocopherol molecular imprinting fluorescent polymer according to claim 1, is characterized in that: described function monomer is methacrylic acid; Described tocopherol is alpha-tocopherol; Described quantum dot fluorescence nano material is CdSe/ZnS quantum dot.
3. tocopherol molecular imprinting fluorescent polymer according to claim 1 and 2, is characterized in that: described linking agent is Ethylene glycol dimethacrylate; Described initiator is Diisopropyl azodicarboxylate.
4. a method of preparing the tocopherol molecular imprinting fluorescent polymer as described in claim 1～3 any one, is characterized in that: comprise following preparation process:
1), the preparation of molecular imprinting fluorescent polymer: tocopherol, quantum dot and function monomer are dissolved in chloroformic solution and are stirred 20～40 minutes, be preferably 30 minutes, add linking agent, initiator, pass into nitrogen 5～20min, be preferably 10min, thermopolymerization 12～36 hours in 40-80 DEG C of water-bath, be preferably in 60 DEG C of water-baths thermopolymerization 20 hours, obtain oyster white bulk polymer, after fully grinding, cross sub-sieve in mortar, be preferably 200 object sub-sieves, obtain powdery product;
2), the removal of masterplate molecule: by methanol solution Soxhlet extraction masterplate molecule, repeatable operation, until can not detect masterplate molecule, vacuum-drying, to constant weight, obtains tocopherol molecular imprinting fluorescent polymer.
5. the preparation method of tocopherol molecular imprinting fluorescent polymer according to claim 4, it is characterized in that: step 1) in, the mol ratio of tocopherol, quantum dot, function monomer, linking agent and initiator is 1:0.05:2-16:20-30:0.12-0.37.
6. according to the preparation method of the tocopherol molecular imprinting fluorescent polymer described in claim 4 or 5, it is characterized in that: step 1) in, the mol ratio of tocopherol, quantum dot, function monomer, linking agent and initiator is 1:0.05:8:25:0.27.
7. the application in fertility molecular imprinting fluorescent polymer claimed in claim 1 separation from complicated food substrate, purifying or enrichment tocopherol.
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Cited By (11)
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| CN104403045A (en) * | 2014-12-23 | 2015-03-11 | 吉首大学 | Preparation method of chlorogenic acid uniformly-imprinted microspheres |
| CN104629763A (en) * | 2015-02-09 | 2015-05-20 | 天津科技大学 | Sensing material based on up-conversion nanoparticle and preparation method of sensing material |
| CN104926981A (en) * | 2015-05-07 | 2015-09-23 | 天津科技大学 | Preparation method for fluorescence sensing material based on molecular imprinting and carbon dots |
| CN105259167A (en) * | 2015-11-30 | 2016-01-20 | 天津科技大学 | Preparation method and application of molecularly-imprinted electrochemiluminescence sensing material |
| CN105300948A (en) * | 2015-11-23 | 2016-02-03 | 天津科技大学 | Ochratoxins upconversion fluorescent sensing material and preparation method thereof |
| CN105693959A (en) * | 2016-01-29 | 2016-06-22 | 华南师范大学 | Preparation method of magnetic molecularly imprinted polymer with hydrogen bond array |
| CN109280125A (en) * | 2018-11-06 | 2019-01-29 | 武汉工程大学 | The preparation method and applications of vitamin E molecularly imprinted polymer |
| CN110818836A (en) * | 2019-11-21 | 2020-02-21 | 武汉工程大学 | Vitamin E molecularly imprinted polymer, two-step swelling preparation method and application thereof |
| CN111393568A (en) * | 2020-03-25 | 2020-07-10 | 合肥工业大学 | Tocopherol molecularly imprinted polymer, preparation method and application |
| CN111944191A (en) * | 2020-08-07 | 2020-11-17 | 武汉珈源同创科技有限公司 | Quantum dot fluorescent microsphere and preparation method thereof |
| CN113083339A (en) * | 2021-04-15 | 2021-07-09 | 万华化学(四川)有限公司 | Catalyst for preparing vitamin E and preparation method and application thereof |
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Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104403045A (en) * | 2014-12-23 | 2015-03-11 | 吉首大学 | Preparation method of chlorogenic acid uniformly-imprinted microspheres |
| CN104629763A (en) * | 2015-02-09 | 2015-05-20 | 天津科技大学 | Sensing material based on up-conversion nanoparticle and preparation method of sensing material |
| CN104926981A (en) * | 2015-05-07 | 2015-09-23 | 天津科技大学 | Preparation method for fluorescence sensing material based on molecular imprinting and carbon dots |
| CN105300948B (en) * | 2015-11-23 | 2018-05-22 | 天津科技大学 | A kind of ochratoxin up-conversion fluorescence sensing material and preparation method thereof |
| CN105300948A (en) * | 2015-11-23 | 2016-02-03 | 天津科技大学 | Ochratoxins upconversion fluorescent sensing material and preparation method thereof |
| CN105259167B (en) * | 2015-11-30 | 2018-05-18 | 天津科技大学 | A kind of molecular imprinting electrochemical shines the preparation method and application of sensing material |
| CN105259167A (en) * | 2015-11-30 | 2016-01-20 | 天津科技大学 | Preparation method and application of molecularly-imprinted electrochemiluminescence sensing material |
| CN105693959A (en) * | 2016-01-29 | 2016-06-22 | 华南师范大学 | Preparation method of magnetic molecularly imprinted polymer with hydrogen bond array |
| CN105693959B (en) * | 2016-01-29 | 2018-05-08 | 华南师范大学 | The preparation method of magnetic molecularly imprinted polymer with hydrogen bond array |
| CN109280125A (en) * | 2018-11-06 | 2019-01-29 | 武汉工程大学 | The preparation method and applications of vitamin E molecularly imprinted polymer |
| CN110818836A (en) * | 2019-11-21 | 2020-02-21 | 武汉工程大学 | Vitamin E molecularly imprinted polymer, two-step swelling preparation method and application thereof |
| CN111393568A (en) * | 2020-03-25 | 2020-07-10 | 合肥工业大学 | Tocopherol molecularly imprinted polymer, preparation method and application |
| CN111393568B (en) * | 2020-03-25 | 2022-04-01 | 合肥工业大学 | Tocopherol molecularly imprinted polymer, preparation method and application |
| CN111944191A (en) * | 2020-08-07 | 2020-11-17 | 武汉珈源同创科技有限公司 | Quantum dot fluorescent microsphere and preparation method thereof |
| CN111944191B (en) * | 2020-08-07 | 2023-04-25 | 武汉珈源同创科技有限公司 | Quantum dot fluorescent microsphere and preparation method thereof |
| CN113083339A (en) * | 2021-04-15 | 2021-07-09 | 万华化学(四川)有限公司 | Catalyst for preparing vitamin E and preparation method and application thereof |
| CN113083339B (en) * | 2021-04-15 | 2022-11-08 | 万华化学(四川)有限公司 | Catalyst for preparing vitamin E and preparation method and application thereof |
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Application publication date: 20140903 |