CN112649408A - Molecularly imprinted fluorescent sensor for quantitative detection of alkylresorcinol and preparation method thereof - Google Patents
Molecularly imprinted fluorescent sensor for quantitative detection of alkylresorcinol and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a molecularly imprinted fluorescent sensor for quantitatively detecting alkylresorcinol and a preparation method thereof, and relates to the technical field of chemical analysis. The preparation method comprises the following steps: (1) preparing a NaHTe aqueous solution; (2) preparing CdTe quantum dots; (3) preparing a molecularly imprinted fluorescent sensor: uniformly mixing the CdTe quantum dots obtained in the step (2) with a pore-foaming agent, and introducing N2Deoxidizing, adding ARs to react for 10-30min, adding functional monomer, cross-linking agent and ammonia water, introducing N2Stirring and reacting at 50-70 ℃ for 12-36h, removing ARs from the obtained precipitate after the reaction is finished, and drying to obtain the molecular imprinting fluorescence sensor. The fluorescence sensor disclosed by the invention is good in polymerization degree, can be used for quickly and effectively realizing quantitative detection of ARs, and is good in detection stability and high in selectivity.
Description
Technical Field
The invention relates to the technical field of chemical analysis, in particular to a molecularly imprinted fluorescent sensor for quantitatively detecting alkylresorcinol and a preparation method thereof.
Background
Alkylresorcinols (1, 3-dihydroxy-5-alkylbenzene derivatives, ARs) are a class of phenolic substances found in recent years, which are mainly present in wheat bran, triticale and other wheat crop bran, and are classified into different homologue components such as 5-heptadecyresorcinols (C17:0), 5-nonadecylresorcinol (C19:0), 5-heneicosylresorcinols (C21:0), 5-tricosylresorcinols (C23:0), 5-pentacosylresorcinol (C25:0) and the like, depending on the number of carbon atoms in the saturated alkyl side chain. ARs are less present in the embryo and endosperm and are therefore identified as whole wheat product markers. With the health effects of whole grain supported by more and more evidence, 2016's version of the Chinese resident ' dietary guide ' advocates residents to increase the intake of whole grain, and food products on the market claiming "whole grain" are increasing. The quality of the whole grain product can be effectively judged, and the establishment of a quantitative analysis method of the marker ARs of the whole grain product is of great significance.
In recent decades, various methods for detecting ARs have been developed, such as spectrophotometry, combined gas chromatography-mass spectrometry, combined high performance liquid chromatography-mass spectrometry, and the like. However, pretreatment before sample detection by chromatography is complex, and the instrument is expensive, which is not favorable for popularization and use of chromatography; the spectrum method is easily interfered by colored substances in a sample, the error of an analysis result is large, and the application difficulty of the spectrum method is increased. Meanwhile, the detection limits and the linear ranges of the method are different, and the defects of low identification efficiency, poor selectivity, low sensitivity, weak signals and the like exist. Therefore, the existing detection method limits the rapid and simple quantitative detection of ARs in the whole grain, and is difficult to provide support for the authenticity judgment of the domestic whole grain food.
Molecular Imprinting Technology (MIT) refers to a technique for preparing a polymer having a specific recognition site and a predetermined selectivity, and the synthesized polymer can selectively adsorb a template molecule or a family of compounds having a similar structure to the template molecule. In recent years, a fluorescence sensor developed based on quantum dots has the characteristics of low cost, simplicity in operation and the like, and is widely applied to environment and food detection. The CdTe quantum dot has excellent optical performance, biocompatibility and easy modification, is one excellent fluorescent material and may be used widely in biomarker, sensor, photoelectronic material and other fields. The molecular imprinting technology is introduced to enhance the specificity recognition capability of the CdTe quantum dots, and meanwhile, the stability of quantum dot fluorescence is greatly improved due to the formation of the surface imprinting layer, so that the method has the advantages of high sensitivity, simple fluorescence detection mechanism and the like. Generally, a fluorescence signal is often used as a signal for detecting a trace substance, and when the template molecule is adsorbed to a binding site and the fluorescent substance can interact with each other to cause a change in fluorescence of the fluorescent group, the amount of the template molecule can be analyzed by the fluorescence intensity.
For example, Chinese patent application 201510124191.7 discloses a preparation method of a CdTe quantum dot fluorescent cyhalothrin imprinted sensor, belonging to the technical field of preparation of environmental functional materials; firstly, preparing a precursor NaHTe solution; then injecting the precursor solution into CdCl 2.25H2O aqueous solution which is filled with nitrogen and deoxidized and has thioglycollic acid, and carrying out reflux reaction under the condition of nitrogen protection to obtain CdTe quantum dots; then, phase conversion is carried out on the CdTe quantum dots to a chloroform phase by utilizing a polymerizable surfactant OVDAC, so as to obtain the CdTe quantum dots modified by the OVDAC; and finally, synthesizing the CdTe quantum dot fluorescent molecularly imprinted polymer taking the OVDAC modified CdTe quantum dot as a fluorescent carrier by using a precipitation polymerization method, and using the CdTe quantum dot fluorescent molecularly imprinted polymer for optically detecting the cyhalothrin.
However, a molecularly imprinted fluorescent sensor for detecting ARs is lacking at present, so that the ARs in the whole grain can be rapidly and easily detected quantitatively. In view of the above, the present application combines the advantages of the surface molecular imprinting technology and the fluorescence detection technology to prepare an analytical and quantitative technology based on the specificity recognition of ARs. The prepared CdTe quantum dot shows a certain fluorescent response to ARs, namely the fluorescent intensity of the quantum dot can be quenched by the ARs. The molecular imprinting fluorescence sensor has good stability and strong repeatability, has higher sensitivity and lower detection limit when applied to the fluorescence quantitative detection of the ARs, has stronger selective recognition capability on the ARs, reliably realizes the quantitative detection and analysis of the ARs in the detection range, and establishes a new detection method to improve the sensitivity, accuracy and detection efficiency of the quantitative detection of the ARs.
Disclosure of Invention
The invention aims to prepare a novel molecular imprinting fluorescence sensor with higher adsorption capacity and recognition capacity and high sensitivity by utilizing a simple fluorescence mechanism based on a molecular imprinting technology and a fluorescence detection technology, and is applied to quantitative analysis and detection of a target analyte in an actual sample to reliably realize quantitative detection and analysis of ARs in a detection range.
In order to achieve the purpose, the technical scheme of the invention is as follows:
firstly, the invention provides a preparation method of a molecularly imprinted fluorescent sensor for quantitative detection of alkylresorcinol, which comprises the following steps:
(1) preparation of aqueous NaHTe solution: tellurium powder and NaBH4Mixing the mixture with secondary distilled water to obtain a mixed system, introducing nitrogen, heating and stirring the mixed system at 60-120 ℃, continuously introducing nitrogen, and stopping reaction to obtain supernatant, namely the NaHTe aqueous solution;
(2) preparing CdTe quantum dots: adding CdCl2·2.5H2Mixing O, secondary distilled water and a stabilizer, carrying out ultrasonic dissolution to obtain a mixed solution, adjusting the pH value of the mixed solution to 10.2-11.2, introducing nitrogen for protection, heating the mixed solution to 60-150 ℃, adding the NaHTe aqueous solution obtained in the step (1), removing nitrogen, and carrying out heating reflux to obtain CdTe quantum dots;
(3) preparing a molecularly imprinted fluorescent sensor: uniformly mixing the CdTe quantum dots obtained in the step (2) with a pore-foaming agent, and introducing N2Deoxidizing, adding ARs to react for 10-30min, adding functional monomer, cross-linking agent and ammonia water, introducing N2Stirring and reacting at 50-70 ℃ for 12-36h, removing ARs from the obtained precipitate after the reaction is finished, and drying to obtain the molecular imprinting fluorescence sensor.
Preferably, in the step (1), the tellurium powder and NaBH are mixed4Is 1: 2-6.
Preferably, in the step (1), the nitrogen is introduced for 10-30 min.
Preferably, in the step (1), the continuous nitrogen gas introduction time is 20-60 min.
Preferably, in the step (2), the CdCl2The molar ratio of stabilizer to NaHTe is 1: 2-4: 0.5-1.
Preferably, in the step (2), the stabilizer is at least one of mercaptoethylamine, mercaptopropionic acid, thioglycolic acid and glutathione.
Preferably, in the step (2), the pH value is adjusted by using 0.1mol/L NaOH solution.
Preferably, in the step (3), the porogen is selected from at least one of ethanol, acetonitrile, methanol or chloroform.
Preferably, in the step (3), the dosage ratio of the ARs, the CdTe quantum dots, the functional monomer and the cross-linking agent is 0.02 mmol: 2-30 mL: 0.05-0.1 mmol: 0.2-0.4 mmol.
Preferably, in the step (3), the uniformly mixing of the CdTe quantum dots and the pore-forming agent specifically comprises: and (3) putting the CdTe quantum dots into a rotary evaporator until water evaporation is finished, washing the rotary evaporated substances into a three-neck flask by using a pore-forming agent, and uniformly dispersing by using ultrasound.
Preferably, in step (3), the reaction is performed under N2The time for removing oxygen is 10-30 min.
Preferably, in the step (3), the functional monomer is Aminopropyltriethoxysilane (APTES).
Preferably, in the step (3), the cross-linking agent is tetraethyl orthosilicate (TEOS).
In still another aspect, the present invention provides a molecularly imprinted fluorescent sensor prepared according to the above preparation method.
Compared with the prior art, the invention has the following beneficial effects:
the fluorescence sensor prepared by the preparation method disclosed by the invention is good in polymerization degree, can be used for quickly and effectively realizing quantitative detection of ARs, and is good in detection stability and high in selectivity.
Drawings
FIG. 1 is a transmission electron micrograph of a molecularly imprinted fluorescent sensor according to example 1 of the present invention;
FIG. 2 is a scanning electron micrograph of a molecularly imprinted fluorescent sensor according to comparative example 1 of the present invention;
FIG. 3 is a fluorescence spectrum (a) of a molecularly imprinted fluorescent sensor according to example 2 of the present invention in combination with ARs and a fluorescence spectrum (b) of the molecularly imprinted fluorescent sensor;
FIG. 4 is a fluorescence spectrum (a) of a molecularly imprinted fluorescent sensor of comparative example 2 of the present invention in combination with ARs and a fluorescence spectrum (b) of the molecularly imprinted fluorescent sensor;
FIG. 5 is a graph showing the time stability of fluorescence intensity of the molecularly imprinted fluorescent sensor of example 2 of the present invention;
FIG. 6 is a graph showing the time stability of fluorescence intensity of the molecularly imprinted fluorescent sensor of comparative example 2 of the present invention;
FIG. 7 is a diagram showing the selective adsorption of ARs by the molecularly imprinted fluorescent sensor of example 3 of the present invention;
FIG. 8 is a schematic diagram showing the selective adsorption of ARs by the molecularly imprinted fluorescent sensor of comparative example 3 of the present invention.
Detailed Description
The present invention will be further explained with reference to specific examples in order to make the technical means, the technical features, the technical objectives and the effects of the present invention easier to understand, but the following examples are only preferred embodiments of the present invention, and not all embodiments of the present invention. In the interest of clarity, not all features of an actual implementation are described. In the following description, well-known functions or constructions are not described in detail since they would obscure the invention in unnecessary detail. It will of course be appreciated that in the development of any such actual embodiment, numerous implementation-specific details must be set forth in order to achieve the developer's specific goals. Based on the embodiments in the implementation, other embodiments obtained by those skilled in the art without any creative efforts belong to the protection scope of the present invention.
The experimental methods in the following examples are conventional methods unless otherwise specified, and materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
Example 1
(1) Adding into a dry three-neck flaskAdding 80mg of tellurium powder and 50mg of NaBH4And 1.0mL of secondary distilled water, introducing nitrogen for 10min, then placing the three-neck flask into a constant-temperature water bath at 60 ℃, heating and stirring, keeping introducing nitrogen, stopping reaction after 20min, and obtaining a supernatant, namely the NaHTe aqueous solution.
(2) Preparing CdTe quantum dots: 0.2864g of CdCl2·2.5H2O, 100mL of redistilled water and 0.097g of mercaptoethylamine are put into another clean three-neck flask, dissolved by ultrasonic, the pH value of the solution is adjusted to 10.2 by 0.1mol/L of NaOH, and nitrogen is introduced for protection. Heating the mixture in a constant-temperature water bath to 60 ℃, adding the newly prepared NaHTe aqueous solution into the flask, placing the flask in the water bath, removing nitrogen, and heating and refluxing.
(3) Preparing a molecularly imprinted fluorescent sensor: putting 2mL of CdTe quantum dots into a rotary evaporator until water evaporation is finished, washing the rotary evaporated material into a three-neck flask by using ethanol, ultrasonically dispersing uniformly, and introducing N2And (5) deoxidizing for 10 min. Accurately weighing 0.02mmol of ARs, adding the ARs into the ethanol containing the CdTe quantum dots, stirring for reaction for 10min, and sequentially adding 0.05mmol of APTES (aminopropyltriethoxysilane), 0.2mmol of TEOS (tetraethyl orthosilicate) and 0.8g of 25% ammonia water by volume fraction after template molecules are uniformly mixed. General formula (N)2The reaction was stirred at 50 ℃ for 12 h. After the reaction is finished, the ARs in the molecularly imprinted polymer are removed from the precipitate, and finally, the molecularly imprinted polymer is dried in vacuum to balance weight.
Example 2
(1) Preparation of aqueous NaHTe solution: 50.8mg of tellurium powder and 60.53mg of NaBH were placed in a dry three-necked flask4And 10mL of secondary distilled water, introducing nitrogen for 20min, placing the three-neck flask into a constant-temperature water bath at 90 ℃, heating and stirring, keeping introducing nitrogen, stopping reaction after 40min, and obtaining a supernatant, namely the NaHTe aqueous solution.
(2) Preparing CdTe quantum dots: 45.67mg of CdCl2·2.5H2O, 40mL of redistilled water and 0.021g of mercaptopropionic acid are put into another clean three-necked flask, dissolved by ultrasonic waves, the pH value of the solution is adjusted to 10.6 by 0.1mol/L of NaOH, and nitrogen is introduced for protection. Heating in constant temperature water bath to 105 deg.C, adding newly prepared NaHTe aqueous solution into flask, placing flask in water bath, removing nitrogen, heatingAnd (4) streaming.
(3) Preparing a molecularly imprinted fluorescent sensor: taking 15mL of CdTe quantum dots to a rotary evaporator until water is evaporated, washing the rotary evaporated material to a three-neck flask by using methanol, ultrasonically dispersing uniformly, and introducing N2And (5) deoxidizing for 20 min. Accurately weighing 0.02mmol of ARs, adding the ARs into the methanol containing the CdTe quantum dots, stirring for reaction for 20min, and sequentially adding 0.075mmol of APTES, 0.3mmol of TEOS and 2g of ammonia water with volume fraction of 25% after template molecules are uniformly mixed. General formula (N)2The reaction was stirred at 60 ℃ for 24 h. After the reaction is finished, the ARs in the molecularly imprinted polymer are removed from the precipitate, and finally, the molecularly imprinted polymer is dried in vacuum to balance weight.
Example 3
(1) Preparation of aqueous NaHTe solution: 60mg of tellurium powder and 0.113g of NaBH were placed in a dry three-necked flask4And 10mL of secondary distilled water, introducing nitrogen for 20min, placing the three-neck flask into a 120 ℃ constant-temperature water bath, heating and stirring, keeping introducing nitrogen, stopping reaction after 60min, and obtaining a supernatant, namely the NaHTe aqueous solution.
(2) Preparing CdTe quantum dots: 0.228g of CdCl2·2.5H2O, 100mL of redistilled water and 0.18g of thioglycolic acid are put into another clean three-neck flask, dissolved by ultrasonic waves, the pH value of the solution is adjusted to 11.2 by 0.1mol/L of NaOH, and nitrogen is introduced for protection. Heating the mixture in a constant-temperature water bath to 150 ℃, adding the newly prepared NaHTe aqueous solution into the flask, placing the flask in the water bath, removing nitrogen, and heating and refluxing.
(3) Preparing a molecularly imprinted fluorescent sensor: putting 30mLCdTe quantum dots into a rotary evaporator until water evaporation is finished, washing the rotary evaporated substance into a three-neck flask by using a pore-forming agent, ultrasonically dispersing uniformly, and introducing N2And (4) deoxidizing for 30 min. Accurately weighing 0.02mmol of ARs, adding the ARs into the pore-foaming agent containing the CdTe quantum dots, stirring for reaction for 30min, and sequentially adding 0.1mmol of APTES, 0.4mmol of TEOS and 4g of ammonia water with volume fraction of 25% after template molecules are uniformly mixed. General formula (N)2The reaction was stirred at 70 ℃ for 36 h. After the reaction is finished, the ARs in the molecularly imprinted polymer are removed from the precipitate, and finally, the molecularly imprinted polymer is dried in vacuum to balance weight.
Comparative example 1
In contrast to example 1, 0.2mmol of APTES and 0.5mmol of TEOS were added, the rest being identical.
Comparative example 2
In contrast to example 2, 0.2mmol of APTES and 0.5mmol of TEOS were added, the rest being identical.
Comparative example 3
In contrast to example 3, 0.2mmol of APTES and 0.5mmol of TEOS were added, the rest being identical.
Analysis of results
Fig. 1 is a Scanning Electron Microscope (SEM) image of the molecularly imprinted fluorescent sensor obtained in example 1, from which the size, morphology and distribution of the CdTe quantum dot fluorescent sensor can be seen, and at the same time, the successful synthesis and good polymerization degree of the CdTe quantum dot fluorescent sensor are demonstrated.
FIG. 2 is a Scanning Electron Micrograph (SEM) of the molecularly imprinted fluorescent sensor obtained in comparative example 1. When the dosage of the functional monomer and the cross-linking agent is increased, the particle size is not uniform, and a strong aggregation phenomenon occurs to influence the appearance of the molecular imprinting fluorescent sensor.
FIG. 3 is a fluorescence spectrum (a) of the molecularly imprinted fluorescent sensor in example 2 in combination with ARs and a fluorescence spectrum (b) of the molecularly imprinted fluorescent sensor. In the presence of ARs, the fluorescence intensity of the molecularly imprinted fluorescent sensor is greatly reduced; in the absence of ARs, the fluorescence intensity of the molecularly imprinted fluorescent sensor is recovered, indicating that the fluorescence intensity of the CdTe quantum dots can be quenched by ARs. When ARs are adsorbed to the binding sites to interact with CdTe quantum dots and cause the fluorescence of the fluorescent groups to change, the content of the ARs can be analyzed through the fluorescence intensity.
FIG. 4 is a fluorescence spectrum (a) of the molecularly imprinted fluorescent sensor obtained in comparative example 2 in combination with ARs and a fluorescence spectrum (b) of the molecularly imprinted fluorescent sensor. Compared with the graph in FIG. 3, when the amount of the functional monomer and the cross-linking agent is increased, the fluorescence intensity of the molecularly imprinted fluorescent sensor combined with the ARs and the molecularly imprinted fluorescent sensor is remarkably reduced, which indicates that excessive functional monomer and cross-linking agent have influence on the fluorescence performance of the molecularly imprinted.
FIG. 5 shows the stability of the molecularly imprinted fluorescent sensor synthesized in example 2. The fluorescence emission spectrum is measured once at intervals of 30min for 7 times in total, and as shown in FIG. 5, the relative standard deviation of the fluorescence intensity measured for 7 times is calculated to be 3%, which indicates that the fluorescence stability of the molecularly imprinted fluorescent sensor is good.
FIG. 6 shows the stability of the synthesized molecularly imprinted fluorescent sensor of comparative example 2. The stability of the molecularly imprinted fluorescent sensor synthesized by the comparative example is better, and compared with FIG. 5, the fluorescence intensity is reduced, which shows that the fluorescence performance of the molecularly imprinted fluorescent sensor is influenced by excessive functional monomers and crosslinking agents.
FIG. 7 shows the results of selective adsorption of ARs, ferulic acid, coumaric acid and phytic acid by the molecularly imprinted fluorescent sensor in example 3. As can be seen from the figure, the molecularly imprinted fluorescent sensor has higher adsorption capacity to ARs, and the adsorption capacity to ferulic acid, coumaric acid and phytic acid is almost 0, which indicates that the recognition capability of the molecularly imprinted fluorescent sensor is based on the size, shape and three-dimensional structure of a cavity formed after the template is eluted, and further indicates that the molecularly imprinted fluorescent sensor has better selectivity to ARs.
FIG. 8 shows the results of selective adsorption of ARs, ferulic acid, coumaric acid and phytic acid by the molecularly imprinted fluorescent sensor synthesized in comparative example 3. As can be seen from the figure, the comparative example molecularly imprinted fluorescent sensor also has better selectivity for ARs, but the adsorption amounts of ARs, ferulic acid, coumaric acid and phytic acid are significantly reduced compared with the molecularly imprinted fluorescent sensor of example 3.
The present invention is not limited to the above-described preferred embodiments, but rather, the present invention is to be construed broadly and cover all modifications, equivalents, and improvements falling within the spirit and scope of the present invention.
Claims (10)
1. A preparation method of a molecularly imprinted fluorescent sensor for quantitative detection of alkylresorcinol is characterized by comprising the following steps:
(1) preparation of aqueous NaHTe solution: tellurium powder and NaBH4Mixing with redistilled water to obtain mixed system, introducing nitrogen, and adding the mixed system to 6Heating and stirring at 0-120 ℃, continuously introducing nitrogen, stopping the reaction, and obtaining supernatant, namely the NaHTe aqueous solution;
(2) preparing CdTe quantum dots: adding CdCl2·2.5H2Mixing O, secondary distilled water and a stabilizer, carrying out ultrasonic dissolution to obtain a mixed solution, adjusting the pH value of the mixed solution to 10.2-11.2, introducing nitrogen for protection, heating the mixed solution to 60-150 ℃, adding the NaHTe aqueous solution obtained in the step (1), removing nitrogen, and carrying out heating reflux to obtain CdTe quantum dots;
(3) preparing a molecularly imprinted fluorescent sensor: uniformly mixing the CdTe quantum dots obtained in the step (2) with a pore-foaming agent, and introducing N2Deoxidizing, adding ARs to react for 10-30min, adding functional monomer, cross-linking agent and ammonia water, introducing N2Stirring and reacting at 50-70 ℃ for 12-36h, removing ARs from the obtained precipitate after the reaction is finished, and drying to obtain the molecular imprinting fluorescence sensor.
2. The method according to claim 1, wherein in step (1), the tellurium powder is mixed with NaBH4Is 1: 2-6.
3. The method according to claim 1, wherein in the step (2), the CdCl2The molar ratio of stabilizer to NaHTe is 1: 2-4: 0.5-1.
4. The method according to claim 1, wherein in the step (2), the stabilizer is at least one of mercaptoethylamine, mercaptopropionic acid, thioglycolic acid, and glutathione.
5. The method according to claim 1, wherein in the step (3), the porogen is selected from at least one of ethanol, acetonitrile, methanol or chloroform.
6. The preparation method according to claim 1, wherein in the step (3), the dosage ratio of the ARs, the CdTe quantum dots, the functional monomer and the cross-linking agent is 0.02 mmol: 2-30 mL: 0.05-0.1 mmol: 0.2-0.4 mmol.
7. The preparation method according to claim 1, wherein in the step (3), the uniformly mixing of the CdTe quantum dots and the pore-forming agent is specifically as follows: and (3) putting the CdTe quantum dots into a rotary evaporator until water evaporation is finished, washing the rotary evaporated substances into a three-neck flask by using a pore-forming agent, and uniformly dispersing by using ultrasound.
8. The method according to claim 1, wherein in the step (3), the functional monomer is aminopropyltriethoxysilane.
9. The method according to claim 1, wherein in the step (3), the crosslinking agent is tetraethoxysilane.
10. A molecularly imprinted fluorescent sensor prepared according to the preparation method of any one of claims 1 to 10.
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Citations (3)
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|---|---|---|---|---|
| CN103539945A (en) * | 2013-09-29 | 2014-01-29 | 南京医科大学 | P-aminophenol imprinted polymer on surface of cadmium telluride quantum dot as well as preparation method and application thereof |
| CN109553510A (en) * | 2018-09-30 | 2019-04-02 | 北京工商大学 | Alkyl-resorcin class compound and application thereof |
| CN109932336A (en) * | 2019-04-26 | 2019-06-25 | 中国疾病预防控制中心营养与健康所 | A kind of method for quick identification of wholemeal |
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2020
- 2020-12-22 CN CN202011525136.6A patent/CN112649408A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103539945A (en) * | 2013-09-29 | 2014-01-29 | 南京医科大学 | P-aminophenol imprinted polymer on surface of cadmium telluride quantum dot as well as preparation method and application thereof |
| CN109553510A (en) * | 2018-09-30 | 2019-04-02 | 北京工商大学 | Alkyl-resorcin class compound and application thereof |
| CN109932336A (en) * | 2019-04-26 | 2019-06-25 | 中国疾病预防控制中心营养与健康所 | A kind of method for quick identification of wholemeal |
Non-Patent Citations (3)
| Title |
|---|
| ROBERT A. MOREAU ET AL: "Analysis of Alkylresorcinols in Wheat Germ Oil and Barley Germ Oil via HPLC and Fluorescence Detection: Cochromatography with Tocols", 《CEREAL CHEMISTRY》 * |
| 王建玲 等: "间苯二酚分子印迹聚合物的合成及其吸附性能研究", 《河南师范大学学报（自然科学版）》 * |
| 路霞林: "碲化镉量子点表面对氨基酚印迹聚合物的制备及其在对氨基酚检测中的应用", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
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Application publication date: 20210413 |