CN111518554B - Copper-doped carbon quantum dot with mimic enzyme property and preparation method and application thereof - Google Patents

Copper-doped carbon quantum dot with mimic enzyme property and preparation method and application thereof Download PDF

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CN111518554B
CN111518554B CN202010350764.9A CN202010350764A CN111518554B CN 111518554 B CN111518554 B CN 111518554B CN 202010350764 A CN202010350764 A CN 202010350764A CN 111518554 B CN111518554 B CN 111518554B
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杜金艳
漆双庆
范婷婷
杨影
王超峰
舒琴
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Anhui Normal University
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Abstract

The invention relates to the field of nano material catalytic sensing, and discloses a copper-doped carbon quantum dot with simulated enzyme property, a preparation method and application thereof, wherein the preparation method comprises the following steps: and mixing ascorbic acid, EDC, copper acetate and water, and carrying out hydrothermal reaction to obtain the copper-doped carbon quantum dot. The method solves the problems that the existing phenol detection method is complex, time-consuming and high in cost, and cannot realize on-site real-time detection.

Description

Copper-doped carbon quantum dot with mimic enzyme property and preparation method and application thereof
Technical Field
The invention relates to the field of nano material catalytic sensing, in particular to a copper-doped carbon quantum dot with simulated enzyme properties and a preparation method and application thereof.
Background
Nanomaterials have been the focus of research as mimetic enzymes, and scientists have been striving to use the simplest structures of compounds as mimetic enzymes. As a novel nano fluorescent material, the carbon quantum dots have excellent performance in the fields of fluorescence sensing, catalysis and the like. Importantly, the carbon quantum dot serving as the mimic enzyme can provide an indication signal for a catalytic process by virtue of the fluorescence property of the carbon quantum dot, so that the interference of an additional indicator is effectively avoided, and a new method is provided for the difficult problem that the signal is difficult to capture in the catalytic reaction process.
Phenol is an important raw material in the chemical industry for manufacturing petrochemical, pharmaceutical, plastic and pesticide materials, and is also an important pollutant in the environment and water, so accurately determining the concentration of phenol in water is critical to both the industrial and natural environments. At present, various methods such as a liquid chromatography method, a capillary electrophoresis method, a spectrophotometry method and the like are mainly used for detecting phenol. Although these techniques have high sensitivity and reproducibility, these methods are complex, time consuming and expensive to operate, and do not allow for on-site real-time detection.
Disclosure of Invention
The invention aims to provide a copper-doped carbon quantum dot with a mimic enzyme property, and a preparation method and application thereof, and solves the problems that the existing phenol detection method is complex, time-consuming and high in cost, and cannot realize field real-time detection.
In order to achieve the above object, the present invention provides a method for preparing a copper-doped carbon quantum dot having mimic enzyme properties, the method comprising: and mixing ascorbic acid, EDC, copper acetate and water, and carrying out hydrothermal reaction to obtain the copper-doped carbon quantum dot.
The invention also provides the copper-doped carbon quantum dot with the mimic enzyme property, and the copper-doped carbon quantum dot is prepared by the preparation method.
The invention also provides a method for measuring the concentration of phenol by using the copper-doped carbon quantum dot, which comprises the following steps:
(1) Mixing phenol and a blank solution to be detected to obtain a solution to be detected; wherein the blank solution to be tested is carbonate buffer solution and H 2 O 2 4-APP and copper-doped carbon quantum dots are mixed to obtain the composite material;
(2) Respectively measuring the maximum fluorescence intensity of a blank solution to be measured and a solution to be measured;
(3) Establishing a fluorescence emission spectrum curve equation by taking the ratio of the maximum fluorescence intensity of the solution to be detected to the maximum fluorescence intensity of the blank solution to be detected as a vertical coordinate and the concentration of phenol as a horizontal coordinate;
(4) The maximum fluorescence intensity of the phenol is measured, and then the concentration of the phenol is calculated according to a fluorescence emission spectrum curve equation.
According to the technical scheme, the invention provides a method for preparing copper-doped carbon quantum dots by a one-pot hydrothermal carbonization method, which is characterized in that in a closed high-temperature high-pressure reaction kettle, secondary distilled water is used as a reaction solvent, ascorbic acid, EDC and copper acetate are added, and a closed high-temperature high-pressure chemical reaction environment is generated by heating to prepare the copper-doped carbon quantum dots.Effect of EDC during the reaction: (1) as a carbon source for synthesizing copper-doped carbon quantum dots; (2) as a chelating agent for copper acetate; ascorbic acid as a reducing agent; the copper acetate serves as a metal dopant to synthesize the copper-doped carbon quantum dots. The catalyst provided by the invention is different from the metal complex reported previously, the catalyst does not need to be dissolved by an organic solvent, and the synthesized catalyst has a bifunctional property, and can catalyze and indicate H 2 O 2 And 4-APP and phenol color reaction, and a new phenol double-parameter catalytic sensing method is constructed based on ultraviolet absorption of the product and fluorescence spectrum change of the copper-doped carbon quantum dots. By controlling the dosage and concentration of the raw materials and the reaction temperature and time, the invention prepares the copper-doped carbon quantum with uniform appearance, high fluorescence quantum yield, good dispersibility, low production cost, good reproducibility and controllability. The copper-doped carbon quantum dot prepared by the method is used as a mimic enzyme, has size advantages, strong quantum confinement and edge effects, and has excellent luminescence performance similar to that of the quantum dot.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention and not to limit the invention. In the drawings:
fig. 1 is (a) Transmission Electron Micrograph (TEM) and (B) size distribution histograms of copper-doped carbon quantum dots prepared in example 1;
fig. 2 is a Fluorescence excitation dependency graph (Fluorescence) of the copper-doped carbon quantum dots prepared in example 1;
fig. 3 is a uv absorption graph (Absorbance) of the copper-doped carbon quantum dot prepared in example 1;
FIG. 4 is a graph comparing the catalytic reaction effects of copper-doped carbon quantum dots prepared at different reaction temperatures in examples 1-3;
FIG. 5 is a fluorescence emission spectrum of phenol using the copper-doped carbon quantum dots prepared in example 1;
FIG. 6 is a linear graph of fluorescence intensity of phenol detected using the copper-doped carbon quantum dots prepared in example 1;
FIG. 7 is a UV absorption spectrum of phenol using the copper-doped carbon quantum dots prepared in example 1;
FIG. 8 is a linear graph of UV absorption intensity of phenol using the copper-doped carbon quantum dots prepared in example 1;
FIG. 9 is a schematic view showing the color development of a copper-doped carbon quantum dot detection phenol prepared in example 1;
FIG. 10 is a color development contrast diagram of copper-doped carbon quantum dot detection phenol and its isomers prepared in comparative example 1;
fig. 11 is a color development contrast diagram of selective detection of phenol by the copper-doped carbon quantum dots prepared in comparative example 2.
Detailed Description
The following describes in detail specific embodiments of the present invention. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
The invention provides a preparation method of a copper-doped carbon quantum dot with mimic enzyme property, which comprises the following steps: and mixing ascorbic acid, EDC, copper acetate and water, and performing hydrothermal reaction to obtain the copper-doped carbon quantum dot.
In a preferred embodiment of the present invention, the ascorbic acid is used in an amount of 0.03 to 0.05mol, the EDC is used in an amount of 2.5 to 2.7mol, and the copper acetate is used in an amount of 2.3 to 2.5mol, relative to 1L of water.
In a preferred embodiment of the present invention, the conditions of the hydrothermal reaction include: the temperature is 200-240 ℃; and/or for a period of 7-9 hours.
In a preferred embodiment of the invention, the mixing time is 20-40min.
The invention also provides a copper-doped carbon quantum dot with mimic enzyme properties, which is prepared by the preparation method of any one of claims 1 to 4.
The invention also provides a method for measuring the concentration of phenol by using the copper-doped carbon quantum dot, which comprises the following steps:
(1) Mixing phenol and a blank solution to be detected to obtain a solution to be detected; wherein the blank solution to be tested is carbonate buffer solution and H 2 O 2 4-APP and copper-doped carbon quantum dots are mixed to obtain the composite material;
(2) Respectively measuring the maximum fluorescence intensity of a blank solution to be measured and a solution to be measured;
(3) Establishing a fluorescence emission spectrum curve equation by taking the ratio of the maximum fluorescence intensity of the solution to be detected to the maximum fluorescence intensity of the blank solution to be detected as a vertical coordinate and the concentration of phenol as a horizontal coordinate;
(4) The maximum fluorescence intensity of the phenol is measured, and then the concentration of the phenol is calculated according to a fluorescence emission spectrum curve equation.
The following examples are given to illustrate the present invention.
Example 1
Weighing 0.3g of copper acetate, dissolving the copper acetate in 25mL of secondary distilled water, performing ultrasonic dissolution, adding ascorbic acid, weighing 0.3g of EDC in the solution, and stirring for 30 minutes to obtain a uniform mixed solution, wherein the concentration of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDC) in the mixed solution is 0.065mol/L, the concentration of copper acetate is 0.06mol/L, and the concentration of ascorbic acid is 1.6mol/L;
transferring the mixed solution into a 50mL stainless steel polytetrafluoroethylene high-temperature reaction kettle, carrying out hydrothermal reaction at 220 ℃ for 8h, taking out the reaction kettle, naturally cooling to room temperature, then, collecting a product by centrifugation, dialyzing for 5h by using a 1000Da dialysis bag, and storing in a refrigerator at 4 ℃ for later use, wherein a TEM image is shown in figure 1, and the TEM image shows that the copper-doped carbon quantum dots are uniformly dispersed in size, are close to spherical particles, have the average size within 3nm and are consistent with the size distribution characteristics of carbon nano materials. From the fluorescence excitation dependence graph (fig. 2) and the absorption spectrum graph (fig. 3) of the copper-doped carbon quantum dot, it can be seen that the prepared copper-doped carbon quantum dot is consistent with the previously reported characteristics of the carbon quantum dot.
Example 2
The procedure was as in example 1, except that the hydrothermal reaction conditions included: the temperature is 240 ℃ and the time is 8h.
Example 3
The procedure was as in example 1, except that the hydrothermal reaction conditions included: the temperature is 200 ℃ and the time is 8h. The prepared copper-doped carbon quantum dot is used for monitoring phenol, the temperature of the hydrothermal reaction of the copper-doped carbon quantum dot is selected as shown in figure 4, and the effect of the doped carbon quantum dot under the condition of 220 ℃ is best as shown in figure 4, so that 220 ℃ is selected as the optimal temperature.
Example 4
800uL of carbonate buffer solution (0.01 mol/L, pH = 10.0) was measured and the above 400uL of purified copper-doped carbon quantum dot solution (the content of copper-doped carbon quantum dots was 7.2 × 10) -5 g/L)、5mM 4-AAP(200μL)、0.5mM H 2 O 2 (200. Mu.L) and 20uL of phenol solution with different concentrations are sequentially added into a 2mL centrifuge tube, the volume is determined, and the mixture is shaken and mixed evenly. Standing at 25 deg.C for 3min, and measuring fluorescence emission spectrum of the reaction solution as shown in FIG. 5;
with carbonate buffer solution, H 2 O 2 Mixing 4-APP and the purified copper-doped carbon quantum dot solution, fixing the volume to 2mL to obtain a blank solution to be detected, establishing a fluorescence emission spectrum curve equation by taking the ratio of the maximum fluorescence intensity of the added phenol solutions with different concentrations to the maximum fluorescence intensity of the blank solution to be detected as a vertical coordinate and the concentration of phenol as a horizontal coordinate, and obtaining a fluorescence emission spectrum curve equation Y = -0.439 multiplied by 10 -2 [PA]+1.0018 (Y represents the fluorescence intensity, [ PA ]]Representing the concentration of phenol) is shown in fig. 6.
Example 5
Measuring 800uL carbonic acidSalt buffer solution (0.01 mol/L, pH = 10.0), the above 400uL purified copper doped carbon quantum dots solution (copper doped carbon quantum dots content 7.2 × 10) -5 g/L)、5mM 4-AAP(200μL)、0.5mM H 2 O 2 (200. Mu.L) and 20uL of phenol solution with different concentrations are sequentially added into a 2mL centrifuge tube, the volume is determined, and the mixture is shaken and mixed evenly. After standing at 25 ℃ for 30min, the reaction solution was measured for its ultraviolet absorption spectrum at 505nm as shown in FIG. 7.
Buffer solution of carbonate, H 2 O 2 4-APP, phenol solutions with different concentrations and purified copper-doped quantum dot solutions are mixed to a constant volume of 2mL, the maximum light absorption intensity of the added phenol solutions with different concentrations is used as a vertical coordinate, the concentration of phenol is used as a horizontal coordinate, an ultraviolet absorption spectrum curve equation is established, and the ultraviolet absorption spectrum curve equation Y =0.596 multiplied by 10 is obtained -2 [PA]+0.01955 (Y represents the ultraviolet absorption intensity, [ PA ]]Representing the concentration of phenol) is shown in fig. 8.
Example 6
Accurately measure 800uL of carbonate buffer solution (0.01 mol/L, pH = 10.0), and 400uL of the above purified copper-doped carbon quantum dot solution (the content of copper-doped carbon quantum dots is 7.2 × 10) -5 g/L)、5mM 4-AAP(200μL)、0.5mM H 2 O 2 (200. Mu.L) and 20uL of phenol solution with different concentrations are sequentially added into a 2mL centrifuge tube, the volume is determined, and the mixture is shaken and mixed evenly. Standing at 25 deg.C for 30min, and observing color change as shown in FIG. 9.
Comparative example 1
The isomers of p-phenol, i.e., o-nitrophenol, p-nitrophenol, 3-aminophenol, o-aminophenol and N-acetylphenol, are identified. Accurately measuring 800uL of carbonate buffer solution (0.01 mol/L, pH = 10.0), and 400uL of the purified copper-doped carbon quantum dot solution (the content of the copper-doped carbon quantum dots is 7.2 × 10) -5 g/L)、5mM 4-AAP(200μL)、0.5mM H 2 O 2 (200. Mu.L) and 20. Mu.L of different phenol isomer solutions are added into a 2mL centrifuge tube in sequence, the volume is determined, and the mixture is shaken and mixed evenly. Standing for 30min at constant temperature of 25 ℃, wherein the experimental result is shown in figure 10, and the phenol is obviously different from the isomer thereof, so that the method can be considered to be used forAnd (4) visually identifying phenol. In FIG. 10, 1-o-nitrophenol; 2-p-nitrophenol; 3-aminophenol; 4-catechol; 5-ortho-aminophenol; 6-N-acetylphenol; 7-phenol.
Comparative example 2
In order to study the selectivity of the copper-doped carbon quantum dots to phenol, the response of potassium thiocyanate, nicotinic acid, cys, GSH, serine, histidine, phenol and other substances to the copper-doped carbon quantum dots was examined, and 800uL of a carbonate buffer solution (0.01 mol/L, pH = 10.0) and 400uL of the purified copper-doped carbon quantum dot solution (the content of the copper-doped carbon quantum dots was 7.2 × 10) were accurately measured -5 g/L)、5mM 4-AAP(200μL)、0.5mM H 2 O 2 (200. Mu.L) and 20. Mu.L of the above solutions were added to a 2mL centrifuge tube in sequence, the volume was determined, and the mixture was shaken and mixed. The solution was left standing at a constant temperature of 25 ℃ for 30min, and the experimental results are shown in FIG. 11, and it can be seen that the solution except phenol did not develop color obviously. In FIG. 11, potassium 1-thiocyanate; 2-nicotinic acid; 3-cysteine; 4-glutathione; 5-serine; 6-histidine; 7-phenol.
The result shows that the copper-doped carbon quantum dot has good selectivity to phenol, and the test is carried out three times in each parallel experiment to ensure the accuracy of data.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are all within the protection scope of the present invention.
It should be noted that the technical features described in the above embodiments can be combined in any suitable manner, and the invention is not further described in various possible combinations.
In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present invention.

Claims (1)

1. A method for determining phenol concentration using a copper-doped carbon quantum dot, the method comprising:
(1) Mixing phenol and a blank solution to be tested to obtain a solution to be tested; wherein the blank solution to be tested consists of carbonate buffer solution and H 2 O 2 4-aminoantipyrine and copper-doped carbon quantum dots;
(2) Respectively measuring the maximum fluorescence intensity of a blank solution to be measured and a solution to be measured;
(3) Establishing a fluorescence emission spectrum curve equation by taking the ratio of the maximum fluorescence intensity of the solution to be detected to the maximum fluorescence intensity of the blank solution to be detected as a vertical coordinate and the concentration of phenol as a horizontal coordinate;
(4) Measuring the maximum fluorescence intensity of the phenol, and then calculating according to a fluorescence emission spectrum curve equation to obtain the concentration of the phenol;
the preparation method of the copper-doped carbon quantum dot comprises the following steps: mixing ascorbic acid, 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride, copper acetate and water, and carrying out hydrothermal reaction to obtain the copper-doped carbon quantum dot;
wherein, relative to 1L of water, the dosage of the ascorbic acid is 0.03-0.05mol, the dosage of the 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride is 2.5-2.7mol, and the dosage of the copper acetate is 2.3-2.5mol;
the conditions of the hydrothermal reaction include: the temperature is 200-240 ℃; the time is 7-9h;
the mixing time is 20-40min.
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CN110607175A (en) * 2019-09-26 2019-12-24 安徽师范大学 Copper-doped carbon quantum dot, preparation method thereof and application of copper-doped carbon quantum dot as probe in hydrogen peroxide detection
CN110618119A (en) * 2019-09-26 2019-12-27 安徽师范大学 Method for detecting metronidazole content by using copper-doped carbon quantum dots

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CN110607175A (en) * 2019-09-26 2019-12-24 安徽师范大学 Copper-doped carbon quantum dot, preparation method thereof and application of copper-doped carbon quantum dot as probe in hydrogen peroxide detection
CN110618119A (en) * 2019-09-26 2019-12-27 安徽师范大学 Method for detecting metronidazole content by using copper-doped carbon quantum dots

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