CN112174111A - Preparation method and application of near-infrared light-emitting carbon dots with p-phenylenediamine as carbon source - Google Patents
Preparation method and application of near-infrared light-emitting carbon dots with p-phenylenediamine as carbon source Download PDFInfo
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Abstract
The invention discloses a preparation method and application of a near-infrared luminescent carbon dot taking p-phenylenediamine as a carbon source. The preparation method of the near-infrared luminescent carbon dot takes p-phenylenediamine as a carbon source and water as a dispersion system, and synthesizes carbon dot solution under the microwave heating condition in a hydrochloric acid medium. After the carbon dot solution reacts with the cefradine solution with different concentrations, the fluorescence intensity value of the fluorescent carbon dot solution and the concentration of the cefradine show good linear relation deltaI F =3.01×106 c+6.486 method for detecting concentration of cephradine in solutionIn the range of 0.2X 10‑6~1.0×10‑3mol L‑1. The method has simple process, can quickly prepare the fluorescent carbon dots, and can accurately determine the concentration of the cefradine in the solution.
Description
Technical Field
The invention belongs to the technical field of chemical application. More particularly, relates to a preparation method of a near-infrared luminescent carbon dot using p-phenylenediamine as a carbon source and application thereof in cefradine detection.
Background
Near infrared luminescent carbon dots (NIR-CDs) are novel fluorescent luminescent nano materials, the carbon dots are spherical particles, and the chemical components mainly comprise C, H, O and N. The near-infrared luminescent carbon dots have many excellent properties: such as: the nano-particle has the advantages of high luminous efficiency, good stability, rich raw materials, small particle size, low molecular weight, good biocompatibility, low toxicity, rich groups on the surface, easy combination with molecules such as medicines and the like, and is a good biological medicine carrier.
Cephradine (CEPS), also known as Cephalosporin (CER), has the molecular formula C16H19N3O4S, molecular weight 349.41, white powder, slightly smelly. Has important significance for detecting the content of the cefradine in the nature. The detection method of cefradine mainly comprises high performance liquid chromatography, fluorescence spectrophotometry, nitroprusside sodium spectrophotometry and spectral spectrophotometry. Wherein, the fluorescence spectrophotometry is simple and convenient, the price of the instrument and equipment is relatively low, the detection is rapid, and the detection sensitivity is high.
In the prior art, the prepared carbon dots still have some defects. Most of carbon dot light emitting areas are concentrated in a short-wave area of blue light, and wavelength regulation is difficult to realize. There is still much room for exploring how to more effectively obtain carbon spots with emission wavelengths in the long wavelength region. Generally, in the biological application, a red light or near infrared light-emitting carbon dot material is needed, because the red light material not only has strong penetrating ability to biological tissues, but also can greatly reduce the background fluorescence of tissue proteins. Therefore, how to obtain a carbon dot that emits light in a long wavelength region with high efficiency has been an urgent technical problem to be solved in recent years.
Disclosure of Invention
The invention mainly aims to overcome the defects of the prior art and provides a preparation method of a near-infrared luminescent carbon dot using p-phenylenediamine as a carbon source.
The invention also aims to provide the application of the near-infrared luminescent carbon dot in the detection of the cefradine.
The invention achieves the above object by the following technical scheme.
The invention discloses a preparation method of a near-infrared luminescent carbon dot with p-phenylenediamine as a carbon source, which comprises the following steps:
the method comprises the following steps: mixing a p-phenylenediamine solution with the concentration of 0.02mol/L and a hydrochloric acid solution with the concentration of 0.2mol/L to obtain a mixed solution;
step two: synthesizing the mixed solution under a microwave condition to obtain a carbon dot crude solution;
step three: and centrifuging the carbon dot crude solution to obtain a carbon dot solution.
Therefore, the invention synthesizes the carbon dot solution by taking p-phenylenediamine as a carbon source and water as a dispersion system under the microwave heating condition in a hydrochloric acid medium. The carbon dot solution synthesized by the invention has the characteristic of near red fluorescence, the maximum fluorescence emission wavelength of the carbon dot solution is 689 nm, the penetration capacity to biological tissues is strong under the emission wavelength, and the background fluorescence of tissue protein can be greatly weakened. Therefore, the invention provides a carbon dot material capable of emitting light in a long wavelength region, and solves the technical problem that the wavelength is difficult to regulate to a near-infrared light emitting region in the prior art.
Preferably, the concentration ratio of the p-phenylenediamine solution to the hydrochloric acid solution in the first step is 0.05-0.2: 1.
more preferably, in the first step, the concentration ratio of the p-phenylenediamine solution to the hydrochloric acid solution is 0.1, and the ratio of the solution volume ratio of 1: 1 respectively transferring a p-phenylenediamine solution and a hydrochloric acid solution.
Preferably, the microwave condition in the second step is to heat the mixed solution in a microwave oven, and the microwave power is set to be 140-280W.
More preferably, the time of the heat treatment is 45 minutes.
Preferably, the centrifugation treatment in the third step is to place the carbon dot crude solution in a centrifuge tube for high-speed centrifugation, wherein the centrifugation speed is 12000 r/min, and the centrifugation time is 10 min. And taking the supernatant to obtain the carbon dot solution. Storing at 4 deg.C.
Preferably, the average particle size of the carbon dots in the carbon dot solution is 4.0 nm.
Preferably, the carbon dot solution has a fluorescent characteristic, the maximum excitation wavelength is 297-302 nm, and the maximum emission wavelength is 687-691 nm.
In addition, the application of the near-infrared luminescent carbon dot taking p-phenylenediamine as a carbon source in cefradine detection is provided.
Preferably, the above application comprises the following steps:
a. detecting the fluorescence intensity of the carbon dot solution and a system obtained after the carbon dot solution reacts with the cefradine with different concentrations;
b. calculating the linear relation between the fluorescence intensity value and the concentration of the cefradine according to the fluorescence intensity value of the reaction of the fluorescent carbon dot solution and the solutions with different concentrations of the cefradine;
c. detecting the fluorescence intensity of the cefradine in the sample to be detected, and calculating the content of the cefradine in the sample to be detected according to the linear relation.
Preferably, the concentration range of the detection solution of cefradine used in the above method is 0.2 × 10-6 ~1.0×10-3 mol L-1。
The invention has the following beneficial effects:
the preparation method of the near-infrared luminescent carbon dot takes p-phenylenediamine as a carbon source and water as a dispersion system, and synthesizes carbon dot solution under the microwave heating condition in a hydrochloric acid medium. The method has the characteristics of cheap and easily-obtained raw materials, low cost, simple preparation process and wide detection range. Has potential application value in the detection and imaging field of the cefradine.
Drawings
FIG. 1 is a fluorescence spectrum of a carbon dot solution prepared in example 1 of the present invention;
FIG. 2 is a TEM image of a carbon dot solution prepared in example 1 of the present invention and a particle size distribution thereof;
FIG. 3 is a fluorescence spectrum of a carbon dot solution prepared in example 1 of the present invention for detecting different concentrations of cephradine;
FIG. 4 is a graph of the fluorescence intensity correlation ratio of the carbon dot solution prepared in example 2 of the present invention plotted linearly against the concentration of cephradine.
Detailed Description
The invention is further described with reference to the drawings and the following detailed description, which are not intended to limit the invention in any way. Reagents, methods and apparatus used in the present invention are conventional in the art unless otherwise indicated.
Unless otherwise indicated, reagents and materials used in the present invention are commercially available.
Example 1
(1) Preparation of carbon dots
Mixing 0.02mol/L p-phenylenediamine solution prepared by secondary water and 0.2mol/L hydrochloric acid solution according to a certain proportion, placing the mixed solution in a microwave oven to react for 45 min under the microwave power of 280W, and cooling to room temperature after the reaction is finished to obtain a carbon dot crude solution. The carbon dot crude solution is firstly centrifuged at 12000 rpm for 10 minutes, and the supernatant is taken, namely the carbon dot solution. As shown in FIG. 1, the maximum excitation wavelength is 300 nm and the maximum emission wavelength is 689 nm. And the morphology of the carbon points and the like are subjected to AFM characterization, and as shown in figure 2, the synthesized carbon points have good dispersibility. The results of the particle size distribution are shown in FIG. 3, and the average particle size of the carbon dots is 4.0 nm.
(2) Optimization of preparation conditions of carbon dots
The influence of the fluorescence intensity of the synthesized carbon dot solution was examined. The experiment optimizes the synthesis conditions of the carbon dots by adopting a single-factor variable control method. The method is respectively researched from four aspects of the concentration ratio of raw materials, the synthesis microwave power, the synthesis time and the total volume of the raw materials in the carbon point synthesis.
The concentration ratios of p-phenylenediamine solution and hydrochloric acid solution were 0.01, 0.03, 0.1, 0.3, and 0.75, respectively, which had the effect on the fluorescence intensity of the synthesized carbon dot solution, and the fluorescence intensity of the carbon dot system was the strongest when the concentration ratio of p-phenylenediamine and hydrochloric acid was 0.1. Therefore, the final preferred concentration ratio of p-phenylenediamine to hydrochloric acid is 0.1.
The synthetic microwave power of the carbon dots has certain influence on the fluorescence intensity of a carbon dot system, and the influence of the reaction microwave power on the fluorescence intensity of the synthetic carbon dot solution when the reaction microwave power is respectively low fire (140W), medium fire (280W), medium fire (420W), medium fire (560W) and high fire (700W) is researched. When the synthetic microwave power is medium-low fire, the fluorescence intensity of the carbon dot system is strongest, so the finally preferred synthetic microwave power is medium-low fire (280W).
The synthesis time of the carbon dots also has a certain influence on the fluorescence intensity of the carbon dot solution, and influences on the fluorescence intensity of the synthesized carbon dots when the synthesis time is 35 min, 40 min, 45 min, 50 min, 55 min and 60 min respectively are discussed. When the synthesis time is 45 min, the fluorescence intensity of the carbon dot solution is strongest, and therefore, the synthesis time is preferably 45 min.
The total volume of the synthesis raw materials for the carbon dots also has a certain influence on the fluorescence intensity of the carbon dot solution, and the influence on the fluorescence intensity of the synthesized carbon dots when the total volume of the synthesis raw materials is 5.0 mL, 10.0 mL, 20.0 mL, 30.0 mL, and 50.0 mL, respectively, was examined. When the total volume of the synthesis raw materials is 10.0 mL, the fluorescence intensity of the carbon dot solution is the strongest, and therefore the total volume of the synthesis raw materials is preferably 10.0 mL.
(3) Optimization of carbon point and cefradine reaction conditions
In order to obtain the optimal experimental conditions of the interaction between carbon points and cefradine, a single-factor control variable method is adopted to respectively explore from four aspects of reaction pH value, reaction temperature, carbon point concentration in the reaction and reaction time, so that the sensitivity of the detection method is highest.
Effect of temperature T on interaction of carbon dots with cephradine: the reaction temperature is in the range of 4-65 ℃, the change value of the fluorescence intensity of the carbon dot system is gradually reduced along with the rise of the temperature, and the change of the fluorescence intensity of the system is maximum at 4 ℃, so the optimal response temperature of the reaction is 4 ℃. The temperature of the final reaction was controlled to 4 ℃ in consideration of the fact that the temperature control of the reaction system was not convenient below 4 ℃.
Influence of the addition of the carbon dot solution on the interaction of carbon dots and cephradine: the fluorescence intensity of the carbon dot system with the total volume of 2.0 mL is firstly enhanced and then weakened with the increase of the addition amount of the carbon dot solution, and when the addition amount of the carbon dot solution is 1.0 mL, the fluorescence intensity of the system is changed the most with the addition of 0.2 mL of BR buffer solution, 0.6 mL of secondary aqueous solution and 0.2 mL of cephradine solution, so the addition amount of the carbon dot solution is preferably 1.0 mL.
Effect of reaction time on interaction of carbon point with cephradine: with the increase of the reaction time, the fluorescence intensity of the carbon dot system is firstly increased and then gradually weakened, and when the reaction is carried out for 40 min, the fluorescence intensity of the system is changed maximally, so the optimal reaction time is 40 min.
The influence of the pH of the system on the carbon point detection of cephradine: the pH values of the systems were set to 1.81, 2.48, 3.57, 4.53, 5.35, 6.28, 7.06, 8.08, 9.56, 10.74 and 11.51, respectively, and 1.0 mL of the carbon dot solution prepared under the optimum conditions, 0.2 mL of the BR buffer solution having a different pH, and 0.2 mL of the 2.0X 10 solution were added to 11 and 2 mL centrifuge tubes-3 mol L-1The cefradine solution and 0.6 mL of secondary water are added to reach the constant volume of 2.0 mL, and after the solution is uniformly mixed, the reaction is carried out for 40 min at the temperature of 4 ℃. When the change in the fluorescence intensity of the system was measured, the change in the fluorescence intensity of the system was the greatest at pH 3.57, and the optimum pH for the reaction was 3.57.
(4) Detection parameters of cefradine solution with different concentrations on fluorescence intensity of carbon dot system
Influence of different concentrations of cephradine solutions on the fluorescence intensity of the carbon dot system. Is provided with a concentration of 2.0 x 10-3 mol L-1The cefradine standard solution is used as mother solution and is sequentially diluted into the concentration of 2.0 multiplied by 10-7、 2.0×10-6、 1.0×10-5、 2.0×10-5、 3.0×10-5、5.0×10-5、 8.0×10-5 、2.0×10-4、 1.0×10-3The mol/L of the standard solution of cephradine is shown in FIG. 3, wherein 1 to 8 indicate that the concentrations of the added cephradine solution are: 0.0, 2.0X 10-7、1.0×10-5 、2.0×10-5、3.0×10-5、5.0×10-5 、8.0×10-5、1.0×10-3 mol/L。
Example 2
Carbon point detection parameters of cefradine concentration:
add 1.0 mL of the best seen in example 1 to a 2.0 mL centrifuge tubeThe carbon dot solution prepared under the above conditions was added with 0.2 mL of Britton-Robinson (BR) buffer solution, and 0.2 mL of each buffer solution was added to the solution at a concentration of from 0.2X 10-6 mol L-1Increase to 1.0X 10-3 mol L-1The solution of cefradine is added with 0.6 mL of secondary water to reach 2.0 mL of constant volume, and after the solution is mixed evenly, the reaction is carried out for 40 min at the temperature of 4 ℃. Under the same experimental conditions, a blank was set up with secondary water instead of cephradine. Setting an excitation wavelength of 300 nm, an excitation slit width of 15 nm and an emission slit width of 5 nm, measuring the fluorescence intensity of the system by a fluorescence spectrophotometer to obtain the fluorescence spectrograms of an experimental sample and a blank sample, and comparing the fluorescence intensity values of the carbon dot system with or without adding cefradine. The results are shown in FIG. 4, and the fluorescence intensity value of the fluorescent carbon dot solution and the concentration of cefradine show good linear relation, and the linear regression equation is deltaI F =3.01×106 c+6.486, wherein ΔI F The difference between the fluorescence intensity value without adding cephradine and the fluorescence intensity value after adding cephradine,cthe concentration of cephradine in the solution was detected to be in the range of 0.2X 10-6 mol L-1-1.0×10-3 mol L-1The detection limit is as follows: 0.084X 10-6 mol L-1. Three sets of actual samples were determined from the linear relationship and the results are shown in table 1. As can be seen, the measured recovery rate is 100.63% -102.44%. The measured recovery rate is more than 99 percent, which shows that the method has better practical application value.
Finally, it should be noted that the above embodiments are only used for illustrating the technical solutions of the present invention and not for limiting the protection scope of the present invention, and although the present invention is described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions can be made on the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention.
Claims (10)
1. A method for preparing a near-infrared luminescent carbon dot by taking p-phenylenediamine as a carbon source comprises the following steps:
the method comprises the following steps: mixing a p-phenylenediamine solution with the concentration of 0.02mol/L and a hydrochloric acid solution with the concentration of 0.2mol/L to obtain a mixed solution;
step two: synthesizing the mixed solution under a microwave condition to obtain a carbon dot crude solution;
step three: and centrifuging the carbon dot crude solution to obtain a carbon dot solution.
2. The method for preparing a near-infrared luminescent carbon dot by using p-phenylenediamine as a carbon source according to claim 1, wherein the method comprises the following steps: step one, the concentration ratio of the p-phenylenediamine solution to the hydrochloric acid solution is 0.05-0.2: 1.
3. the method for preparing a near-infrared luminescent carbon dot by using p-phenylenediamine as a carbon source according to claim 1, wherein the method comprises the following steps: in the first step, the concentration ratio of the p-phenylenediamine solution to the hydrochloric acid solution is 0.1.
4. The method for preparing a near-infrared luminescent carbon dot by using p-phenylenediamine as a carbon source according to claim 1, wherein the method comprises the following steps: and step two, the microwave condition is that the mixed solution is placed in a microwave oven for heating treatment, the microwave power is set to be 280W, and the heating treatment time is 45 minutes.
5. The method for preparing a near-infrared luminescent carbon dot by using p-phenylenediamine as a carbon source according to claim 1, wherein the method comprises the following steps: and step three, the centrifugation treatment is to place the carbon dot crude solution in a centrifuge tube for high-speed centrifugation separation, wherein the centrifugation speed is 12000 r/min, the centrifugation time is 10 min, and supernatant is taken to obtain the carbon dot solution.
6. The method for preparing a near-infrared luminescent carbon dot by using p-phenylenediamine as a carbon source according to claim 1, wherein the method comprises the following steps: the average grain diameter of the carbon dots in the carbon dot solution is 4.0 nm.
7. The method for preparing a near-infrared luminescent carbon dot by using p-phenylenediamine as a carbon source according to claim 1, wherein the method comprises the following steps: the carbon dot solution has a fluorescence characteristic, the maximum excitation wavelength is 297-302 nm, and the maximum emission wavelength is 687-691 nm.
8. Use of the near-infrared luminescent carbon dot according to any one of claims 1 to 7, wherein the carbon dot is formed by p-phenylenediamine as a carbon source, for detecting cephradine.
9. The application of the near-infrared luminescent carbon dot taking p-phenylenediamine as a carbon source in the detection of cephradine as claimed in claim 8, wherein the method comprises the following steps:
a. detecting the fluorescence intensity of the carbon dot solution and a system obtained after the carbon dot solution reacts with the cefradine with different concentrations;
b. calculating the linear relation between the fluorescence intensity value and the concentration of the cefradine according to the fluorescence intensity value of the reaction of the fluorescent carbon dot solution and the solutions with different concentrations of the cefradine;
c. detecting the fluorescence intensity of the cefradine in the sample to be detected, and calculating the content of the cefradine in the sample to be detected according to the linear relation.
10. The use of the near-infrared luminescent carbon spot with p-phenylenediamine as a carbon source for detecting cephradine as claimed in claim 8, wherein the concentration range of cephradine in the sample to be detected in step c is 0.2 x 10-6 ~1.0×10-3 mol L-1。
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Application publication date: 20210105 |