CN110982520A - Boron-nitrogen co-doped carbon quantum dot and preparation and application thereof - Google Patents
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Abstract
The invention relates to a boron-nitrogen co-doped carbon quantum dot, which is solid powder of the boron-nitrogen co-doped carbon quantum dot obtained by dissolving o-phenylenediamine as a carbon source and a nitrogen source and boric acid as a boron source dopant in water to perform microwave-assisted hydrothermal reaction and purifying a reaction product. The particle size of the boron-nitrogen co-doped carbon quantum dot prepared by the method is less than 10nm, the boron-nitrogen co-doped carbon quantum dot can emit 560nm long-wavelength yellow fluorescence under excitation, the fluorescence quantum yield is high, the excitation independence, the low toxicity and the good biocompatibility are realized, and the boron-nitrogen co-doped carbon quantum dot can be used as a fluorescence probe to be applied to cell imaging.
Description
Technical Field
The invention belongs to the technical field of carbon quantum dot preparation, and relates to a boron-nitrogen co-doping-based carbon quantum dot, a preparation method of the carbon quantum dot, and application of the carbon quantum dot in cell imaging.
Background
The carbon quantum dot is a carbon nanoparticle having excellent photoluminescence properties. The shape of the fluorescent nano material is similar to that of a spherical monodisperse fluorescent carbon nano material, and the particle size is generally less than 10 nm. The carbon quantum dots not only have the advantages of adjustable emission wavelength, photobleaching resistance and the like of the traditional semiconductor quantum dots, but also have the advantages of low toxicity, good biocompatibility, good water solubility, wide raw material source, easy functional modification and the like, and have good application prospect and development potential in the aspects of tumor diagnosis, cell marking, drug delivery and the like.
However, carbon quantum dots currently used for cell imaging all emit blue light under ultraviolet light excitation. The blue light carbon quantum dots have the defects of Raman scattering and Rayleigh scattering interference because the Stokes shift of the blue light carbon quantum dots is small. Meanwhile, biological tissues composed of carbohydrates emit blue light by themselves, which interferes with the monitoring of cells by blue light carbon quantum dots, and limits the further application of carbon quantum dots in biological imaging (Shen, P. and Xia, Y. Synthesis-modification integration: one-step architecture of boron acid functionalized carbon dots for fluorescent coating sensing).Anal Chem. 2014, 86, 5323-5329.;Shen, C.,Wang, J., Cao, Y. and Lu, Y. Facile access to B-doped solid-state fluorescentcarbon dots toward light emitting devices and cell imaging agents.Journal of Materials Chemistry C.2015, 3, 6668-6675.)。
Therefore, the preparation of carbon quantum dots with large stokes shift for long wavelength emission such as yellow and red light is a fundamental approach to solve the problems in the field of cell imaging.
Disclosure of Invention
The invention aims to overcome the defects of short emission wavelength and low fluorescence quantum yield of the existing carbon quantum dot, and provides a boron-nitrogen co-doped carbon quantum dot.
The invention also aims to provide a preparation method of the boron-nitrogen co-doped carbon quantum dot with short preparation period.
The invention also provides an application of the boron-nitrogen co-doped carbon quantum dot in cell marker imaging.
Based on the purpose, the boron-nitrogen co-doped carbon quantum dot is boron-nitrogen co-doped carbon quantum dot solid powder obtained by dissolving o-phenylenediamine as a carbon source and a nitrogen source and boric acid as a boron source dopant in water to perform microwave-assisted hydrothermal reaction and purifying a reaction product.
The particle size of the boron-nitrogen co-doped carbon quantum dot prepared by the method is less than 10nm, and the boron-nitrogen co-doped carbon quantum dot can emit 560nm yellow fluorescence under excitation.
Furthermore, the invention provides a preparation method of the boron-nitrogen co-doped carbon quantum dot, which is characterized by dissolving o-phenylenediamine and boric acid in water to obtain a precursor solution, placing the precursor solution in a closed device, carrying out microwave-assisted hydrothermal reaction at 180-220 ℃, filtering, dialyzing, purifying and drying a reaction product to obtain purified boron-nitrogen co-doped carbon quantum dot solid powder.
Specifically, in the preparation method, the molar ratio of the o-phenylenediamine to the boric acid is 1: 1-2.
More specifically, the microwave-assisted hydrothermal reaction time is preferably 5-70 min.
The invention preferably uses a 0.22 μm microporous filter membrane to filter the hydrothermal reaction product to separate and remove large particle impurities.
Furthermore, the invention adopts a dialysis bag with the molecular weight cutoff of 1000Da to dialyze the filtered filtrate, and then the unreacted or by-product micromolecules are removed by purification. The dialysis time is not less than 48h, and water is changed every 12 h.
And drying the dialyzed solution to obtain the boron-nitrogen co-doped carbon quantum dot solid powder.
Preferably, the dialyzed and purified carbon quantum dots are subjected to freeze drying under a vacuum condition to obtain boron-nitrogen co-doped carbon quantum dots.
More specifically, the vacuum degree of the freeze drying under the vacuum condition is 20Pa, the drying temperature is-80 ℃, and the drying time is 12 h.
The boron-nitrogen co-doped carbon quantum dot prepared by the method has the fluorescence quantum yield of more than 10%.
The boron-nitrogen co-doped carbon quantum dot prepared by the method can be used as a fluorescent probe.
Furthermore, the boron-nitrogen co-doped carbon quantum dot prepared by the invention can be used as a fluorescent probe and applied to cell imaging.
The boron-nitrogen co-doped carbon quantum dot prepared by the method is used as a fluorescent probe to be incubated with a HeLa cell of cervical cancer, and a clear carbon quantum dot marking cell image is observed under a laser confocal microscope.
In the cell image, after the boron-nitrogen co-doped carbon quantum dots are treated, the cells have no obvious morphological damage, which indicates that the boron-nitrogen co-doped carbon quantum dots have low cytotoxicity and good biocompatibility. Meanwhile, only weak fluorescence or no fluorescence is observed at the cell nucleus position in the center of the cell, and the cytoplasm area around the cell nucleus displays bright yellow fluorescence, so that the boron-nitrogen co-doped carbon quantum dot is proved to be suitable for being used as a fluorescent probe for cell imaging.
According to the invention, o-phenylenediamine is used as a carbon source and a nitrogen source, boric acid is used as a boron source, and the boron-nitrogen co-doped carbon quantum dot solid powder is rapidly prepared by microwave-assisted hydrothermal reaction. The prepared boron-nitrogen co-doped carbon quantum dot not only has good water solubility, but also has excellent fluorescence characteristic, can emit long-wavelength yellow light, has the fluorescence quantum yield of more than 10%, and has obvious superiority compared with the carbon quantum dot emitted at short wavelength.
The preparation method of the boron-nitrogen co-doped carbon quantum dot has the advantages of simple process, short reaction time, greenness, no pollution, good experimental repeatability, uniform size of the prepared boron-nitrogen co-doped carbon quantum dot, high quantum yield and good biocompatibility.
The invention can provide a long-wavelength emission water-soluble nano fluorescent probe with excitation independence, bleaching resistance, low toxicity and good biocompatibility for the field of biological medicine, has a great application prospect in the field of cell imaging, and provides corresponding theoretical data for early diagnosis and accurate treatment of tumors.
Drawings
Fig. 1 is a transmission electron microscope image of boron-nitrogen co-doped carbon quantum dots prepared in example 1.
Fig. 2 is a full spectrum of X-ray electron spectroscopy analysis of boron-nitrogen co-doped carbon quantum dots prepared in example 1.
FIG. 3 is a fluorescence emission spectrum of boron-nitrogen co-doped carbon quantum dot aqueous solution at different excitation wavelengths.
Fig. 4 shows the ultraviolet-visible absorption spectrum, excitation spectrum and emission spectrum of the boron-nitrogen co-doped carbon quantum dot.
FIG. 5 is a graph of light intensity changes of boron-nitrogen co-doped carbon quantum dot aqueous solution under different illumination times.
Fig. 6 shows the toxicity result of boron-nitrogen co-doped carbon quantum dots on cervical cancer HeLa cells.
Fig. 7 is an imaging result of the boron-nitrogen co-doped carbon quantum dots prepared in example 1 on a cervical cancer HeLa cell.
Detailed Description
The present invention will be described in further detail with reference to specific examples and test examples. The following examples are only preferred embodiments of the present invention and are not intended to limit the present invention in any way. Various modifications and alterations to this invention will become apparent to those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Example 1.
0.27g (2.5mmol) of o-phenylenediamine and 0.15g (2.4mmol) of boric acid are weighed, added into 10mL of ultrapure water, and stirred at room temperature until completely dissolved to obtain a precursor solution.
And sealing the precursor solution in a glass tube for a microwave synthesizer, heating the precursor solution to 200 ℃ in microwaves with the working pressure of 30bar, carrying out hydrothermal reaction for 10min, and cooling the precursor solution to room temperature to prepare the brown solution.
The brown solution was filtered through a 0.22 μm microfiltration membrane to remove large particulate impurities and obtain a light brown solution. And putting the solution into a dialysis bag with the molecular weight cutoff of 1000Da for dialysis for not less than 48 hours, and removing unreacted or by-product micromolecules to obtain a purified solution. During the period, water is changed every 12 h.
And collecting the purified solution in the dialysis bag, and drying to obtain boron-nitrogen co-doped carbon quantum dot solid powder.
Fig. 1 provides a transmission electron microscopic image of the boron-nitrogen co-doped carbon quantum dot prepared above. According to the particle size statistical illustration in the figure 1 and the figure, the prepared boron-nitrogen co-doped carbon quantum dots are spherical zero-dimensional carbon nano materials with the size less than 10nm, the diameter distribution range is 2.0-9.0 nm, the average particle size is 5.5nm, the dispersibility is good, and no obvious agglomeration exists.
Fig. 2 is a full spectrum of the X-ray electron spectrum analysis of the boron-nitrogen co-doped carbon quantum dot prepared in the above way. The binding energies of B1 s, C1 s, N1 s and O1 s at 193.08, 285.08, 400.08 and 532.08eV in the graph respectively correspond, and the relative contents thereof are 24.12%, 28.25%, 5.68% and 41.96% respectively, demonstrating that the boron element and the nitrogen element are co-doped in the carbon quantum dot.
Fig. 3 shows fluorescence emission spectrograms of the aqueous solution for preparing boron-nitrogen co-doped carbon quantum dots under different excitation wavelengths. It can be seen from the figure that the intensity of the emission peak increases and then decreases as the excitation wavelength increases, and the emission intensity reaches a maximum at an excitation wavelength of 420 nm. And the emission peak value does not change along with the change of the excitation wavelength, and the emission peak position is always kept at 560nm, which shows that the boron-nitrogen co-doped carbon quantum dot has excitation independence.
Fig. 4 shows an ultraviolet-visible absorption spectrum, an excitation spectrum and an emission spectrum of the boron-nitrogen co-doped carbon quantum dot prepared in the above way. According to the difference value of the emission peak value and the excitation peak value in the graph, the obtained boron-nitrogen co-doped carbon quantum dot has higher Stokes shift of 162nm and has wide application potential in the field of cell imaging.
Fig. 5 is a graph of light intensity changes of the aqueous solution for preparing boron-nitrogen co-doped carbon quantum dots under different illumination times. After the continuous ultraviolet excitation is carried out for 60min under the ultraviolet light with the wavelength of 420nm, no obvious photobleaching is found, which indicates that the boron-nitrogen co-doped carbon quantum dot has high light stability.
And taking the cervical cancer HeLa cell as a research object, and performing cytotoxicity analysis test on the boron-nitrogen co-doped carbon quantum dot by adopting a CCK-8 method.
Inoculating HeLa cells of cervical cancer into a culture flask, and culturing at 37 deg.C and 5% CO2Culturing in an incubator until the cell fusion degree reaches 80-90%, digesting with pancreatin, diluting with 1640 culture medium, centrifuging at 1000rpm/min for 5min, removing supernatant, dispersing cells in 1640 culture medium, counting cells, and adjusting cell suspension density to 2.5 × 104cells/mL, 0.1mL per well in 96 well cell culture plates, cultured for 24 h.
Then, the culture solution was replaced with a culture solution containing boron-nitrogen CO-doped carbon quantum dots with concentrations of 0, 10, 20, 30, 40, 50 and 80 μ g/mL, 6 multiple wells were made in parallel in the presence of 5% CO2Continuously culturing for 24h at 37 ℃ in the incubator, discarding the boron-nitrogen co-doped carbon quantum dot culture solution, washing with sterile PBS buffer solution with pH =7.4 for 3 times, adding 100 mu L of 1640 culture solution containing 10% CCK-8 into each hole, continuously culturing for 1h, measuring OD value at 450nm by using an enzyme labeling instrument, and analyzing the survival rate of the HeLa cells of the cervical cancer.
As can be seen from the toxicity test results in FIG. 6, the survival rate of the HeLa cells of the cervical cancer cells is not significantly different when the cells are incubated in the culture solution containing the boron-nitrogen co-doped carbon quantum dots with different concentrations for 24 h. The fact that the cells are not toxic even if the cervical cancer HeLa cells are incubated in the boron-nitrogen co-doped carbon quantum dot culture medium with the concentration of 80 mug/mL for 24 hours shows that the boron-nitrogen co-doped carbon quantum dots have good biocompatibility and low toxicity.
Will be 1 × 105Spreading HeLa cells in a confocal culture dish at 37 deg.C and 5% CO2The culture was carried out overnight in an incubator. And after the cells adhere to the wall, adding a culture solution containing 50 mu g/mL boron-nitrogen co-doped carbon quantum dots, and incubating for 6 h. Culture for discarding boron-nitrogen-containing co-doped carbon quantum dotsAnd washing the solution with PBS for 3 times to remove residual boron-nitrogen co-doped carbon quantum dots. The method is characterized in that 405nm laser is used as an excitation light source, observation and shooting are carried out under a laser confocal microscope, and 540-580 nm emitted light signals are collected to carry out in-vitro cell imaging.
Fig. 7 shows an optical microscope image of boron-nitrogen co-doped carbon quantum dots entering into a HeLa cell of cervical cancer. The cell image after the boron-nitrogen co-doped carbon quantum dot is treated clearly shows that the boron-nitrogen co-doped carbon quantum dot is easily absorbed by cells and mainly located in cytoplasm, so that the boron-nitrogen co-doped carbon quantum dot can mark the cells, the cells have no obvious morphological damage, and the boron-nitrogen co-doped carbon quantum dot is further proved to have low cytotoxicity and good biocompatibility.
Example 2.
0.27g (2.5mmol) of o-phenylenediamine and 0.15g (2.4mmol) of boric acid are weighed, added into 10mL of ultrapure water, and stirred at room temperature until completely dissolved to obtain a precursor solution.
And sealing the precursor solution in a glass tube for a microwave synthesizer, heating the precursor solution to 220 ℃ in microwaves with the working pressure of 30bar, carrying out hydrothermal reaction for 40min, and cooling the precursor solution to room temperature to prepare the brown solution.
The brown solution was filtered through a 0.22 μm microfiltration membrane to remove large particulate impurities and obtain a light brown solution. And putting the solution into a dialysis bag with the molecular weight cutoff of 1000Da for dialysis for not less than 48 hours, and removing unreacted or by-product micromolecules to obtain a purified solution. During the period, water is changed every 12 h.
And collecting the purified solution in the dialysis bag, and drying to obtain boron-nitrogen co-doped carbon quantum dot solid powder.
Example 3.
0.27g (2.5mmol) of o-phenylenediamine and 0.23g (3.75mmol) of boric acid are weighed, added into 10mL of ultrapure water, and stirred at room temperature until completely dissolved to obtain a precursor solution.
And sealing the precursor solution in a glass tube for a microwave synthesizer, heating the precursor solution to 180 ℃ in microwaves with the working pressure of 30bar, carrying out hydrothermal reaction for 10min, and cooling the precursor solution to room temperature to prepare the brown solution.
The brown solution was filtered through a 0.22 μm microfiltration membrane to remove large particulate impurities and obtain a light brown solution. And putting the solution into a dialysis bag with the molecular weight cutoff of 1000Da for dialysis for not less than 48 hours, and removing unreacted or by-product micromolecules to obtain a purified solution. During the period, water is changed every 12 h.
And collecting the purified solution in the dialysis bag, and drying to obtain boron-nitrogen co-doped carbon quantum dot solid powder.
Example 4.
0.27g (2.5mmol) of o-phenylenediamine and 0.23g (3.75mmol) of boric acid are weighed, added into 10mL of ultrapure water, and stirred at room temperature until completely dissolved to obtain a precursor solution.
And sealing the precursor solution in a glass tube for a microwave synthesizer, heating the precursor solution to 220 ℃ in microwaves with the working pressure of 30bar, carrying out hydrothermal reaction for 5min, and cooling the precursor solution to room temperature to prepare the brown solution.
The brown solution was filtered through a 0.22 μm microfiltration membrane to remove large particulate impurities and obtain a light brown solution. And putting the solution into a dialysis bag with the molecular weight cutoff of 1000Da for dialysis for not less than 48 hours, and removing unreacted or by-product micromolecules to obtain a purified solution. During the period, water is changed every 12 h.
And collecting the purified solution in the dialysis bag, and drying to obtain boron-nitrogen co-doped carbon quantum dot solid powder.
Example 5.
0.27g (2.5mmol) of o-phenylenediamine and 0.30g (4.8mmol) of boric acid are weighed, added into 10mL of ultrapure water, and stirred at room temperature until completely dissolved to obtain a precursor solution.
And sealing the precursor solution in a glass tube for a microwave synthesizer, heating the precursor solution to 220 ℃ in microwaves with the working pressure of 30bar, carrying out hydrothermal reaction for 10min, and cooling the precursor solution to room temperature to prepare the brown solution.
The brown solution was filtered through a 0.22 μm microfiltration membrane to remove large particulate impurities and obtain a light brown solution. And putting the solution into a dialysis bag with the molecular weight cutoff of 1000Da for dialysis for not less than 48 hours, and removing unreacted or by-product micromolecules to obtain a purified solution. During the period, water is changed every 12 h.
And collecting the purified solution in the dialysis bag, and drying to obtain boron-nitrogen co-doped carbon quantum dot solid powder.
Example 6.
0.27g (2.5mmol) of o-phenylenediamine and 0.30g (4.8mmol) of boric acid are weighed, added into 10mL of ultrapure water, and stirred at room temperature until completely dissolved to obtain a precursor solution.
And sealing the precursor solution in a glass tube for a microwave synthesizer, heating the precursor solution to 200 ℃ in microwaves with the working pressure of 30bar, carrying out hydrothermal reaction for 70min, and cooling the precursor solution to room temperature to prepare the brown solution.
The brown solution was filtered through a 0.22 μm microfiltration membrane to remove large particulate impurities and obtain a light brown solution. And putting the solution into a dialysis bag with the molecular weight cutoff of 1000Da for dialysis for not less than 48 hours, and removing unreacted or by-product micromolecules to obtain a purified solution. During the period, water is changed every 12 h.
And collecting the purified solution in the dialysis bag, and drying to obtain boron-nitrogen co-doped carbon quantum dot solid powder.
Claims (10)
1. The boron-nitrogen co-doped carbon quantum dot is prepared by dissolving o-phenylenediamine serving as a carbon source and a nitrogen source and boric acid serving as a boron source dopant in water to perform microwave-assisted hydrothermal reaction, purifying a reaction product to obtain boron-nitrogen co-doped carbon quantum dot solid powder, and exciting the boron-nitrogen co-doped carbon quantum dot to emit 560nm yellow fluorescence.
2. The preparation method of the boron-nitrogen co-doped carbon quantum dot according to claim 1, wherein o-phenylenediamine and boric acid are dissolved in water to obtain a precursor solution, the precursor solution is placed in a closed device and subjected to microwave-assisted hydrothermal reaction at 180-220 ℃, and a reaction product is filtered, dialyzed, purified and dried to obtain purified boron-nitrogen co-doped carbon quantum dot solid powder.
3. The preparation method of the boron-nitrogen co-doped carbon quantum dot according to claim 2, wherein the molar ratio of o-phenylenediamine to boric acid is 1: 1-2.
4. The preparation method of the boron-nitrogen co-doped carbon quantum dot according to claim 2, wherein the microwave-assisted hydrothermal reaction time is 5-70 min.
5. The method for preparing boron-nitrogen co-doped carbon quantum dots according to claim 2, wherein the reaction product is filtered by using a 0.22 μm microporous filter membrane, and then the filtered filtrate is dialyzed by using a dialysis bag with the molecular weight cutoff of 1000 Da.
6. The method for preparing boron-nitrogen co-doped carbon quantum dots according to claim 5, wherein the dialysis time is not less than 48h, and water is changed every 12 h.
7. The method for preparing boron-nitrogen co-doped carbon quantum dots according to claim 2, wherein the dialyzed and purified carbon quantum dots are subjected to freeze drying under a vacuum condition.
8. The method for preparing boron-nitrogen co-doped carbon quantum dots according to claim 7, wherein the vacuum degree of freeze drying under vacuum condition is 20Pa, the drying temperature is-80 ℃, and the drying time is 12 h.
9. The application of the boron-nitrogen co-doped carbon quantum dot as claimed in claim 1 as a fluorescent probe.
10. The use of boron-nitrogen co-doped carbon quantum dots according to claim 1 as fluorescent probes for cell imaging.
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