CN110616071B - Red light doped graphene quantum dot and preparation method thereof - Google Patents
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Abstract
The invention discloses a red light doped graphene quantum dot and a preparation method thereof, wherein the method comprises the following steps: mixing a precursor material with a solvent to obtain a precursor solution; carrying out hydro-thermal synthesis treatment on the precursor solution to obtain a reaction product; and purifying the reaction product to obtain the red light doped graphene quantum dot. The red light doped graphene quantum dot and the preparation method thereof, which are obtained by the embodiment of the invention, have the advantages of high fluorescence intensity and high yield, emit red fluorescence under the irradiation of an ultraviolet lamp, and can be widely applied to the field of biological imaging.
Description
Technical Field
The invention relates to the technical field of material chemistry, in particular to a red light doped graphene quantum dot and a preparation method thereof.
Background
The graphene quantum dot is a quasi-zero-dimensional nano material, and the movement of electrons in the graphene quantum dot in all directions is limited, so that the quantum confinement effect is particularly obvious, and the graphene quantum dot has unique physical and chemical properties, which can bring revolutionary changes to the fields of electronics, photoelectricity and electromagnetism. Compared with the traditional fluorescent material, the fluorescent material has a wider excitation wavelength range and a narrower emission wavelength range, and the light-emitting characteristic is continuously adjustable; the structure is stable, and the corrosion of strong acid and strong alkali is resisted; does not contain toxic metal elements, is green and environment-friendly, has good biocompatibility and the like. The graphene quantum dots have extremely high biocompatibility, fluorescence stability, controllable emission wavelength, wide excitation wavelength range, low biotoxicity, good solubility and the like in optics, so that the graphene quantum dots become a good biological imaging probe. Compared with graphene, the graphene quantum dots can be used widely in biosensing, bioimaging and biological drug delivery.
In the field of biomedicine, fluorescence is often used for marking an object, and compared with a traditional fluorescent reagent which is easy to fail due to long excitation time, the graphene quantum dots can emit stable fluorescence for a long time, and people can obtain light with various colors by changing the size of the graphene quantum dots, so that the graphene quantum dots have a wide application prospect in biological imaging. On the other hand, as the graphene quantum dots have the characteristics of large body surface area, good water solubility, low biotoxicity and the like, the drugs can be fixed on the graphene quantum dots through a physical or chemical method to form drug delivery carriers, the release effect of the drugs is enhanced through chemical modification, and a new idea is provided for improvement of curative effect and research and development of antitumor drugs.
Most of graphene quantum dots in the current research emit blue light, green light or yellow light, wherein red light has the advantages of strong penetrating power, low excitation energy, small background fluorescence interference and the like, so that the fluorescent material emitting red light has many advantages in the field of biological imaging. Therefore, the red fluorescence luminescent graphene quantum dot material has a very wide prospect in the field of biological imaging. However, the types and the number of the red-doped graphene quantum dots are quite limited at present.
Disclosure of Invention
The embodiment of the invention provides a red light doped graphene quantum dot and a preparation method thereof, which can emit red fluorescence.
The invention provides a preparation method of red light doped graphene quantum dots, which comprises the following steps: mixing a precursor material with a solvent to obtain a precursor solution; carrying out hydro-thermal synthesis treatment on the precursor solution to obtain a reaction product; and purifying the reaction product to obtain the red light doped graphene quantum dot.
In one embodiment, the precursor material comprises benzyl bromide and glucose.
In one embodiment, the concentration of benzyl bromide is 0.002 to 1mmol/L and the concentration of glucose is 0.02 to 5 mmol/mL.
In one embodiment, the solvent comprises one or more of ethanol, water, acetic acid, acetone, N-dimethylformamide.
In one embodiment, the precursor solution is treated by hydrothermal synthesis to obtain a reaction product comprising: and (3) placing the precursor solution in a high-temperature reaction kettle, and carrying out hydrothermal reaction at the temperature of 150-200 ℃ for 40-72h to obtain a reaction product containing the red light doped graphene quantum dots.
In an implementation manner, the purifying treatment of the reaction product to obtain the red-light-doped graphene quantum dot includes: filtering and dialyzing the reaction product to obtain filtrate; and drying the filtrate to obtain the red light doped graphene quantum dots.
In one embodiment, the reaction product is subjected to a filtration and dialysis process comprising: filtering with a filter membrane, wherein the filter membrane is an organic microporous filter membrane, and the pore diameter of the filter pores in the organic microporous filter membrane is 0.22-0.45 μm.
Subjecting the reaction product to filtration and dialysis treatment comprising: and (3) carrying out dialysis treatment by a dialysis bag, wherein the dialysis bag is an 800-14000Da dialysis bag, and the dialysis time is 2-5 days.
The invention further provides a red-light-doped graphene quantum dot, which is prepared by any one of the preparation methods of the red-light-doped graphene quantum dot.
In one embodiment, the emission peak of the fluorescence spectrum of the red-light-doped graphene quantum dot is located at 580-620 nm.
The red-light-doped graphene quantum dot provided by the invention has the advantages of good stability, higher quantum yield and higher fluorescence intensity. The preparation method of the red-light-doped graphene quantum dot provided by the embodiment of the invention is simple to operate, realizes the preparation of the graphene quantum dot with red fluorescence luminescence, and has high fluorescence intensity and high yield of the prepared graphene quantum dot. The red light doped graphene quantum dot and the preparation method thereof can be widely applied to the field of biological imaging.
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The above and other objects, features and advantages of exemplary embodiments of the present invention will become readily apparent from the following detailed description read in conjunction with the accompanying drawings. Several embodiments of the invention are illustrated by way of example, and not by way of limitation, in the figures of the accompanying drawings and in which:
in the drawings, the same or corresponding reference numerals indicate the same or corresponding parts.
Fig. 1 is a schematic flow chart of an implementation of a preparation method of red-light-doped graphene quantum dots according to an embodiment of the present invention;
fig. 2 is a captured fluorescence emission spectrum of the graphene quantum dot prepared in example 1 of the present invention;
fig. 3 is a fluorescence emission diagram of an aqueous solution of the graphene quantum dot prepared in example 1 of the present invention.
Detailed Description
In order to make the objects, features and advantages of the present invention more obvious and understandable, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present invention, and it is apparent that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Fig. 1 is a schematic flow chart of an implementation process of a preparation method of a red light doped graphene quantum dot according to an embodiment of the present invention.
Referring to fig. 1, an embodiment of the present invention provides a preparation method of a red light-doped graphene quantum dot, where the method includes: step 101, mixing a precursor material with a solvent to obtain a precursor solution; step 102, carrying out hydrothermal synthesis treatment on the precursor solution to obtain a reaction product; and 103, purifying the reaction product to obtain the red light doped graphene quantum dots.
The preparation method provided by the embodiment of the invention is used for preparing the red light doped graphene quantum dots, the red light doped graphene quantum dots prepared by the method have high fluorescence intensity and high yield, and emit red fluorescence under the irradiation of an ultraviolet lamp (365 nm). The method realizes the preparation of the red fluorescence luminescent graphene quantum dot, compared with the traditional method, the method is simpler to operate, and the prepared graphene quantum dot has the advantages of good thermal stability, light stability, high quantum yield and the like, and can be used as potential application in the field of biological imaging. Meanwhile, the red light doped graphene quantum dot has the characteristics of strong photobleaching resistance, low toxicity and controllability, and is expected to replace an inorganic quantum dot to be applied to the fields of biological analysis and medical imaging.
The method comprises the step of mixing a precursor material with a solvent to obtain a precursor solution. The precursor material is a raw material capable of obtaining red light doped graphene quantum dots, the precursor material can be one or more, and the precursor material can be mixed before being mixed with the solvent or can be mixed in the solvent. The solvent is a solvent capable of completely dissolving the precursor material, and can be an organic solvent, an inorganic solvent or a combination of the organic solvent and the inorganic solvent, and further, the solvent does not react with the precursor material. In order to achieve sufficient dissolution of the precursor material and the solvent, the embodiment of the present invention may adopt other methods that can sufficiently dissolve the precursor material and the solvent, such as increasing the proportion of the solvent in the solution, changing the temperature, mechanically stirring, and ultrasonically, wherein preferably, the precursor material and the solvent are mixed by magnetic stirring and ultrasonic to obtain the precursor solution.
The method also comprises the step of carrying out hydrothermal synthesis treatment on the precursor solution to obtain a reaction product. In the hydrothermal reaction of the precursor solution, the precursor material is synthesized to form a reaction product containing the red-light-doped graphene quantum dots. The hydrothermal synthesis treatment may be carried out by any synthesis method developed in the hydrothermal synthesis system, such as a direct method, a seed crystal method, a directing agent method, a template method, a complexing agent method, an organic solvent method, a microwave method, a high-temperature high-pressure synthesis technique, and the like, as required.
The method further comprises the step of purifying the reaction product to obtain the red light doped graphene quantum dots. After the reaction is finished, the reaction product at least comprises a solvent and an unreacted precursor material besides the red light doped graphene quantum dots, and the reaction product is a solution or a turbid solution. The reaction product needs to be purified to obtain the red light doped graphene quantum dots. The purification method can be filtration treatment, dialysis treatment, freeze drying, vacuum drying or other treatment methods, and according to the selection of the purification method, the red light doped graphene quantum dots prepared by the embodiment of the invention can be solution or solid powder.
In an embodiment of the present invention, the precursor material comprises benzyl bromide and glucose.
Benzyl bromide and glucose are used as precursor materials to carry out hydro-thermal synthesis, and a reaction product containing red light doped graphene quantum dots can be prepared. In another case, the precursor material may be generated by reaction in a solvent. Benzyl bromide and glucose contained in the precursor solution, i.e. the step of mixing the precursor material with the solvent is considered to have been performed.
In the embodiment of the invention, the concentration of the benzyl bromide is 0.002-1mmol/L, and the concentration of the glucose is 0.02-5 mmol/mL.
Wherein the concentration of benzyl bromide in the precursor solution can be selected from any one of 0.002-1mmol/L, such as 0.005mmol/L, 0.1mmol/L, 0.2mmol/L, 0.3mmol/L, 0.4mmol/L, 0.5mmol/L, 0.6mmol/L, 0.7mmol/L, 0.8mmol/L, 0.9 mmol/L. The concentration of glucose in the precursor solution can be selected from any value of 0.02-5mmol/mL, such as 0.05mmol/L, 1mmol/L, 2mmol/L, 3mmol/L, 4 mmol/L. Under the range, the method is favorable for the execution of the subsequent experiment steps on the premise of ensuring that the precursor material is fully dissolved.
In embodiments of the invention, the solvent comprises one or more of ethanol, water, acetic acid, acetone, N-dimethylformamide. In the solvent, benzyl bromide and glucose can be dissolved, and the solvent does not react with the benzyl bromide and the glucose in the process of forming a precursor solution and the process of hydrothermal synthesis reaction. It is further necessary to supplement that the amount of the substance of benzyl bromide is preferably 0.1 to 10mmol, the amount of the substance of glucose is preferably 1 to 50mmol, and the amount of the solvent is 10 to 50 mL.
In the embodiment of the present invention, the precursor solution is subjected to hydrothermal synthesis to obtain a reaction product, including: and (3) placing the precursor solution in a high-temperature reaction kettle, and carrying out hydrothermal reaction at the temperature of 150-200 ℃ for 40-72h to obtain a reaction product containing the red light doped graphene quantum dots.
The hydrothermal synthesis treatment of the embodiment of the invention is carried out in a high-temperature reaction kettle, and the lining material of the high-temperature reaction kettle is a material which does not react with the precursor solution and the reaction product, such as a lining made of polytetrafluoroethylene material and polyethylene material. The temperature of the hydrothermal reaction is controlled to be 150-200 ℃ in the hydrothermal reaction of the embodiment of the invention, and the time of the hydrothermal reaction is controlled to be 40-72 h. Preferably, the hydrothermal synthesis treatment in the embodiment of the invention specifically includes controlling the temperature of the hydrothermal reaction at 180 ℃ and controlling the time of the hydrothermal reaction at 48 hours, so that the reaction is sufficiently performed, and a reaction product containing the red-light-doped graphene quantum dots is obtained.
In the embodiment of the invention, the reaction product is purified to obtain the red light doped graphene quantum dot, and the method comprises the following steps: firstly, filtering and dialyzing a reaction product to obtain a filtrate; and then, drying the filtrate to obtain the red-light-doped graphene quantum dots.
Specifically, the purification treatment of the embodiment of the present invention includes subjecting the reaction product to filtration and dialysis treatment. The reaction product is filtered, filter residue and filtrate are separated, and the red light doped graphene quantum dots are stored in the filtrate. After filtering, performing further dialysis on the filtrate to reduce the content of impurities in the filtrate and improve the purity of the red light doped graphene quantum dots in the filtrate. After the red light doped graphene quantum dot solution is obtained, drying the filtrate to remove the solvent, thereby obtaining red light doped graphene quantum dot powder.
In the examples of the present invention, the reaction product was subjected to filtration and dialysis treatment comprising: filtering with a filter membrane, wherein the filter membrane is an organic microporous filter membrane, and the pore diameter of the filter pores in the organic microporous filter membrane is 0.22-0.45 μm.
Specifically, the filtering treatment in the embodiment of the present invention is performed by using a filter membrane, and according to the size of the components except for the red-light-doped graphene quantum dots, the filter membrane is preferably an organic microporous filter membrane, and the pore size of the pores in the organic microporous filter membrane is preferably 0.22 to 0.45 μm. Other membranes and pore sizes may be used to effect filtration of the reaction product.
In the present examples, the reaction product was subjected to filtration and dialysis treatments comprising: performing dialysis treatment through a dialysis bag, wherein the dialysis bag is 800-14000Da dialysis bag, and the dialysis time is 2-5 days.
Specifically, the dialysis treatment in the embodiment of the invention is performed by a dialysis bag, the dialysis bag is preferably a dialysis bag of 800-. Dialysis bags of other sizes and dialysis times can be used to perform dialysis of the filtrate as well.
To facilitate a further understanding of the above embodiments, two specific examples are provided below for illustration.
Example 1
First, 0.1mmol of benzyl bromide and 1mmol of glucose were obtained, and 10mL of ethanol was obtained as a solvent.
Then, 0.1mmol of benzyl bromide and 1mmol of glucose were mixed with 10mL of ethanol, and dissolved by sonication for 10min to form a precursor solution. And dissolving the benzyl bromide and the glucose in an ethanol solution to form a precursor solution. In the obtained precursor solution, the concentration of benzyl bromide is 0.01mmol/L, and the concentration of glucose is 0.1 mmol/mL.
And then transferring the precursor solution to a polytetrafluoroethylene reaction kettle with the capacity of 20mL, and heating at the high temperature of 180 ℃ for 48 hours to obtain a reaction product.
And then, filtering the reaction product through an organic microporous filter membrane with the aperture of 0.45 mu m, filtering to obtain filtrate, dialyzing the filtrate by adopting a 14000Da dialysis bag for 3 days to obtain dialysate, and freeze-drying the dialysate to obtain the graphene quantum dot powder.
Fig. 2 is a captured fluorescence emission spectrum of the graphene quantum dot prepared in example 1 of the present invention; fig. 3 is a fluorescence emission diagram of an aqueous solution of the graphene quantum dot prepared in example 1 of the present invention.
Referring to fig. 2 and 3, the graphene quantum dot powder obtained in example 1 was tested for fluorescence spectrum by a fluorescence spectrophotometer. The excitation wavelength of the fluorescence spectrophotometer was 503nm and the emission wavelength was 602 nm. As can be seen by capturing a fluorescence emission spectrum, the emission peak of the graphene quantum dot powder is located at 602 nm. As can be seen from the fluorescence luminescence diagram of the aqueous solution, the graphene quantum dot powder emits red fluorescence under the irradiation of an ultraviolet lamp (365 nm). The graphene quantum dot powder obtained in the embodiment 1 is placed in an environment of 80 ℃, and the excitation wavelength of a fluorescence spectrophotometer is 400-620 nm and the emission wavelength is 580-620nm through testing fluorescence spectrum. The graphene quantum dot powder obtained in the embodiment 1 is placed in daily illumination for 3 days, and the excitation wavelength of a fluorescence spectrophotometer is 400-620 nm and the emission wavelength is 580-620nm through testing fluorescence spectrum.
Example 2
First, 10mmol of benzyl bromide and 50mmol of glucose were obtained, and 30mL of ethanol was obtained as a solvent.
Then, 10mmol of benzyl bromide and 50mmol of glucose were mixed with 30mL of ethanol, and dissolved by sonication for 10min to form a precursor solution. And dissolving the benzyl bromide and the glucose in an ethanol solution to form a precursor solution. In the obtained precursor solution, the concentration of benzyl bromide is 0.03mmol/L, and the concentration of glucose is 1.1 mmol/mL.
And then transferring 10mL of the precursor solution into a polytetrafluoroethylene reaction kettle with the capacity of 20mL without transferring the precursor solution completely, and heating the precursor solution at the high temperature of 200 ℃ for 40 hours to obtain a reaction product.
And then, filtering the reaction product through an organic microporous filter membrane with the aperture of 0.22 mu m to obtain a filtrate, dialyzing the filtrate by adopting a 800Da dialysis bag for 5 days to obtain a dialysate, and freeze-drying the dialysate to obtain the graphene quantum dot powder.
The graphene quantum dot powder obtained in example 2 was tested for fluorescence spectrum by a fluorescence spectrophotometer. The excitation wavelength of the fluorescence spectrophotometer was 512nm, and the emission wavelength was 604 nm. The graphene quantum dot powder obtained in the embodiment 2 is placed in an environment of 80 ℃, and the excitation wavelength of a fluorescence spectrophotometer is 400-620 nm and the emission wavelength is 580-620nm through testing fluorescence spectrum. The graphene quantum dot powder obtained in the embodiment 2 is placed in daily illumination for 3 days, and the excitation wavelength of a fluorescence spectrophotometer is 400-620 nm and the emission wavelength is 580-620nm through testing fluorescence spectrum.
In another aspect, the embodiment of the invention provides a red-light-doped graphene quantum dot, which is prepared by any one of the preparation methods of the red-light-doped graphene quantum dots.
The red light doped graphene quantum dot provided by the embodiment of the invention is prepared by the preparation method provided by the embodiment, and the red light doped graphene quantum dot prepared by the method has the advantages of high fluorescence intensity, high yield, good thermal stability and light stability, and can emit red fluorescence under the irradiation of an ultraviolet lamp. The method realizes the preparation of the red fluorescence luminescent graphene quantum dot, compared with the traditional method, the method is simpler to operate, and the prepared graphene quantum dot has the advantages of good stability, higher quantum yield and the like, and can be used as potential application in the field of biological imaging. Specifically, the red light doped graphene quantum dot provided by the embodiment of the invention can still keep stable at 80 ℃, can still keep stable after being irradiated by ultraviolet light for 1-3 days, and has good thermal stability and light stability.
In the quantum yield of the red light doped graphene quantum dot provided by the embodiment of the invention, the ratio of the number of excited photons to the number of emitted photons is more than 40%, and is 5-20% higher than the quantum yield of other red light doped graphene quantum dots on the market.
In the embodiment of the invention, the fluorescence spectrum emission peak of the red light doped graphene quantum dot is located at 580-620 nm. Under the emission peak, the graphene quantum dots can be proved to contain red fluorescence.
In the description herein, references to the description of the term "one embodiment," "some embodiments," "an example," "a specific example," or "some examples," etc., mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples. Furthermore, various embodiments or examples and features of different embodiments or examples described in this specification can be combined and combined by one skilled in the art without contradiction.
Furthermore, the terms "first", "second" and "first" are used for descriptive purposes only and are not to be construed as indicating or implying relative importance or implicitly indicating the number of technical features indicated. Thus, a feature defined as "first" or "second" may explicitly or implicitly include at least one such feature. In the description of the present invention, "a plurality" means two or more unless specifically defined otherwise.
The above description is only for the specific embodiments of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention, and the changes or substitutions should be covered within the scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (7)
1. A preparation method of red light doped graphene quantum dots is characterized by comprising the following steps:
mixing a precursor material and a solvent to obtain a precursor solution, wherein the precursor material is benzyl bromide and glucose, and the solvent is ethanol;
placing the precursor solution in a high-temperature reaction kettle, and carrying out solvothermal synthesis treatment to obtain a reaction product;
purifying the reaction product to obtain red light doped graphene quantum dots;
carrying out solvothermal synthesis treatment on the precursor solution to obtain a reaction product, wherein the reaction product comprises: carrying out solvothermal reaction at the temperature of 150-200 ℃ for 40-72h to obtain a reaction product containing the red light doped graphene quantum dots.
2. The method of claim 1, wherein the concentration of benzyl bromide is 0.002 to 1mmol/L and the concentration of glucose is 0.02 to 5 mmol/mL.
3. The method according to claim 1, wherein the step of purifying the reaction product to obtain red-light-doped graphene quantum dots comprises:
filtering and dialyzing the reaction product to obtain filtrate;
and drying the filtrate to obtain the red light doped graphene quantum dots.
4. The method of claim 3, wherein the reaction product is subjected to filtration and dialysis comprising:
filtering with a filter membrane, wherein the filter membrane is an organic microporous filter membrane, and the pore diameter of the filter pores in the organic microporous filter membrane is 0.22-0.45 μm.
5. The method of claim 3, wherein the reaction product is subjected to filtration and dialysis comprising:
performing dialysis treatment through a dialysis bag, wherein the dialysis bag is an 800-14000Da dialysis bag, and the dialysis time is 2-5 days.
6. The red-light-doped graphene quantum dot is characterized by being prepared by the preparation method of any one of the red-light-doped graphene quantum dots of claims 1-5.
7. The red-light-doped graphene quantum dot according to claim 6, wherein the fluorescence spectrum emission peak of the red-light-doped graphene quantum dot is located at 580-620 nm.
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