CN110817843A - Eutectic solvent, application thereof, carbon quantum dot and preparation method thereof - Google Patents
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Abstract
The invention relates to the technical field of carbon material preparation, and particularly discloses a eutectic solvent, application thereof, a carbon quantum dot and a preparation method thereof. The eutectic solvent is prepared from a nitroimidazole compound and an alcohol compound in a molar ratio of 1: 7-9. The preparation method of the carbon quantum dots comprises the following steps: the eutectic solvent is reacted with cellulose nano crystal to prepare the cellulose nano crystal. The diameter distribution of the prepared carbon quantum dots is 1-5nm, the fluorescence quantum yield is 20-25%, and the prepared carbon quantum dots have good photoluminescence and high light resistance, and the preparation method provided by the invention not only reduces pollution generated in the preparation process and improves the material utilization rate, but also has the advantages of simple process, convenience in operation, low cost, low toxicity and environmental friendliness, is a low-cost, eco-friendly and resource-saving preparation method, and has wide application prospect.
Description
Technical Field
The invention relates to the technical field of carbon material preparation, in particular to a eutectic solvent, application thereof, a carbon quantum dot and a preparation method thereof.
Background
The carbon quantum dots are semiconductor nanocrystals with the radius smaller than or close to the Bohr radius of the laser, are nano-sized particles with unique optical and electrical characteristics, and are novel carbon-based zero-dimensional materials. As a nano fluorescent material, compared with the traditional organic dye molecules, the nano fluorescent material has the advantages of excellent optical property, good conductivity, water solubility, low toxicity, environmental friendliness, wide raw material source, low cost, good biocompatibility and the like, and has application values in the fields of luminescent devices, biological markers, biological detection, biosensors and the like.
At present, the synthesis method of the carbon quantum dots mainly comprises a hydrothermal method, a microwave radiation method, an arc discharge method, a laser etching method, a chemical oxidation method, ultrasonic treatment, an electrochemical method and the like. Among them, hydrothermal method and microwave method are the most widely used methods, and especially, the hydrothermal method is the most widely studied method for preparing carbon quantum dots with various organic small molecules (citric acid, glucose, amino acid, etc.) as carbon sources. The yield of the fluorescent carbon quantum dots prepared by the hydrothermal method is high, but the reaction conditions of high temperature and high pressure are required, the time consumption is long, and the cost is high. The microwave radiation method is simple and the preparation amount is large, but the separation of the synthesized carbon quantum dots and the raw materials is difficult, and a special reaction device is needed. The carbon quantum dots prepared by the method have the problems of unstable fluorescence capability, easy quenching under air or light conditions and low quantum yield. Therefore, the development of a synthesis method of the carbon quantum dots which are more green, simple and convenient and have low production cost and stable fluorescence capability has very important significance for expanding the application of the carbon quantum dots.
Disclosure of Invention
Aiming at the problems of complex operation, low quantum yield and unstable fluorescence capability of the carbon quantum dots in the process for preparing the carbon quantum dots in the prior art, the invention provides a eutectic solvent, application thereof, the carbon quantum dots and a preparation method thereof.
In order to solve the technical problems, the technical scheme provided by the invention is as follows:
a eutectic solvent is prepared from nitroimidazole compounds and alcohol compounds in a molar ratio of 1: 7-9.
Preferably, the nitroimidazole compound is at least one compound shown in formula I, wherein R is hydrogen or methyl, and X is hydrogen, chlorine or bromine.
Preferably, the alcohol compound is represented by the following general formula CnH2n+2OxWherein n is more than or equal to 1 and less than or equal to 10, and x is more than or equal to 1 and less than or equal to n.
Preferably, the preparation method of the eutectic solvent comprises the following steps: and (3) uniformly mixing the nitroimidazole compound and the alcohol compound, heating to 90-120 ℃, and keeping the temperature until the system is uniform and transparent to obtain the eutectic solvent.
Further preferably, the isothermal reaction time in the preparation method of the eutectic solvent is 1-3 h.
The invention also provides application of the eutectic solvent in preparation of carbon quantum dots.
The nitroimidazole compound contained in the preferred eutectic solvent can provide energy required in the synthesis process of preparing the carbon quantum dots, so that the reaction temperature can be reduced, the reaction time can be shortened, and the synthesis yield of the quantum dots can be improved.
The invention also provides a carbon quantum dot prepared by reacting any eutectic solvent with the cellulose nanocrystal.
Preferably, the mass ratio of the eutectic solvent to the cellulose nanocrystals is 2.5-3.0: 1.
Preferably, the preparation method of the cellulose nanocrystal comprises the following steps: adding cellulose into an acidifying agent to dissolve until the cellulose is saturated, heating to 80-100 ℃, preserving heat for 1-6h, performing ultrasonic treatment, cooling to room temperature, centrifuging, and drying to obtain the cellulose nanocrystal.
Further preferably, the time of the ultrasonic treatment is 8-12 min.
Preferably, the acidifying agent is prepared by reacting L-proline and oxalic acid at 30-60 deg.C at a molar ratio of 0.8-0.83: 1.
Further preferably, the reaction time for the preparation of the acidifying agent is 1.5 to 2 hours.
According to the invention, the eutectic solvent of L-proline and oxalic acid is preferably selected as the cellulose acidifier, so that the innocuity of the acidifier can be ensured, the cellulose is acidified according to the preparation method, the crystallinity of the cellulose nanocrystal can be improved, the crystallinity of the prepared nanocellulose can reach 70-80%, and meanwhile, the uniformity of the particle size of the prepared cellulose nanocrystal is facilitated, the dispersibility of the prepared carbon quantum dots is further facilitated, the diameters of the carbon quantum dots are smaller and uniform, the content of carbon with a graphene structure in the carbon quantum dots can be improved, and the fluorescence performance of the carbon quantum dots is improved.
Preferably, the cellulose is absorbent cotton, eucalyptus powder or microcrystalline cellulose.
The invention also provides a preparation method of the carbon quantum dots, which comprises the following steps:
and mixing the eutectic solvent and the cellulose nanocrystals, heating to 240 ℃ at 200 ℃, and carrying out hydrothermal reaction for 10-16h to obtain the carbon quantum dots.
Preferably, the eutectic solvent is suction filtered before mixing it with the cellulose nanocrystals.
Further preferably, the suction filtration is carried out by sand core suction filtration using a filter paper having a pore size of 0.22 μm.
Compared with the prior art, the preparation method of the carbon quantum dot provided by the invention has the advantages that nitroimidazole compounds and alcohol compounds are used as raw materials to form the eutectic solvent with good chemical stability, the eutectic solvent system has good uniformity, and the solubility of the cellulose nanocrystal can be increased, so that the reactants are contacted more sufficiently, the dispersibility of the carbon quantum dot is improved, meanwhile, the eutectic solvent can be used for modifying the nitro group on the surface of the carbon quantum dot, the surface fluorescence active sites of the carbon quantum dot are enriched, and N in the nitro group can form a conjugated structure with adjacent carbon atoms, so that protons captured by the N atoms are transferred to the conjugated carbon structure, the fluorescence quantum yield is improved, the functionalized regulation and control of the fluorescence performance of the carbon quantum dot can be realized, and the application range of the carbon quantum dot is effectively widened.
The method synthesizes the carbon quantum dots on the basis of the nitroimidazole eutectic solvent coupled cellulose nanocrystals, the prepared carbon quantum dots have the diameter distribution of 1-5nm and the fluorescence quantum yield of 20-25%, and have good photoluminescence and high light resistance.
Drawings
FIG. 1 is a TEM image of a carbon quantum dot prepared by an example of the present invention;
FIG. 2 is a High Resolution Scanning Electron Microscope (HRSEM) image of carbon quantum dots prepared according to an embodiment of the present invention;
FIG. 3 is a fluorescence spectrum of carbon quantum dots prepared according to an embodiment of the present invention, wherein the fluorescence spectrum is 270nm, 290nm, 275nm, 285nm and 280nm from bottom to top;
FIG. 4 is a particle size distribution diagram of carbon quantum dots prepared according to an embodiment of the present invention;
FIG. 5 is a graph showing the maximum fluorescence intensity of carbon quantum dots prepared according to an example of the present invention as a function of the standing time.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
In order to better illustrate the invention, the following examples are given by way of further illustration.
Example 1
The embodiment of the invention provides a eutectic solvent, which is prepared from 5-chloro-1-methyl-4-nitroimidazole and glycerol in a molar ratio of 1:7, and specifically comprises the following steps:
mixing 0.01mol (1.62g) of 5-chloro-1-methyl-4-nitroimidazole and 0.07mol (6.45g) of glycerol, heating to 90 ℃, and reacting at constant temperature for 3 hours to make the system uniform and transparent to obtain the nitroimidazole eutectic solvent.
Example 2
The embodiment of the invention provides a eutectic solvent, which is prepared from 2-chloro-4-nitroimidazole and ethylene glycol in a molar ratio of 1:8, and specifically comprises the following steps:
mixing 0.01mol (1.48g) of 2-chloro-4-nitroimidazole and 0.08mol (4.97g) of ethylene glycol, heating to 105 ℃, reacting at constant temperature for 2 hours to make the system uniform and transparent, and obtaining the nitroimidazole eutectic solvent.
Example 3
The embodiment of the invention provides a eutectic solvent, which is prepared from 5-chloro-1-methyl-4-nitroimidazole and ethylene glycol in a molar ratio of 1:9, and specifically comprises the following steps:
mixing 0.01mol (1.62g) of 5-chloro-1-methyl-4-nitroimidazole and 0.09mol (5.58g) of ethylene glycol, heating to 115 ℃, and reacting at constant temperature for 1h to ensure that the system is uniform and transparent, thereby obtaining the nitroimidazole eutectic solvent.
Example 4
The embodiment of the invention provides a eutectic solvent, which is prepared from 5-chloro-1-methyl-4-nitroimidazole and ethylene glycol in a molar ratio of 1:9, and specifically comprises the following steps:
mixing 0.01mol (1.92g) of 2-bromo-4-nitroimidazole and 0.09mol (5.59g) of ethylene glycol, heating to 120 ℃, reacting at constant temperature for 1h to ensure that the system is uniform and transparent, and obtaining the eutectic solvent.
Example 5
The embodiment of the invention provides a eutectic solvent, which is prepared from 4-nitroimidazole and glycerol in a molar ratio of 1:8, and specifically comprises the following steps:
mixing 0.01mol (1.13g) of 4-nitroimidazole and 0.08mol (7.37g) of glycerol, heating to 110 ℃, reacting at constant temperature for 2 hours to make the system uniform and transparent, and obtaining the eutectic solvent.
Example 6
The embodiment of the invention provides a preparation method of carbon quantum dots, which comprises the following steps:
step one, uniformly mixing 0.08mol (9.21g) of L-proline and 0.1mol (12.61g) of oxalic acid, heating to 36 ℃, and reacting at constant temperature for 1.5h to ensure that the system is uniform and transparent to obtain the acidifier. Gradually adding a small amount of absorbent cotton into 14g of acidifier until the acidifier is saturated, heating to 95 ℃, performing oil bath for 1h, performing ultrasonic treatment for 10min, cooling to room temperature, centrifuging to obtain a solid, and freeze-drying to obtain a cellulose nanocrystal;
and step two, carrying out suction filtration treatment on the nitroimidazole eutectic solvent prepared in the embodiment 1 by using 0.22m filter paper, mixing the obtained mixture with the cellulose nanocrystal according to the mass ratio of 2.5:1, and carrying out hydrothermal reaction at 200 ℃ for 16h to obtain the carbon quantum dot.
Example 7
The embodiment of the invention provides a preparation method of carbon quantum dots, which comprises the following steps:
step one, uniformly mixing 0.083mol (9.56g) of L-proline and 0.1mol (12.61g) of oxalic acid, heating to 46 ℃, and reacting at constant temperature for 2 hours to make the system uniform and transparent to obtain the acidifier. Adding a small amount of eucalyptus powder into 14g of acidifying agent gradually until the acidifying agent is saturated, heating to 90 ℃, performing oil bath for 2h, performing ultrasonic treatment for 10min, cooling to room temperature, centrifuging to obtain a solid, and performing freeze drying to obtain a cellulose nanocrystal;
and step two, carrying out suction filtration treatment on the nitroimidazole eutectic solvent prepared in the embodiment 2 by using 0.22m filter paper, mixing the obtained mixture with the cellulose nanocrystal according to the mass ratio of 2.9:1, and carrying out hydrothermal reaction at 210 ℃ for 13 hours to obtain the carbon quantum dot.
Example 8
The embodiment of the invention provides a preparation method of carbon quantum dots, which comprises the following steps:
step one, uniformly mixing 0.08mol (9.21g) of L-proline and 0.1mol (12.61g) of oxalic acid, heating to 36 ℃, and reacting at constant temperature for 1.5h to ensure that the system is uniform and transparent to obtain the acidifier. Gradually adding a small amount of absorbent cotton into 14g of acidifier until the acidifier is saturated, heating to 100 ℃, performing oil bath for 1h, performing ultrasonic treatment for 10min, cooling to room temperature, centrifuging to obtain a solid, and freeze-drying to obtain a cellulose nanocrystal;
and step two, carrying out suction filtration treatment on the nitroimidazole eutectic solvent prepared in the embodiment 3 by using 0.22m filter paper, mixing the obtained mixture with the cellulose nanocrystal according to the mass ratio of 3.0:1, and carrying out hydrothermal reaction at 220 ℃ for 12 hours to obtain the carbon quantum dot.
In order to better illustrate the characteristics of the carbon quantum dots provided by the embodiments of the present invention, the carbon quantum dots prepared in example 8 were subjected to a correlation test, and the results are shown in the figure, wherein fig. 1 is a TEM image of the prepared carbon quantum dots, fig. 2 is a fluorescence spectrum diagram at different excitation wavelengths, and fig. 3 is a trend graph of the change of fluorescence intensity with the change of the standing time.
The TEM image of the carbon quantum dots prepared in the present embodiment is shown in FIG. 1, and it can be seen from the image that the carbon quantum dots are sphere-like, have small particle size and are distributed in the range of 3-10 nm. The High Resolution Scanning Electron Microscope (HRSEM) image of the carbon quantum dots prepared in this example is shown in fig. 2, and it can be seen from the image that the lattice fringe spacing is 0.16nm, confirming the presence of carbon of graphene structure. The fluorescence spectrum of the carbon quantum dots is shown in FIG. 3, and it can be seen from the graph that the fluorescence intensity of the carbon quantum dots is about 6000a.u. at the highest within the excitation wavelength range of 270-290 nm. The particle size distribution of the carbon quantum dots is shown in fig. 4, and it can be seen from the figure that the main particle size of the carbon quantum dots is 3 to 3.4 nm. As shown in fig. 5, the fluorescence intensity of the carbon quantum dots did not change much with the change in the standing time, and the standing 22d decreased only by 8.3%. The fluorescence quantum yield of the carbon quantum dots in this example was 21.4%.
Example 9
The embodiment of the invention provides a preparation method of carbon quantum dots, which comprises the following steps:
step one, uniformly mixing 0.083mol (9.56g) of L-proline and 0.1mol (12.61g) of oxalic acid, heating to 30 ℃, and reacting at constant temperature for 2 hours to make the system uniform and transparent to obtain the acidifier. Gradually adding a small amount of microcrystalline cellulose into 14g of acidifier until the acidifier is saturated, heating to 80 ℃, performing oil bath for 2.5h, performing ultrasonic treatment for 10min, cooling to room temperature, centrifuging to obtain a solid, and freeze-drying to obtain a cellulose nanocrystal;
and step two, carrying out suction filtration treatment on the nitroimidazole eutectic solvent prepared in the embodiment 4 by using 0.22m filter paper, mixing the obtained mixture with the cellulose nanocrystal according to the mass ratio of 2.9:1, and carrying out hydrothermal reaction at 240 ℃ for 10 hours to obtain the carbon quantum dot.
Example 10
The embodiment of the invention provides a preparation method of carbon quantum dots, which comprises the following steps:
step one, uniformly mixing 0.08mol (9.21g) of L-proline and 0.1mol (12.61g) of oxalic acid, heating to 60 ℃, and reacting at constant temperature for 1.5h to ensure that the system is uniform and transparent to obtain the acidifier. Adding a small amount of eucalyptus powder into 14g of acidifying agent gradually until the acidifying agent is saturated, heating to 80 ℃, performing oil bath for 2.5h, performing ultrasonic treatment for 10min, cooling to room temperature, centrifuging to obtain a solid, and freeze-drying to obtain a cellulose nanocrystal;
and step two, carrying out suction filtration treatment on the nitroimidazole eutectic solvent prepared in the embodiment 5 by using 0.22m filter paper, mixing the obtained mixture with the cellulose nanocrystal according to the mass ratio of 2.9:1, and carrying out hydrothermal reaction at 220 ℃ for 12 hours to obtain the carbon quantum dot.
The carbon quantum dots in the above other embodiments of the present invention have substantially equivalent effects to those in embodiment 8. And the carbon quantum dots prepared by the eutectic solvent prepared from the other nitroimidazole compounds and the alcohol compounds defined by the invention according to the preparation method can achieve the effect basically equivalent to that of the embodiment 8.
Comparative example 1
The comparative example provides a preparation method of a carbon quantum dot, which specifically comprises the following steps:
(1) uniformly mixing 0.01mol (2.20g) of 4-amino-5-bromoimidazole and 0.09mol (5.58g) of ethylene glycol, heating to 115 ℃, and reacting at constant temperature for 1h to ensure that the system is uniform and transparent to obtain an amino imidazole eutectic solvent;
(2) 0.08mol (9.21g) of L-proline and 0.1mol (12.61g) of oxalic acid were subjected to a compounding treatment. Heating to 56 ℃, reacting for 2 hours at constant temperature, and enabling the system to be uniform and transparent to obtain the acidifier. Gradually adding a small amount of absorbent cotton into 14g of acidifier until the acidifier is saturated, heating to 85 ℃, performing oil bath for 2.5h, performing ultrasonic treatment for 10min, cooling to room temperature, centrifuging to obtain a solid, and freeze-drying to obtain a cellulose nanocrystal;
(3) carrying out suction filtration treatment on the nitroimidazole eutectic solvent by using filter paper with the aperture of 0.22 mu m, adding cellulose nanocrystals according to the mass ratio of 2.9:1, and carrying out hydrothermal treatment at 220 ℃ for 12h to obtain the carbon quantum dots.
The carbon quantum prepared in the comparative example 1 is subjected to relevant tests, and the fluorescence intensity of the carbon quantum dot is about 4500a.u. at the highest within the excitation wavelength range of 270-290 nm. After being placed for 22 days, the fluorescence intensity of the carbon quantum dots is reduced by 17.7%. The fluorescence quantum yield of the carbon quantum dots in this comparative example was 18.8%.
Application example
A heavy metal detection experiment was performed on the carbon quantum dots prepared in example 8. A series of concentrations of 0.0001, 0.0003, 0.0005, 0.001, 0.003, 0.005, 0.01, 0.03, 0.05, 0.1, 0.3, 0.5, 1, 3, 5, 10, 30, 50 μmol · L are prepared-1Cu of (2)2+Solution, 1mLCu was added to 4mL of carbon quantum dot solution at room temperature2+After the solution, the change in fluorescence intensity was recorded. With Cu2+The increase in concentration decreases the fluorescence intensity of the carbon quantum dots. This shows that the prepared carbon quantum dots can be used for detecting Cu2+。
The carbon quantum dot in the embodiment of the invention takes the nitroimidazole compound and the alcohol compound as main raw materials to form the nitroimidazole eutectic solvent with good chemical stability, and takes the acidifying agent and the cellulose as raw materials to form the cellulose nanocrystal. Finally, the nitroimidazole eutectic solvent and the cellulose nanocrystal are mixed to prepare the carbon quantum dot through a hydrothermal method, the raw materials are low in toxicity and environment-friendly, the preparation is simple, the cost is low, the surface of the obtained carbon quantum dot is provided with nitro groups, the fluorescence quantum yield is high, the fluorescence stability is good, and the carbon quantum dot has a good application prospect in the field of heavy metal detection.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents or improvements made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (10)
1. The eutectic solvent is characterized by being prepared from a nitroimidazole compound and an alcohol compound in a molar ratio of 1: 7-9.
2. The eutectic solvent as claimed in claim 1, wherein the nitroimidazole compound is at least one compound shown as formula I, wherein R is hydrogen or methyl, and X is hydrogen, chlorine or bromine.
3. The eutectic solvent according to claim 1, wherein the alcohol compound is represented by the following formula CnH2n+2OxWherein n is more than or equal to 1 and less than or equal to 10, and x is more than or equal to 1 and less than or equal to n.
4. The eutectic solvent according to claim 1, wherein the eutectic solvent is prepared by a method comprising: and (3) uniformly mixing the nitroimidazole compound and the alcohol compound, heating to 90-120 ℃, and keeping the temperature until the system is uniform and transparent to obtain the eutectic solvent.
5. Use of the eutectic solvent according to any one of claims 1 to 4 for the preparation of carbon quantum dots.
6. A carbon quantum dot produced by reacting the eutectic solvent according to any one of claims 1 to 4 with a cellulose nanocrystal.
7. The carbon quantum dot of claim 6, wherein a mass ratio of the eutectic solvent to the cellulose nanocrystals is 2.5-3.0: 1.
8. The carbon quantum dot of claim 6, wherein the cellulose nanocrystal is prepared by: adding cellulose into an acidifying agent to dissolve until the cellulose is saturated, heating to 80-100 ℃, preserving heat for 1-2.5h, performing ultrasonic treatment, cooling to room temperature, centrifuging, and drying to obtain the cellulose nanocrystal.
9. The carbon quantum dot of claim 6, wherein the acidifying agent is prepared by reacting L-proline and oxalic acid in a molar ratio of 0.8-0.83:1 at 30-60 ℃.
10. A method for producing the carbon quantum dot according to any one of claims 6 to 9, characterized by comprising the steps of:
and mixing the eutectic solvent and the cellulose nanocrystals, heating to 240 ℃ at 200 ℃, and carrying out hydrothermal reaction for 10-16h to obtain the carbon quantum dots.
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| CN112011333A (en) * | 2020-08-12 | 2020-12-01 | 河北科技大学 | Nitrogen-containing carbon quantum dot and preparation method thereof |
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Cited By (3)
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| CN111892038A (en) * | 2020-08-12 | 2020-11-06 | 河北科技大学 | Acidic carbon quantum dot and preparation method and application thereof |
| CN112011333A (en) * | 2020-08-12 | 2020-12-01 | 河北科技大学 | Nitrogen-containing carbon quantum dot and preparation method thereof |
| CN111892038B (en) * | 2020-08-12 | 2023-03-10 | 河北科技大学 | Acidic carbon quantum dot and preparation method and application thereof |
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