CN110550616A - Energy-containing eutectic solvent, application thereof, metal-doped carbon quantum dot prepared from energy-containing eutectic solvent and preparation method of metal-doped carbon quantum dot - Google Patents
Energy-containing eutectic solvent, application thereof, metal-doped carbon quantum dot prepared from energy-containing eutectic solvent and preparation method of metal-doped carbon quantum dot Download PDFInfo
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Abstract
The invention relates to the technical field of carbon quantum dots, and particularly discloses an energy-containing eutectic solvent, application thereof, a metal-doped carbon quantum dot prepared from the energy-containing eutectic solvent and a preparation method of the metal-doped carbon quantum dot. The energetic eutectic solvent is prepared from an alcohol compound, a nitroimidazole energetic compound and a transition metal soluble salt. The energy-containing eutectic solvent is used for preparing the metal-doped carbon quantum dots. The metal-doped carbon quantum dot provided by the invention has the advantages of good dispersibility, good photoinduced charge transfer property, high chemical stability and high light resistance, and the preparation method has the advantages of simple process, convenience in operation, high raw material utilization rate, high energy utilization rate, low cost, low toxicity and environmental protection.
Description
Technical Field
The invention relates to the technical field of carbon quantum dots, in particular to an energy-containing eutectic solvent, application thereof, a metal-doped carbon quantum dot prepared from the energy-containing eutectic solvent and a preparation method of the metal-doped carbon quantum dot.
Background
Carbon quantum dots as a novel carbon-based zero-dimensional material are emerging in recent years, have excellent optical properties, good water solubility, low toxicity, environmental friendliness, biocompatibility and other advantages, and are widely applied to aspects of heavy metal identification, fluorescent probes, protein detection, drug transportation, biological imaging and the like. Metal nanomaterials are widely used as functional nanomaterials due to their advantages of high conductivity, good redox activity, etc. Therefore, the metal is combined with the carbon quantum dots by doping, so that the visible light response capability and the electron transmission efficiency of the carbon quantum dots can be enhanced, and the application of the carbon quantum dots in photocatalytic oxidation reaction is further expanded.
at present, the preparation method of the metal-doped carbon quantum dot mainly comprises a one-pot method and a step method. In the process of synthesizing the metal-doped carbon quantum dots by the one-pot method, the problems of low utilization rate of raw materials, waste of raw materials, poor dispersibility of the quantum dots, easy pollution to the environment and the like exist; the step method generally comprises the steps of preparing a metal nano material and a carbon quantum dot respectively, and then compounding and doping the metal nano material and the carbon quantum dot, wherein the carbon quantum dot and the metal material in the prepared metal-doped carbon quantum dot are not uniformly distributed, the interaction force is weak, and the chemical stability is poor.
Disclosure of Invention
Aiming at the problems of the existing metal-doped carbon quantum dots, the invention provides an energy-containing eutectic solvent, application thereof, a metal-doped carbon quantum dot prepared from the energy-containing eutectic solvent and a preparation method of the metal-doped carbon quantum dot.
In order to achieve the purpose of the invention, the embodiment of the invention adopts the following technical scheme:
An energy-containing eutectic solvent is prepared from alcohol compounds, nitroimidazole energy-containing compounds and soluble salt of transition metal.
compared with the prior art, the energy-containing eutectic solvent provided by the invention has the advantages that the alcohol compound is used as a hydrogen bond donor, the nitroimidazole energy-containing compound is used as a hydrogen bond acceptor, the transition metal soluble salt provides ligand metal ions, and the ligand metal ions are combined with each other through chemical bonds, so that the formed energy-containing eutectic solvent system has good uniformity and good chemical stability. The energy-containing eutectic solvent can be used for efficiently and environmentally preparing the metal-doped carbon quantum dots with excellent dispersibility.
Further, the molar ratio of the alcohol compound, the nitroimidazole energetic compound and the transition metal soluble salt is 2-3: 1-2: 0.1-0.5. The combination mode and the chemical stability of chemical bonds among reactants are influenced by the dosage proportion of the reactants, the molar ratio of the reactants is controlled, and the uniformity and the chemical stability of the energy-containing eutectic solvent system are ensured.
Further, the alcohol compound is at least one of the following general formulas C n H 2n+2 O x, wherein n is more than or equal to 1 and less than or equal to 5, and x is more than or equal to 1 and less than or equal to n.
furthermore, the nitroimidazole energetic compound is at least one of 1, 4-dinitroimidazole, 5-chloro-1-methyl-4-nitroimidazole, 2-methyl-4 (5) -nitroimidazole, 2,4, 5-trinitroimidazole or 1-methyl-2, 4, 5-trinitroimidazole. The nitroimidazole energetic compound has a high N content and is easier to form hydrogen bonds with H in an alcohol compound.
Further, the transition metal soluble salt is a transition metal chloride or a hydrate of the chloride, and the transition metal is nickel, iron, cobalt, manganese or zinc. The electron-rich group Cl in the transition metal soluble salt and H in the alcohol compound form hydrogen bonds, ligand metal ions are provided, and the ligand metal ions, the alcohol compound and the nitroimidazole energetic compound form a ligand compound, so that the chemical stability of the energetic eutectic solvent is improved.
further, the preparation method of the energy-containing eutectic solvent comprises the following steps: and mixing the alcohol compound, the nitroimidazole energetic compound and the transition metal soluble salt, heating to 90-110 ℃, and keeping the temperature until the system is uniform and transparent to obtain the energetic eutectic solvent.
Further, the heat preservation time is 1-6h, so that the alcohol compound and the nitroimidazole energetic compound are ensured to fully react with the transition metal soluble salt, and the energetic eutectic solvent with good system uniformity and good chemical stability is obtained.
the invention also provides application of the energy-containing eutectic solvent in metal-doped carbon quantum dots.
The invention also provides the metal-doped carbon quantum dot prepared from the energy-containing eutectic solvent.
The invention also provides a preparation method of the metal-doped carbon quantum dot, which comprises the following steps:
and mixing the energy-containing eutectic solvent with deionized water, and reacting at 80-150 ℃ for 4-10h to obtain the metal-doped carbon quantum dot.
The synthesis process of the eutectic solvent is mild and mainly forms by hydrogen bond donor and hydrogen bond acceptor through hydrogen bond association, so the high-energy chemical bond in the nitroimidazole energetic compound does not break and release energy in the step, but generates the energetic eutectic solvent, and the high-energy chemical bond such as C-NO 2 and N-NO 2 breaks and releases a large amount of energy in the further hydrothermal reaction process to reduce the reaction enthalpy in the whole reaction process.
Compared with the common eutectic solvent without energy, the energy consumption of the carbon quantum dot synthesis process based on the energetic eutectic solvent is greatly reduced, and the hydrothermal reaction time is greatly reduced. The carbon point hydrothermal reaction temperature based on the common energy-free eutectic solvent is 200-220 ℃, and the hydrothermal reaction temperature based on the energy-containing eutectic solvent is 80-150 ℃; the hydrothermal reaction time of the carbon point based on the common eutectic solvent without energy is 10-14 h, and the hydrothermal reaction time based on the eutectic solvent with energy is only 4-10 h.
Furthermore, the mass ratio of the energy-containing eutectic solvent to the deionized water is 1:20-30, so that the hydrothermal reaction is ensured to be smoothly carried out, the synthesis of the carbon quantum dots and the generation of surface groups of the carbon quantum dots are completed, and the chemical properties of the carbon quantum dots are improved.
Compared with the prior art, the preparation method of the metal-doped carbon quantum dot provided by the invention has the advantages that the alcohol compound, the nitroimidazole energetic compound and the transition metal soluble salt are used as main raw materials, the energetic eutectic solvent with good homogeneity and good chemical stability is formed firstly, the solubility of the nitroimidazole energetic compound is increased, the reactants are contacted more sufficiently, then the metal-doped carbon quantum dot is synthesized by adopting a hydrothermal reaction on the basis of the energetic eutectic solvent, the energy of the introduced nitroimidazole compound is fully utilized in the synthesis process, the material utilization rate is improved, the energy utilization rate is improved while the quantum dot synthesis yield is improved, the distribution form of the metal on the surface of the carbon quantum dot is optimized, and the obtained carbon quantum dot has good dispersibility. The preparation method has the advantages of simple process, convenient operation, high utilization rate of raw materials, low cost, low toxicity and environmental protection, and the obtained carbon quantum dots have good photoinduced charge transfer property, high chemical stability and high light resistance.
Drawings
FIG. 1 is a TEM image of a metal-doped carbon quantum dot in an embodiment of the present invention;
FIG. 2 is an EDS mapping diagram of metal-doped carbon quantum dots in an embodiment of the invention;
FIG. 3 is a UV spectrum of a metal-doped carbon quantum dot according to an embodiment of the present invention;
FIG. 4 is an excited fluorescence spectrum of a metal-doped carbon quantum dot in an embodiment of the present invention;
FIG. 5 is an emission fluorescence spectrum of metal-doped carbon quantum dots in an embodiment of the present invention;
FIG. 6 is a graph showing the results of the experiment on the resistance to fluorescent pH of carbon quantum dots in the example of the present invention;
FIG. 7 is a graph showing the effect of the standing time on the fluorescence intensity of carbon quantum dots in the example of the present invention.
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.
Example 1
an energy-containing eutectic solvent is prepared from glycerol, 1, 4-dinitroimidazole and zinc chloride in a molar ratio of 2:1:0.1, and comprises the following specific steps:
Mixing 0.2mol (18.418g) of glycerol, 0.1mol (15.807g) of 1, 4-dinitroimidazole and 0.01mol (1.363g) of zinc chloride, heating to 90 ℃, and reacting at constant temperature for 6 hours to ensure that the system is uniform and transparent, thereby obtaining the energy-containing eutectic solvent.
The energy-containing eutectic solvent is used for preparing the metal-doped carbon quantum dots, and the specific steps are as follows:
and mixing 2g of the energy-containing eutectic solvent and 60ml of deionized water, adding the mixture into a 100ml of polytetrafluoroethylene reaction kettle, and putting the reaction kettle into an air-blast drying oven to react for 10 hours at 80 ℃ to obtain the metal-doped carbon quantum dots.
Example 2
An energy-containing eutectic solvent is prepared from ethylene glycol, 5-chloro-1-methyl-4-nitroimidazole and NiCl 2.6H 2 O in a molar ratio of 3:2:0.5, and comprises the following specific steps:
mixing 0.3mol (18.621g) of ethylene glycol, 0.2mol (32.310g) of 5-chloro-1-methyl-4-nitroimidazole and 0.05mol (11.885g) of NiCl 2.6H 2 O, heating to 100 ℃, and reacting at constant temperature for 5 hours to ensure that the system is uniform and transparent, thereby obtaining the energy-containing eutectic solvent.
The energy-containing eutectic solvent is used for preparing the metal-doped carbon quantum dots, and the specific steps are as follows:
And mixing 2g of the energy-containing eutectic solvent and 60ml of deionized water, adding the mixture into a 100ml of polytetrafluoroethylene reaction kettle, and putting the reaction kettle into an air-blast drying oven to react for 4 hours at 100 ℃ to obtain the metal-doped carbon quantum dots.
Example 3
An energy-containing eutectic solvent is prepared from glycerol, 2-methyl-4 (5) -nitroimidazole and CoCl 2 & 6H 2 O in a molar ratio of 1:0.6:0.1, and comprises the following specific steps:
0.25mol (23.023g) of glycerol, 0.15mol (19.065g) of 2-methyl-4 (5) -nitroimidazole and 0.025mol (5.948g) of CoCl 2.6H 2 O are mixed, heated to 110 ℃, and reacted for 1 hour at constant temperature, so that the system is uniform and transparent, and the energy-containing eutectic solvent is obtained.
The energy-containing eutectic solvent is used for preparing the metal-doped carbon quantum dots, and the specific steps are as follows:
And mixing 2g of the energy-containing eutectic solvent and 40ml of deionized water, adding the mixture into a 100ml of polytetrafluoroethylene reaction kettle, and putting the reaction kettle into an air-blast drying oven to react for 6 hours at 90 ℃ to obtain the metal-doped carbon quantum dots.
Example 4
An energy-containing eutectic solvent is prepared from glycerol, 1, 4-dinitroimidazole and CoCl 2 & 6H 2 O in a molar ratio of 2:1:0.2 by the following specific steps:
0.24mol (22.102g) of glycerol, 0.12mol (18.97g) of 1, 4-dinitroimidazole and 0.024mol (5.710) of CoCl 2.6H 2 O are mixed, heated to 95 ℃, and reacted for 6 hours at constant temperature to ensure that the system is uniform and transparent, thus obtaining the energy-containing eutectic solvent.
The energy-containing eutectic solvent is used for preparing the metal-doped carbon quantum dots, and the specific steps are as follows:
And mixing 2g of the energy-containing eutectic solvent and 60ml of deionized water, adding the mixture into a 100ml of polytetrafluoroethylene reaction kettle, and putting the reaction kettle into an air-blast drying oven to react for 5 hours at 120 ℃ to obtain the metal-doped carbon quantum dots.
Example 5
An energy-containing eutectic solvent is prepared from glycerol, 2-methyl-4 (5) -nitroimidazole and zinc chloride in a molar ratio of 2.5:1:0.1, and comprises the following specific steps:
0.25mol (23.023g) of glycerol, 0.1mol (12.710g) of 2-methyl-4 (5) -nitroimidazole and 0.01mol (1.363g) of zinc chloride are mixed, heated to 90 ℃, and reacted for 6 hours at constant temperature to ensure that the system is uniform and transparent, thus obtaining the energy-containing eutectic solvent.
The energy-containing eutectic solvent is used for preparing the metal-doped carbon quantum dots, and the specific steps are as follows:
And mixing 2g of the energy-containing eutectic solvent with 60ml of deionized water, adding the mixture into a 100ml of polytetrafluoroethylene reaction kettle, and putting the reaction kettle into an air-blast drying oven to react for 4 hours at 150 ℃ to obtain the metal-doped carbon quantum dots.
In order to better illustrate the characteristics of the metal-doped carbon quantum dots provided by the embodiments of the present invention, the metal-doped carbon quantum dots prepared in example 3 were tested for their corresponding properties.
Based on a TEM image of the metal-doped carbon quantum dots containing the energy eutectic solvent, as shown in figure 1, the metal-doped carbon quantum dots are sphere-like, have small particle size and are completely dispersed without any agglomeration phenomenon. As shown in fig. 2, which is an EDS mapping diagram of the metal-doped carbon quantum dot, it is shown that a large amount of cobalt element exists in the carbon quantum dot and is uniformly distributed, and it is further proved that the obtained metal-doped carbon quantum dot is a metal-doped carbon quantum dot and has good dispersibility.
The optical properties of the metal-doped carbon quantum dots provided by the embodiment of the invention are researched by using ultraviolet spectrum and fluorescence spectrum. The ultraviolet spectrogram of the metal-doped carbon quantum dot is shown in fig. 3, and a relatively obvious ultraviolet absorption peak appears at 290nm, which is caused by pi → pi transition of N ═ O in the carbon quantum dot. FIG. 4 shows an excitation fluorescence spectrum with a maximum excitation wavelength of 410nm, and FIG. 5 shows an emission fluorescence spectrum with a maximum emission wavelength of 470 nm. The data show that the metal-doped carbon quantum dot provided by the invention has good photoinduced charge transfer performance.
in addition, the ph tolerance experiment (as shown in fig. 6) and the influence experiment of the standing time (under normal visible light conditions) on the fluorescence intensity of the carbon quantum dots (as shown in fig. 7) were performed on the metal-doped carbon quantum dots obtained in example 3, and the results show that: the metal-doped carbon quantum dot has small fluctuation range of fluorescence intensity under different pH values, and the fluorescence intensity is basically kept stable along with the increase of time. The metal-doped carbon quantum dots in the other embodiments described above have the effect equivalent to that of embodiment 3.
The metal-doped carbon quantum dots have the advantages of good dispersibility, good photoinduced charge transfer property, high chemical stability and high light resistance, and the preparation method has the advantages of simple process, convenient operation, high utilization rate of raw materials, high energy utilization rate, low cost, low toxicity and environmental protection.
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. an energetic eutectic solvent, characterized in that: is prepared from alcohol compounds, nitroimidazole energetic compounds and soluble transition metal salts.
2. the energetic eutectic solvent of claim 1, characterized by: the molar ratio of the alcohol compound, the nitroimidazole energetic compound and the transition metal soluble salt is 2-3: 1-2: 0.1-0.5.
3. The energetic eutectic solvent according to claim 1, characterized in that the alcohol compound is at least one of the following general formulas C n H 2n+2 O x, wherein n is 1. ltoreq. n.ltoreq.5, and x is 1. ltoreq. x.ltoreq.n.
4. the energetic eutectic solvent of claim 1, characterized by: the nitroimidazole energetic compound is at least one of 1, 4-dinitroimidazole, 5-chloro-1-methyl-4-nitroimidazole, 2-methyl-4 (5) -nitroimidazole, 2,4, 5-trinitroimidazole or 1-methyl-2, 4, 5-trinitroimidazole.
5. The energetic eutectic solvent of claim 1, characterized by: the transition metal soluble salt is transition metal chloride or hydrate of the chloride, and the transition metal is nickel, iron, cobalt, manganese or zinc.
6. The energetic eutectic solvent according to any one of claims 1 to 5, characterized in that: the preparation method of the energy-containing eutectic solvent comprises the following steps: and mixing the alcohol compound, the nitroimidazole energetic compound and the transition metal soluble salt, heating to 90-110 ℃, and keeping the temperature until the system is uniform and transparent to obtain the energetic eutectic solvent.
7. Use of the energy-containing eutectic solvent of any one of claims 1 to 6 in the preparation of metal-doped carbon quantum dots.
8. A metal-doped carbon quantum dot is characterized in that: prepared from the energetic eutectic solvent of any one of claims 1 to 6.
9. A method for preparing the metal-doped carbon quantum dot according to claim 8, wherein the method comprises the following steps: the method comprises the following steps:
And mixing the energy-containing eutectic solvent with deionized water, and reacting at 80-150 ℃ for 4-10h to obtain the metal-doped carbon quantum dot.
10. The method of preparing metal-doped carbon quantum dots according to claim 9, wherein: the mass ratio of the energy-containing eutectic solvent to the deionized water is 1: 20-30.
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