CN111849474A - Nitrogen-doped carbon dots based on carnation flowers and preparation method and application thereof - Google Patents
Nitrogen-doped carbon dots based on carnation flowers and preparation method and application thereof Download PDFInfo
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Abstract
The invention provides a nitrogen-doped carbon dot based on carnation flowers and a preparation method and application thereof. The method takes withered carnation petals and polyethyleneimine as precursors and secondary water as a solvent, and after ultrasonic treatment, the solution mixture is heated in a high-pressure kettle for reaction. The autoclave was then allowed to cool to room temperature and filtered through filter paper to remove large particles. After that, the dark brown filtrate was further filtered through a cylindrical filter membrane filter. To obtain aBased on nitrogen-doped carbon dots of carnation flowers. The method for preparing the carbon quantum dots is simple, low in cost and easy in obtaining of raw materials. The prepared carbon quantum dot has stable optical property and low biological toxicity. The carbon quantum dot can be used for detecting vitamin B in commercial orange juice, soybean milk, honey, B vitamin tablets and multi-vitamin complex vitamin tablets2(VB2) Content of and use for intracellular VB2And pH sensing, and can be used for preparing fluorescent color development coating with pH control.
Description
Technology neighborhood
The invention relates to a luminescent nano material, in particular to nitrogen-doped carbon dots (N-CDs) based on carnation flowers, and a preparation method and application thereof.
Background
With the development of carbon nanomaterials, Carbon Dots (CDs), an emerging luminescent carbon nanomaterial, have received much attention due to their excellent optical and chemical properties. As fluorescent nanoparticles with the size less than 10nm, the carbon dots have unique properties such as easy preparation and functionalization, good water solubility, high light stability, excellent biocompatibility and biomarker potential compared with organic fluorescent dyes and conventional semiconductor quantum dots, and are widely applied to aspects such as fluorescence sensing, photoelectric equipment, biological imaging, biomedicine and the like.
At present, some carbon dots synthesized by using natural products as raw materials also show various applications. For example: some researchers have used synthetic carbon quantum dots such as milk, honey, silk, hair, lemon, etc. for bio-imaging, printing patterns and sensing. Some researchers have used egg white, yolk and eggshell as raw materials to synthesize carbon dots for DNA binding and recognition, respectively, Fe3+Detection and biological imaging. The carbon dots synthesized by using the fish scales and the crab shells as raw materials can be used for biosensing and diagnosis and treatment. Therefore, the method takes cheap and easily-obtained natural products as raw materials, synthesizes different multifunctional fluorescent carbon dots by using a simple strategy, and has important significance in realizing the application of the carbon dots in multiple aspects.
Disclosure of Invention
The invention aims to provide nitrogen-doped carbon dots based on carnation flowers and a preparation method and application thereof, wherein the preparation method is simple, the cost is low, and raw materials are easy to obtain; the prepared carbon quantum dots can be used for detecting orange juice and soybean milkVB in milk, honey, B vitamin tablets and multi-vitamin complex tablets2Content of and use for intracellular VB2And pH sensing, and can also be used to prepare pH controlled fluorescent color developing coatings.
The invention provides a preparation method of nitrogen-doped carbon dots based on carnation flowers, which comprises the following steps:
1) putting the dried carnation petals in a beaker, adding secondary water, adding polyethyleneimine into the solution, and performing ultrasonic treatment to obtain a mixed solution; the mass ratio of the dried carnation petals to the polyethyleneimine to the secondary water is 0.3-0.7: 0.3-0.7: 10-15 parts of;
2) and (3) placing the solution subjected to ultrasonic treatment in a high-pressure reaction kettle, carrying out hydrothermal reaction for 3-5h at the temperature of 120-170 ℃, naturally cooling the high-pressure reaction kettle to room temperature, and filtering with filter paper to remove large particles in the solution after reaction. Then, the dark brown filtrate was further filtered through a cylindrical filter membrane filter (0.22 μm) to obtain a nitrogen-doped carbon dot aqueous solution based on carnation flowers;
3) and (3) freeze-drying the carbon dot aqueous solution to obtain the nitrogen-doped carbon dots based on the carnation flowers.
The mass ratio of the dried carnation petals, the polyethyleneimine and the secondary water in the step 1) is preferably 0.5:0.5: 12.
The hydrothermal reaction temperature in the step 2) is preferably 150 ℃, and the reaction time is preferably 3 h.
The nitrogen-doped carbon dots prepared by the method can be used for VB in commercial orange juice, soybean milk, honey, B vitamin tablets and multi-vitamin complex tablets2Detecting the content of VB in cells2And pH sensing.
The fluorescent paint with the color development controlled by the pH value provided by the invention contains the nitrogen-doped carbon dots based on the carnation flowers.
A preparation method of a fluorescent paint with color development controlled by pH comprises the following steps: adding polyvinyl alcohol into secondary water, heating to fully dissolve the polyvinyl alcohol, adding an ethanol solution in which fluorane dye and epoxy resin are dissolved, fully stirring and mixing the mixture, slightly cooling the mixture for 10 minutes, adding the nitrogen-doped carbon dot solution based on carnation flowers into the mixture, fully stirring the mixture, and uniformly mixing the mixture to obtain the pH-controlled color-developable fluorescent paint.
The mass ratio of the polyvinyl alcohol, the secondary water, the ethanol, the fluorane dye, the epoxy resin and the nitrogen-doped carbon dots is 2-4:20:5-8:0.05-0.1:0.02-0.05: 0.004-0.01.
The fluorescent paint with the color development controlled by the pH value prepared by the method can be used for developing the color of the paint by acid, the fluorescence of a developing part is particularly strong, the fluorescence cannot be developed by alkali, and the fluorescence is very weak.
Compared with the prior art, the invention has the beneficial effects that:
the nitrogen-doped carbon dots based on carnation flowers are synthesized by a one-step hydrothermal method by using withered carnation petals as a carbon source and a polyethyleneimine water-soluble high-molecular polymer as a nitrogen source.
The dried carnation petals as natural products widely exist in the natural world, are green and environment-friendly, and are low in cost and easy to obtain; the polyethyleneimine serving as a common reagent has wide source and contains a large amount of-NH-functional groups, so that the surface of the carbon dot contains a large amount of nitrogen-containing functional groups.
The quantum yield of the nitrogen-doped carbon dots is high, and the relative quantum yield of the obtained nitrogen-doped carbon dots is generally between 8 and 13 percent by taking quinine sulfate (the quantum yield is 54 percent) as a reference.
The nitrogen-doped carbon dots prepared by the method can be used for VB in commercial orange juice, soybean milk, honey, vitamin B tablets and multi-vitamin complex tablets2Content detection and application to intracellular VB2Can also be used for intracellular pH sensing.
The fluorescent paint with the color development controlled by pH value prepared by the invention can be used as a writing board in a classroom, can emit blue light in the dark, and can be used for writing with an acid pen to develop pink characters.
In a word, the method has the advantages of simple operation process, easily obtained raw materials, environmental protection, low requirement on preparation conditions, stable optical property of the obtained nitrogen-doped carbon dots and fluorescence quantumHigh yield, and the carbon quantum dot as ratio type fluorescence sensor for detecting VB2And the method has wider linear range and better sensitivity. Can be used for VB in commercial orange juice, soybean milk, honey, vitamin B tablets and multi-vitamin complex tablets2Content detection, good photostability, low toxicity, and application for intracellular VB2And pH sensing, can also be used to prepare pH controlled color developable fluorescent coatings.
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FIG. 1 is a spectrum of fluorescence emission of nitrogen-doped carbon dots based on carnation flower prepared in example 1 showing excitation wavelength independence
FIG. 2 shows the UV absorption spectrum and fluorescence excitation and emission spectrum of a nitrogen-doped carbon dot based on carnation flower prepared in example 1
FIG. 3 is a full XPS spectrum of nitrogen doped carbon dots based on carnation flowers prepared in example 1
FIG. 4 shows nitrogen-doped carbon dot detection VB based on carnation flower prepared in example 12Fluorescence spectrum titration chart of
FIG. 5 is a graph showing the ratio of the fluorescence intensity at 470nm and 532nm of the nitrogen-doped carbon dots based on carnation flower prepared in example 1 (F)532/F470) Following VB2Working curve of concentration change
FIG. 6 is a graph showing the fluorescence titration spectrum and the working curve of the nitrogen-doped carbon dots of carnation flower at 470nm according to example 1
FIG. 7 shows the result of using the nitrogen-doped carbon dots based on carnation flower prepared in example 1 for the intracellular VB of Hela cell2The image of the cell confocal imaging is a cell fluorescence image of a dark field blue light channel under 405nm excitation, a cell fluorescence image of a green light channel and a combined image of the two channels.
FIG. 8 is a graph of confocal images of Hela cells at different pH values using nitrogen-doped carbon dots based on carnation flowers prepared in example 1, showing the fluorescence of cells in a dark-field blue channel and green channel under 405nm excitation, and the combination of the two channels.
Detailed Description
The present invention is described in detail with reference to the following examples, which show detailed embodiments and specific procedures, but the scope of the present invention is not limited to the following examples.
Example 1
1) Putting 0.5g of dried carnation petals in a beaker, adding 12mL of secondary water, adding 0.5g of polyethyleneimine into the solution, and performing ultrasonic treatment to obtain a mixed solution;
2) putting the solution subjected to ultrasonic treatment in a high-pressure reaction kettle, and carrying out hydrothermal reaction for 3h at 150 ℃;
3) after the reaction is stopped, naturally cooling the high-pressure reaction kettle to room temperature, and filtering by using filter paper to remove large particles in the solution after the reaction; then, the dark brown filtrate was further filtered through a cylindrical filter membrane filter (0.22 μm) to obtain a nitrogen-doped carbon dot aqueous solution based on carnation flowers;
4) and (3) freeze-drying the carbon quantum dot aqueous solution to obtain the target carbon quantum dot, wherein the relative quantum yield (based on quinine sulfate) of the target carbon quantum dot is 13%.
5) The characterization and application of properties are shown in FIGS. 1-8, Table 1.
preparing the fluorescent paint with pH control color development: adding 3g of polyvinyl alcohol into 20mL of secondary water, heating to fully dissolve, adding 5mL of ethanol solution in which 0.1g of fluorane dye and 0.03g of epoxy resin are dissolved, fully stirring and mixing, slightly cooling for 10 minutes, adding 2mL of carnation flower-based nitrogen-doped carbon dot solution (3mg/mL), fully stirring, and uniformly mixing to obtain the fluorescent paint with pH control color development.
Example 2
1) Putting 0.3g of dried carnation petals in a beaker, adding 10mL of secondary water, adding 0.5g of polyethyleneimine into the solution, and performing ultrasonic treatment to obtain a mixed solution;
2) putting the solution subjected to ultrasonic treatment in a high-pressure reaction kettle, and carrying out hydrothermal reaction for 3h at 150 ℃;
3) after the reaction is stopped, naturally cooling the high-pressure reaction kettle to room temperature, and filtering by using filter paper to remove large particles in the solution after the reaction; then, the dark brown filtrate was further filtered through a cylindrical filter membrane filter (0.22 μm) to obtain a nitrogen-doped carbon dot aqueous solution based on carnation flowers;
4) and (3) freeze-drying the carbon quantum dot aqueous solution to obtain the target carbon quantum dot, wherein the relative quantum yield (taking quinine sulfate as a standard) of the target carbon quantum dot is 8%.
preparing the fluorescent paint with pH control color development: adding 3g of polyvinyl alcohol into 20mL of secondary water, heating to fully dissolve, adding 5mL of ethanol solution in which 0.1g of fluorane dye and 0.03g of epoxy resin are dissolved, fully stirring and mixing, slightly cooling for 10 minutes, adding 2mL of carnation flower-based nitrogen-doped carbon dot solution (3mg/mL), fully stirring, and uniformly mixing to obtain the pH-controlled color-developable fluorescent paint.
Example 3
1) Putting 0.7g of dried carnation petals in a beaker, adding 15mL of secondary water, adding 0.5g of polyethyleneimine into the solution, and performing ultrasonic treatment to obtain a mixed solution;
2) putting the solution subjected to ultrasonic treatment in a high-pressure reaction kettle, and carrying out hydrothermal reaction for 3h at 150 ℃;
3) after the reaction is stopped, naturally cooling the high-pressure reaction kettle to room temperature, and filtering by using filter paper to remove large particles in the solution after the reaction; then, the dark brown filtrate was further filtered through a cylindrical filter membrane filter (0.22 μm) to obtain a nitrogen-doped carbon dot aqueous solution based on carnation flowers;
4) and (3) freeze-drying the carbon quantum dot aqueous solution to obtain the target carbon quantum dot, wherein the relative quantum yield (taking quinine sulfate as a standard) of the target carbon quantum dot is 10%.
preparing the fluorescent paint with pH control color development: adding 3g of polyvinyl alcohol into 20mL of secondary water, heating to fully dissolve, adding 5mL of ethanol solution in which 0.1g of fluorane dye and 0.03g of epoxy resin are dissolved, fully stirring and mixing, slightly cooling for 10 minutes, adding 2mL of carnation flower-based nitrogen-doped carbon dot solution (3mg/mL), fully stirring, and uniformly mixing to obtain the pH-controlled color-developable fluorescent paint.
Example 4
1) Putting 0.5g of dried carnation petals in a beaker, adding 15mL of secondary water, adding 0.7g of polyethyleneimine into the solution, and performing ultrasonic treatment to obtain a mixed solution;
2) putting the solution subjected to ultrasonic treatment in a high-pressure reaction kettle, and carrying out hydrothermal reaction for 3h at 150 ℃;
3) after the reaction is stopped, naturally cooling the high-pressure reaction kettle to room temperature, and filtering by using filter paper to remove large particles in the solution after the reaction; then, the dark brown filtrate was further filtered through a cylindrical filter membrane filter (0.22 μm) to obtain a nitrogen-doped carbon dot aqueous solution based on carnation flowers;
4) and (3) freeze-drying the carbon quantum dot aqueous solution to obtain the target carbon quantum dot, wherein the relative quantum yield (based on quinine sulfate) of the target carbon quantum dot is 11%.
preparing the fluorescent paint with pH control color development: 4) adding 3g of polyvinyl alcohol into 20mL of secondary water, heating to fully dissolve, adding 5mL of ethanol solution in which 0.1g of fluorane dye and 0.03g of epoxy resin are dissolved, fully stirring and mixing, slightly cooling for 10 minutes, adding 2mL of carnation flower-based nitrogen-doped carbon dot solution (3mg/mL), fully stirring, and uniformly mixing to obtain the pH-controlled color-developable fluorescent paint.
Example 5
1) Putting 0.5g of dried carnation petals in a beaker, adding 12mL of secondary water, adding 0.5g of polyethyleneimine into the solution, and performing ultrasonic treatment to obtain a mixed solution;
2) putting the solution subjected to ultrasonic treatment in a high-pressure reaction kettle, and carrying out hydrothermal reaction for 5 hours at the temperature of 120 ℃;
3) after the reaction is stopped, naturally cooling the high-pressure reaction kettle to room temperature, and filtering by using filter paper to remove large particles in the solution after the reaction; then, the dark brown filtrate was further filtered through a cylindrical filter membrane filter (0.22 μm) to obtain a nitrogen-doped carbon dot aqueous solution based on carnation flowers;
4) and (3) freeze-drying the carbon quantum dot aqueous solution to obtain the target carbon quantum dot, wherein the relative quantum yield (taking quinine sulfate as a standard) of the target carbon quantum dot is 9%.
preparing the fluorescent paint with pH control color development: adding 3g of polyvinyl alcohol into 20mL of secondary water, heating to fully dissolve, adding 5mL of ethanol solution in which 0.1g of fluorane dye and 0.03g of epoxy resin are dissolved, fully stirring and mixing, slightly cooling for 10 minutes, adding 2mL of carnation flower-based nitrogen-doped carbon dot solution (3mg/mL), fully stirring, and uniformly mixing to obtain the pH-controlled color-developable fluorescent paint.
Example 6
1) Putting 0.5g of dried carnation petals in a beaker, adding 12mL of secondary water, adding 0.5g of polyethyleneimine into the solution, and performing ultrasonic treatment to obtain a mixed solution;
2) putting the solution subjected to ultrasonic treatment in a high-pressure reaction kettle, and carrying out hydrothermal reaction for 2h at 170 ℃;
3) after the reaction is stopped, naturally cooling the high-pressure reaction kettle to room temperature, and filtering by using filter paper to remove large particles in the solution after the reaction; then, the dark brown filtrate was further filtered through a cylindrical filter membrane filter (0.22 μm) to obtain a nitrogen-doped carbon dot aqueous solution based on carnation flowers;
4) and (3) freeze-drying the carbon quantum dot aqueous solution to obtain the target carbon quantum dot, wherein the relative quantum yield (based on quinine sulfate) of the target carbon quantum dot is 12%.
preparing the fluorescent paint with pH control color development: adding 3g of polyvinyl alcohol into 20mL of secondary water, heating to fully dissolve, adding 5mL of ethanol solution in which 0.1g of fluorane dye and 0.03g of epoxy resin are dissolved, fully stirring and mixing, slightly cooling for 10 minutes, adding 2mL of carnation flower-based nitrogen-doped carbon dot solution (3mg/mL), fully stirring, and uniformly mixing to obtain the pH-controlled color-developable fluorescent paint.
Example 7
Nitrogen-doped carbon dot detectable VB prepared from carnation flower based example 12As shown in FIG. 4, VB was gradually added dropwise to the carbon dot solution2Solution with VB2The increase in concentration, the intensity of the fluorescence peak at 470nm, is gradualDecreasing while the fluorescence peak intensity at 532nm gradually increases.
Example 8
Nitrogen-doped carbon dot detection VB prepared in example 1 and based on carnation flowers2As shown in fig. 5: in the range of 0.35-35.9. mu.M, F532/F470And VB2The concentration has good linear relation, and the linear equation is F532/F470=0.3071+0.0376x(VB2Concentration), R20.99693; wherein, F470Is VB2Fluorescence intensity of carbon spot at 470nm before and after addition, F532Is VB2Fluorescence intensity at 532nm of the solution before and after addition.
Example 9
The nitrogen-doped carbon dots based on carnation flowers prepared in example 1 were examined for pH, as shown in fig. 6, by adding carbon quantum dot solutions to PBS buffer solutions of different pH, the carbon dots showed a change in fluorescence peak intensity at 470 nm. Working curve for pH detection based on nitrogen-doped carbon spots of carnation flowers (fig. 6 inset): in the pH range of 3.6-8, the fluorescence intensity F of the carbon point at 470nm has a good linear relation with the pH.
Example 10
Nitrogen-doped carbon dot aqueous solution based on carnation flower prepared in example 1 was used for VB in actual samples of commercial orange juice, soybean milk, honey, B-vitamin tablets and multi-vitamin complex tablets2The actual samples tested by adding table as shown in Table 1, the VB in commercial orange juice, soybean milk, honey, vitamin B tablets and vitamin C complex tablets was recovered2Original content and tabulated recovery.
TABLE 1
Example 11
Application test of carnation flower-based nitrogen-doped carbon dots prepared in example 1 in cell imaging:
the carnation flower-based nitrogen-doped carbon dot aqueous solution prepared in example 1 was used for labeling of cervical cancer cells Hela, e.g.FIG. 7 shows graphs of the first, second, third and fourth rows, respectively, of cervical cancer cells Hela marked by nitrogen-doped carbon dots based on carnation flowers, to which VB was added at 0, 11.9. mu.M, 23.8. mu.M and 35.9. mu.M2After incubation for 20 minutes, the cells are placed under a laser confocal microscope to observe the change of the fluorescence intensity in the cells, and the change is used for detecting the VB in the cells2. The photographs of the carbon dot-labeled cells at an excitation wavelength of 405nm are, from left to right: dark field (blue channel) cytogram, dark field (green channel) cytogram, and combined bright and dark field cytogram. (first, second and third series of fig. 7).
Example 12
The carnation flower-based nitrogen-doped carbon dots prepared in example 1 were used to mark the cervical cancer cells Hela, as shown in the first, second, and third line graphs of fig. 8, respectively, and the carnation flower-based nitrogen-doped carbon dot-marked cervical cancer cells Hela were incubated in PBS buffer solutions with pH of 3.6, 5.3, and 7.4 for 30 minutes, and then placed under a confocal laser microscope to observe the change in the fluorescence intensity inside the cells, for detecting the pH inside the cells. The photographs of the carbon dot-labeled cells at an excitation wavelength of 405nm are, from left to right: bright field cytograms, dark field (blue channel) cytograms, dark field (green channel) cytograms, and cytograms for bright and dark fields. (first, second and third series of fig. 7).
Claims (9)
1. A preparation method of nitrogen-doped carbon dots based on carnation flowers is characterized by comprising the following steps:
1) putting the dried carnation petals in a beaker, adding secondary water, adding polyethyleneimine into the solution, and performing ultrasonic treatment to obtain a mixed solution; the mass ratio of the dried carnation petals to the polyethyleneimine to the secondary water is 0.3-0.7: 0.3-0.7: 10-15 parts of;
2) placing the solution subjected to ultrasonic treatment in a high-pressure reaction kettle, carrying out hydrothermal reaction for 2-5h at the temperature of 120-170 ℃, then naturally cooling the high-pressure reaction kettle to room temperature, and filtering with filter paper to remove large particles in the solution after reaction; then, further filtering the dark brown filtrate by a cylindrical filter membrane filter (0.22 mu m) to obtain a nitrogen-doped carbon quantum dot aqueous solution of the carnation flower;
3) and (3) freeze-drying the carbon quantum dot aqueous solution to obtain the nitrogen-doped carbon dots based on the carnation flowers.
2. The method for preparing nitrogen-doped carbon dots based on carnation flowers as claimed in claim 1, wherein the mass ratio of the withered carnation petals, the polyethyleneimine and the secondary water in the step 1) is 0.5:0.5: 12.
3. The method for preparing nitrogen-doped carbon dots based on carnation flowers as claimed in claim 1, wherein the hydrothermal reaction temperature in the step 2) is 150 ℃ and the reaction time is 3 h.
4. The carnation flower based nitrogen doped carbon dots prepared by the method of claim 1, 2 or 3.
5. The carnation flower-based nitrogen-doped carbon dots according to claim 4, wherein VB is added to orange juice, soybean milk, honey, vitamin B tablets or multi-vitamin complex tablets2And (5) detecting the content.
6. The carnation flower-based nitrogen-doped carbon dots of claim 4 for preparing intracellular VB2Use in a sensing agent.
7. A fluorescent paint with pH-controlled color development, characterized by containing nitrogen-doped carbon dots based on carnation flowers as claimed in claim 4.
8. The method for preparing fluorescent paint with pH controlled color development according to claim 7, characterized by comprising the following steps: adding polyvinyl alcohol into secondary water, heating to fully dissolve the polyvinyl alcohol, adding an ethanol solution in which fluorane dye and epoxy resin are dissolved, fully stirring and mixing the mixture, cooling the mixture for 10 minutes, adding a nitrogen-doped carbon dot solution of carnation flowers into the mixture, fully stirring the mixture, and uniformly mixing the mixture to obtain the pH-controlled color-developable fluorescent paint.
9. The method for preparing fluorescent paint with pH controlled color development according to claim 8, wherein the mass ratio of nitrogen-doped carbon dots of the polyvinyl alcohol, the secondary water, the ethanol, the fluoran dye, the epoxy resin and the carnation flower is 2-4:20:5-8:0.05-0.1:0.02-0.05: 0.004-0.01.
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CN114891503A (en) * | 2022-06-06 | 2022-08-12 | 沈阳药科大学 | Poplar flower-based green carbon quantum dot fluorescent probe and preparation method and application thereof |
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