CN109337681B - Preparation method and application of sulfur-nitrogen co-doped carbon quantum dot - Google Patents
Preparation method and application of sulfur-nitrogen co-doped carbon quantum dot Download PDFInfo
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Abstract
The invention provides a preparation method of a sulfur-nitrogen co-doped carbon quantum dot, which comprises the following steps of mixing phenothiazine, sodium nitrite, dichloromethane and acetic acid, and carrying out nitration reaction to obtain 3, 7-dinitrophenothiazine; and mixing the 3, 7-dinitrophenothiazine and alkali liquor, and sequentially carrying out hydrothermal reaction and dialysis to obtain the sulfur-nitrogen co-doped carbon quantum dots. According to the invention, firstly, a nitrogen source and a sulfur source are nitrified to increase the nitrogen content of the carbon quantum dots, and then the obtained 3, 7-dinitrophenothiazine is mixed with alkali liquor to generate hydrothermal reaction, so that the sulfur-nitrogen doped carbon quantum dots are prepared. The content of nitrogen in the carbon quantum dots is 3.45-9.69 wt%, the content of sulfur in the carbon quantum dots is 0.51-0.83 wt%, and the carbon quantum dots have strong nonlinear scattering performance and very good optical limiting performance.
Description
Technical Field
The invention relates to the technical field of laser protection materials, in particular to a sulfur-nitrogen co-doped carbon quantum dot and a preparation method and application thereof.
Background
The carbon quantum dot is a dispersed fluorescent carbon nano-particle with the size of below 10nm in a sphere-like shape. Compared with other fluorescent nanoparticles, the carbon quantum dots have the advantages of good biocompatibility, easy surface functionalization and the like, and also have a plurality of excellent photophysical characteristics: excitation wavelength dependence, photostability, pH dependence, electrochemiluminescence, strong absorption in the ultraviolet region, and upconversion fluorescence properties. The excellent properties enable the carbon quantum dots to have important application values in the fields of biological detection, biological sensing, fluorescent probes, medicine, photocatalysis and the like.
In recent years, research on the optical limiting performance of carbon quantum dots is started, but how to prepare a sulfur-nitrogen co-doped carbon quantum dot with excellent optical limiting performance is not reported in the prior art.
Disclosure of Invention
The invention aims to provide a sulfur-nitrogen co-doped carbon quantum dot with excellent optical amplitude limiting performance.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a preparation method of a sulfur-nitrogen co-doped carbon quantum dot, which comprises the following steps:
mixing phenothiazine, sodium nitrite, dichloromethane and acetic acid, and carrying out nitration reaction to obtain 3, 7-dinitrophenothiazine;
and mixing the 3, 7-dinitrophenothiazine and alkali liquor, and sequentially carrying out hydrothermal reaction and dialysis to obtain the sulfur-nitrogen co-doped carbon quantum dots.
Preferably, the molar ratio of the phenothiazine to the sodium nitrite is 1: (5.5-6.5).
Preferably, the volume ratio of the phenothiazine substance to the dichloromethane is (0.08-0.12) mol: (180-220) mL.
Preferably, the volume ratio of the mass of the sodium nitrite to the acetic acid is (0.28-0.32) mol: (70-90) mL.
Preferably, the temperature of the nitration reaction is 20-50 ℃, and the time of the nitration reaction is 2-6 h.
Preferably, the alkali liquor is 0.2mol/L sodium hydroxide aqueous solution or 1mol/L ammonia water.
Preferably, the mass ratio of the 3, 7-dinitrophenothiazine to the alkali liquor is 1 g: (180-220) mL.
Preferably, the temperature of the hydrothermal reaction is 120-200 ℃, and the time of the hydrothermal reaction is 10-14 h.
Preferably, the cut-off molecular weight of the dialysis bag for dialysis is 500 to 1000.
The invention also provides application of the sulfur-nitrogen co-doped carbon quantum dot in laser protection.
The invention provides a preparation method of a sulfur-nitrogen co-doped carbon quantum dot, which comprises the following steps of mixing phenothiazine, sodium nitrite, dichloromethane and acetic acid, and carrying out nitration reaction to obtain 3, 7-dinitrophenothiazine; and mixing the 3, 7-dinitrophenothiazine and alkali liquor, and sequentially carrying out hydrothermal reaction and dialysis to obtain the sulfur-nitrogen co-doped carbon quantum dots. According to the invention, nitrogen content in the carbon quantum dots can be increased by firstly nitrifying a nitrogen source and a sulfur source, and then the obtained 3, 7-dinitrophenothiazine is mixed with alkali liquor to generate hydrothermal reaction, so that the sulfur-nitrogen doped carbon quantum dots are prepared. The content of nitrogen in the carbon quantum dots is 3.45-9.69 wt%, the content of sulfur in the carbon quantum dots is 0.51-0.83 wt%, and the carbon quantum dots have strong nonlinear scattering performance and very good optical limiting performance.
Drawings
FIG. 1 is an XPS energy spectrum of D-1 prepared in example 1 and D-2 prepared in example 2;
FIG. 2 is a graph of normalized luminescence intensity of D-1 prepared in example 1 at different ionic intensities;
FIG. 3 is a graph of normalized luminous intensity of D-1 prepared in example 1 under different times of UV irradiation;
FIG. 4 is a Z-scan of D-1 prepared in example 1 and D-2 prepared in example 2;
FIG. 5 is a graph showing the nonlinear scattering curves of D-1 prepared in example 1 and D-2 prepared in example 2;
FIG. 6 is a graph of the optical clipping performance of D-1 prepared in example 1 and D-2 prepared in example 2;
FIG. 7 is a graph of normalized luminescence intensity of D-2 prepared in example 2 at different ionic intensities;
FIG. 8 is a graph of normalized luminous intensity of D-2 prepared in example 2 under different times of UV irradiation.
Detailed Description
The invention provides a preparation method of a sulfur-nitrogen co-doped carbon quantum dot, which comprises the following steps:
mixing phenothiazine, sodium nitrite, dichloromethane and acetic acid, and carrying out nitration reaction to obtain 3, 7-dinitrophenothiazine;
and mixing the 3, 7-dinitrophenothiazine and alkali liquor, and sequentially carrying out hydrothermal reaction and dialysis to obtain the sulfur-nitrogen co-doped carbon quantum dots.
In the present invention, all the raw material components are commercially available products well known to those skilled in the art unless otherwise specified.
The method mixes phenothiazine, sodium nitrite, dichloromethane and acetic acid to carry out nitration reaction, and obtains the 3, 7-dinitrophenothiazine. In the invention, the phenothiazine is used as a nitrogen source and a sulfur source at the same time; the sodium nitrite is a nitrogen source; the dichloromethane is a solvent of phenothiazine; the acetic acid is a solvent for sodium nitrite.
In the present invention, the molar ratio of phenothiazine to sodium nitrite is preferably 1: (5.5 to 6.5), more preferably 1: (5.8-6.2). In the present invention, the volume ratio of the amount of phenothiazine to methylene chloride is preferably (0.08 to 0.12) mol: (180 to 220) mL, more preferably (0.09 to 0.11) mol: (190-210) mL. In the present invention, the volume ratio of the mass of sodium nitrite to acetic acid is preferably (0.28 to 0.32) mol: (70 to 90) mL, more preferably (0.29 to 0.31) mol: (75-85) mL.
In the invention, the temperature of the nitration reaction is preferably 20-50 ℃, more preferably 30-40 ℃, and most preferably 34-36 ℃; the time of the nitration reaction is preferably 2-6 h, more preferably 2.5-5 h, and most preferably 3-4 h.
In the present invention, the nitration reaction is preferably carried out under stirring conditions; the stirring conditions in the present invention are not particularly limited, and the stirring conditions known to those skilled in the art may be employed.
In the present invention, the specific process of the nitration reaction is preferably:
under the condition of stirring, slowly adding 50% of sodium nitrite into a mixed solution of phenothiazine, 50% of dichloromethane and 50% of acetic acid to carry out nitration reaction I;
and (3) continuously adding 50% of dichloromethane, 50% of acetic acid and 50% of sodium nitrite into the reaction system to perform nitration reaction II.
In the invention, the ratio of the time of the nitration reaction I to the time of the nitration reaction II is preferably (0.5-1.5) h: (1-3) h, more preferably (0.6-1.4): (1.4-2.6) h, most preferably (0.8-1.2): (1.6-2.4) h.
In the invention, the nitration reaction is carried out step by step, so that the nitration reaction at the 3 and 7 positions of the phenothiazine can be promoted to be more sufficient.
After the nitration reaction is finished, the invention preferably carries out post-treatment on a product system obtained by the nitration reaction to obtain 3, 7-dinitrophenothiazine; in the present invention, the post-treatment preferably comprises:
mixing a product system obtained by nitration reaction with an acetic acid solution, and sequentially performing suction filtration and washing to obtain a crude product;
and (3) mixing the crude product with DMF at 100 ℃, filtering while the crude product is hot, washing and drying to obtain the 3, 7-dinitrophenothiazine.
The method mixes a product system obtained by nitration reaction with an acetic acid solution, and sequentially performs suction filtration and washing to obtain a crude product. In the invention, the mass concentration of the acetic acid solution is preferably 90-100%, and more preferably 95-98%; the ratio of the total volume of dichloromethane and acetic acid to the volume of the acetic acid solution is preferably 3: (1.5-5), more preferably 3: (2-4). In the invention, the acetic acid solution is used for further removing sodium nitrite which does not participate in the reaction in a product system obtained by the nitration reaction.
In the present invention, the mixing is preferably performed under stirring; in the invention, the stirring time is preferably 1.5-2.5 h, and more preferably 1.8-2.2 h; the stirring rate is not particularly limited in the present invention, and the stirring may be performed at a stirring rate known to those skilled in the art.
The suction filtration is not limited in any way, and can be performed by adopting a suction filtration process well known to those skilled in the art.
In the present invention, the washing is preferably three times with ethanol and water in this order.
After a crude product is obtained, the crude product is mixed with DMF at 100 ℃, and the mixture is filtered, washed and dried while being hot to obtain the 3, 7-dinitrophenothiazine. The amount of DMF used in the invention is not particularly limited, and may be any amount known to those skilled in the art; in the invention, DMF is used for further removing phenothiazine which does not participate in the reaction in a product system obtained by the nitration reaction.
The filtration is not particularly limited in the present invention, and may be carried out under filtration conditions known to those skilled in the art.
In the present invention, the washing detergent is preferably ethanol; the specific washing process is not particularly limited, and washing may be performed by a washing process known to those skilled in the art.
The drying process is not particularly limited, and may be a drying process known to those skilled in the art.
After the 3, 7-dinitrophenothiazine is obtained, the 3, 7-dinitrophenothiazine and alkali liquor are mixed, and then hydrothermal reaction and dialysis are sequentially carried out, so that the sulfur-nitrogen co-doped carbon quantum dot is obtained. In the present invention, the alkali solution is preferably 0.2mol/L aqueous sodium hydroxide solution or 1mol/L aqueous ammonia. In the invention, the ratio of the mass of the 3, 7-dinitrophenothiazine to the volume of the alkali liquor is preferably 1 g: (180-220) mL, more preferably 1 g: (190-210) mL. In the invention, the mixing time is preferably 1.5-2.5 h, and more preferably 1.8-2.2 h. In the present invention, the mixing is preferably performed under the condition of ultrasound; the present invention does not have any particular limitation on the rate of the ultrasound, and may be performed using an ultrasound rate well known to those skilled in the art.
In the invention, the temperature of the hydrothermal reaction is preferably 120-200 ℃, more preferably 140-180 ℃, and most preferably 160-170 ℃; the time of the hydrothermal reaction is preferably 10-14 h, and more preferably 12-13 h.
In the invention, after the hydrothermal reaction is finished, the obtained product system is preferably sequentially cooled and filtered; in the present invention, the cooling is preferably natural cooling to room temperature; in the present invention, the filtration is preferably carried out by passing the product system through a filter membrane having a pore size of 0.22 μm to remove large particles of water-insoluble carbon material and a portion of unreacted starting material.
In the present invention, the cut-off molecular weight of the dialysis bag for dialysis is preferably 500 to 1000, more preferably 600 to 800.
In the present invention, the purpose of the dialysis is to remove sodium salts and small molecules without carbonization.
After the dialysis is finished, the invention preferably dries the solid substance obtained after the dialysis; in the present invention, the drying is preferably vacuum drying; the temperature of the vacuum drying is preferably 40-60 ℃, and more preferably 45-55 ℃; the vacuum drying time is preferably 20-30 h, more preferably 22-28 h, and most preferably 24-26 h.
The invention also provides the sulfur-nitrogen co-doped carbon quantum dot prepared by the preparation method, wherein the nitrogen content in the sulfur-nitrogen co-doped carbon quantum dot is 3.45-9.69 wt%, and the sulfur content is 0.51-0.83 wt%.
The invention also provides application of the sulfur-nitrogen co-doped carbon quantum dot in laser protection.
The sulfur and nitrogen doped carbon quantum dots provided by the present invention, the preparation method and the application thereof are described in detail with reference to the following examples, but they should not be construed as limiting the scope of the present invention.
Example 1
Synthesis of 3, 7-dinitrophenothiazine:
under the condition of stirring, 20.00g of sodium nitrite (300mmol) is slowly added into a mixture of 20.00g of phenothiazine (100mmol), 100mL of dichloromethane and 40mL of acetic acid, after the mixture is stirred for 1 hour at room temperature, 100mL of dichloromethane, 40mL of acetic acid and 20.00g of sodium nitrite are added, the reaction lasts for 1.5 hours, and a large amount of solid is generated; and adding 120mL of acetic acid diluted solution into the system, continuously stirring for 2 hours, performing suction filtration, and washing with ethanol and water for three times. Then dissolving the obtained solid in DMF at 100 ℃, filtering while hot, using a filter cake as a product, washing with ethanolThe filter cake was washed and dried to give a magenta color of 3, 7-dinitrophenothiazine (86% yield).1HNMR(400MHz；DMSO-d6)：6.69(d，J＝4Hz,2H)，7.70(s，2H)，7.82(d，J＝4Hz，2H)。HRMS(ESI)m/zC12H8N3O4S+(M+H)+Calculated values: 290.0230, found: 290.0245. calculated values of elemental analysis: c, 49.83; h, 2.44; n, 14.53; measured value: c, 49.95; h, 2.51; n, 14.61.
And (3) synthesizing a sulfur-nitrogen co-doped carbon quantum dot:
3, 7-dinitrophenothiazine (0.3g) was dispersed in 60mL of a 0.2mol/L aqueous solution of sodium hydroxide under ultrasonic conditions, and ultrasonic treatment was performed for 2 hours to obtain a suspension, which was then reacted at 200 ℃ for 12 hours. After the reaction, the reaction mixture was cooled to room temperature, and the reaction mixture was filtered through a filter having a pore size of 0.22 μm to remove large particles of a water-insoluble carbon material and a part of unreacted raw materials. And concentrating the filtrate, dialyzing by using a dialysis bag with the molecular weight cutoff of 500-1000, removing sodium salt and small molecules without carbonization, and drying in vacuum to obtain the sulfur and nitrogen doped carbon quantum dots, which are recorded as D-1. D-1 is approximately spherical, the distribution range of the particle size is 1.5-4.5 nm, and the average particle size is 2.8 nm;
FIG. 2 is a graph of normalized luminescence intensity of D-1 under different ionic intensities, from which it can be seen that the fluorescence emission intensity of the quantum dot does not decrease with the increase of the ionic intensity of the solution, and has good ionic strength resistance;
FIG. 3 is a graph showing normalized emission intensity of D-1 under different irradiation times with an ultraviolet lamp, and it can be seen that the fluorescence intensity slightly decreases with the increase of the irradiation time, showing excellent light stability.
Example 2
Synthesis of 3, 7-dinitrophenothiazine reference example 1;
and (3) synthesizing a sulfur-nitrogen co-doped carbon quantum dot:
0.3g of 3, 7-dinitrophenothiazine is dispersed in 60mL of 1mol/L ammonia water solution under the condition of ultrasound, the solution is kept for 2 hours to obtain a suspension, and the suspension is reacted for 12 hours at 200 ℃. After the reaction, the reaction mixture was cooled to room temperature, and the reaction mixture was filtered through a filter having a pore size of 0.22 μm to remove large particles of a water-insoluble carbon material and a part of unreacted raw materials. And (3) concentrating the filtrate, dialyzing by using a dialysis bag with the molecular weight cut-off of 500-1000, removing sodium salt and small molecules without carbonization, and drying in vacuum to obtain the carbon quantum dot doped with sulfur and nitrogen, which is recorded as D-2. The shape of the D-2 is approximately spherical, the distribution range of the particle size is 1.5-4 nm, and the average particle size is 3.1 nm;
FIG. 7 is a graph of normalized luminescence intensity of D-2 under different ionic intensities, from which it can be seen that the fluorescence emission intensity of the quantum dots does not decrease with the increase of the ionic intensity of the solution, and has good ionic intensity resistance performance;
FIG. 8 is a graph of normalized emission intensity of D-2 under different irradiation times with UV lamps, showing that the fluorescence intensity decreases only slightly with increasing irradiation time, showing excellent light stability;
FIG. 1 shows XPS spectra of D-1 and D-2, wherein D-1 is mainly composed of C, O, N and S, and the weight ratio of C: o: n: s-55.34%: 36.15%: 3.45%: 0.83%, wherein the nitrogen is present in the form of pyridine nitrogen atom, amino nitrogen atom and pyrrole nitrogen atom; sulfur mainly represented by S2P3/2C-S-C and S of2P1/2The C-S-C form of (A); d-2 is mainly composed of C, O, N and S, and the weight ratio of the four elements is calculated as C: o: n: s58.59%: 26.39%: 9.69%: 0.51% of nitrogen, wherein the nitrogen is present in the form of pyridine nitrogen atom, amino nitrogen atom and pyrrole nitrogen atom; sulfur mainly represented by S2P3/2C-S-C and S of2P1/2The C-S-C form of (A);
FIG. 4 is a Z-scan of D-1 and D-2, showing that the intensity of the light beam transmitted through the sample increases and the optical limiting effect increases as the sample is closer to the focal point, and D-1 is dispersed in DMF by ultrasonic treatment for 30min in DMF solution, and the transmittance is maintained at 70% at 532 nm. Under 532nm laser with 4ns pulse, when the sample approaches the focus, the transmittance of D-1 gradually decreases and decreases to 72% at the focus because the laser energy is maximum at the focus, and D-2 is dispersed by ultrasonic treatment in DMF for 30min, and the transmittance is maintained at 70% at 532 nm. Under 532nm laser with 4ns pulse, when a sample approaches a focus, the transmittance of D-1 is gradually reduced and reduced to 64% at the focus because the laser energy at the focus is the largest;
FIG. 5 is a graph of the nonlinear scattering curves of D-1 and D-2, and it can be seen that both D-1 and D-2 exhibit certain scattering responses, and can be used as good nonlinear scatterers and effective light-limiting materials;
FIG. 6 is a graph showing the optical clipping performance of D-1 and D-2, and it can be seen that both D-1 and D-2 have very good optical clipping performance at a wavelength of 532 nm.
From the above embodiments, it can be known that the sulfur-nitrogen co-doped carbon quantum dot prepared by the preparation method of the present invention has a very good optical limiting effect.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (9)
1. A preparation method of a sulfur-nitrogen co-doped carbon quantum dot comprises the following steps:
mixing phenothiazine, sodium nitrite, dichloromethane and acetic acid, and carrying out nitration reaction to obtain 3, 7-dinitrophenothiazine;
mixing the 3, 7-dinitrophenothiazine and alkali liquor, and sequentially carrying out hydrothermal reaction and dialysis to obtain sulfur-nitrogen co-doped carbon quantum dots;
the alkali liquor is 0.2mol/L sodium hydroxide aqueous solution or 1mol/L ammonia water.
2. The method according to claim 1, wherein the molar ratio of phenothiazine to sodium nitrite is 1: (5.5-6.5).
3. The method according to claim 1, wherein the volume ratio of the amount of phenothiazine substance to methylene chloride is (0.08 to 0.12) mol: (180-220) mL.
4. The method according to claim 1, wherein the volume ratio of the mass of sodium nitrite to acetic acid is (0.28 to 0.32) mol: (70-90) mL.
5. The preparation method according to claim 1, wherein the temperature of the nitration reaction is 20 to 50 ℃ and the time of the nitration reaction is 2 to 6 hours.
6. The method according to claim 1, wherein the ratio of the mass of the 3, 7-dinitrophenothiazine to the volume of the alkali solution is 1 g: (180-220) mL.
7. The method according to claim 1, wherein the hydrothermal reaction is carried out at a temperature of 120 to 200 ℃ for 10 to 14 hours.
8. The method according to claim 1, wherein the dialysis bag for dialysis has a molecular weight cut-off of 500 to 1000.
9. The application of the sulfur-nitrogen co-doped carbon quantum dot prepared by the preparation method of any one of claims 1 to 8 in laser protection.
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