CN108485662A - Nitrogen, sulphur codope fluorescent carbon quantum dot material and preparation method thereof - Google Patents
Nitrogen, sulphur codope fluorescent carbon quantum dot material and preparation method thereof Download PDFInfo
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Abstract
The present invention disclose a kind of nitrogen, sulphur codope fluorescent carbon quantum dot material and preparation method thereof, the preparation method includes the following steps：1）Citric acid and N acetyl L cysteine solids are weighed, is placed in beaker, mixing, 150 ~ 250 DEG C is heated to electric jacket；2）Hybrid solid gradually melts, and color becomes light yellow from colourless, eventually becomes brown, after heating 20 ~ 30min, rapidly pours into the solution of melting in ultra-pure water, and be constantly vigorously stirred；3）Then it is dialysed in deionized water 20 ~ 30 hours with 100 ~ 500D cellulose dialysis bag, it is 4.0 ~ 6.0 to use 1M NaOH to adjust pH later.To gained quantum point carry out vacuum freeze drying, with ultrapure water dissolution obtain nitrogen, sulphur codope fluorescent carbon quantum dot aqueous solution.The advantages that present invention is easy to get with raw material, environmentally protective, hypotoxicity, and the fluorescent carbon quantum dot good dispersion of gained, epigranular, with good stability and higher fluorescence quantum yield.
Description
Technical field
The present invention relates to the preparation methods of a kind of nitrogen, the fluorescent carbon quantum dot material of sulphur codope, belong to nanotechnology neck
Domain.
Background technology
Carbon quantum dot（Carbon quantum dots, CQDs）It is that grain size is glimmering less than environmentally friendly one kind of 10 nm
Light nano material, is mainly made of carbon, does not contain heavy metal element, and it is excellent to have that biocompatibility is high, cytotoxicity is low etc.
Point, it is small to the interference of biomolecule, it is expected to be applied to optical imagery, biomedicine and analysis inspection instead of traditional quantum dot
Survey field.
In recent years, scientists, which wish to find, prepares the more cheap method of relatively simple, cost to carry out processability excellent
And the carbon quantum dot of high-fluorescence quantum yield, and it is applied to the fields such as medicine, life science, photoelectricity.Research table recently
The grain size of bright carbon quantum dot has vital influence with surface characteristics on its property.The carbon quantum dot specific surface area of small particle
Greatly, surface light emitting site is also more.Therefore the carbon quantum dot of small particle, which shines, is better than large-sized carbon quantum dot, further demonstrates that
It is relevant with surface that carbon quantum dot, which shines,.In addition, a large amount of oxygen-containing groups are contained such as in surface（Hydroxyl, carboxyl etc.）Carbon quantum dot
With good water solubility and it is easily achieved further functionalization.Therefore, fluorescent carbon quantum dot has unique physics and chemistry
Property has broad application prospects in magnetics, electricity, optics, catalysis and chemical sensitisation and biomedicine etc..
Many performances of carbon quantum dot depend primarily on selected synthesis material, the internal structure of nano material and surface
Activity, wherein surface-active are to determine the principal element of carbon quantum dot performance.And carbon quantum dot functionalization is for improving carbon amounts
The best approach of son point performance, is presently mainly realized by two methods of surface modification and doped chemical.In semiconductor die
Mixed in lattice impurity to the light of semiconductor-quantum-point, electrically and magnetically and other physical properties generate strong influence.
The present invention can provide the citric acid of carbon, nitrogen, element sulphur simultaneously（CA）And N-acetyl-L-cysteine（L-Cys）
For synthesize presoma, using simple one step hydro thermal method prepare water-soluble nitrogen, sulphur codope fluorescent carbon quantum dot.
Invention content
The purpose of the present invention is to provide a kind of nitrogen, the fluorescent carbon quantum dot materials and preparation method thereof of sulphur codope.This
The synthetic technology provided is invented, simple for process, synthesis presoma only needs two kinds of small-molecule substances, at low cost, is suitable for extensive batch
Amount production.
To achieve the goals above, the present invention using pyrolysismethod prepare the uniform nitrogen of particle diameter distribution, sulphur codope it is glimmering
Light carbon quantum dot, technical solution are that fluorescence carbon amounts is made through pyrolysismethod in citric acid and N-acetyl-L-cysteine solid powder
Sub- point.A kind of nitrogen of the present invention, sulphur codope fluorescent carbon quantum dot material preparation method, include the following steps：1）
Weigh citric acid and N-acetyl-L-cysteine, the mass ratio 1 of citric acid and N-acetyl-L-cysteine:1-1.4 being placed in burning
In cup, mixing is heated to 150 ~ 250 DEG C with electric jacket； 2）Hybrid solid gradually melts, and color becomes light yellow from colourless, most
After become brown, after heating 20 ~ 30min, the solution of melting is poured into ultra-pure water rapidly, and is constantly vigorously stirred, obtains heat
Solve product；3）By step 2）The thermal decomposition product of acquisition is dialysed 20 ~ 30 small in deionized water with 100-500D cellulose dialysis bag
When, later with NaOH adjust pH be 4.0 ~ 6.0, to gained quantum point carry out vacuum freeze drying, with ultrapure water dissolution obtain nitrogen,
The fluorescent carbon quantum dot aqueous solution of sulphur codope.
The fluorescent carbon quantum dot aqueous solution acquires fluorescent carbon quantum dot solid powder after rotating, being dried in vacuo, glimmering
Light carbon quantum dot average grain diameter is 3.82 nm.
By step 2）The thermal decomposition product of acquisition is dialysed 24 hours in deionized water with 100-500D cellulose dialysis bag, the phase
Between every 4 hours replace extracellular fluid dialysis.
PH is adjusted with 1M NaOH after dialysis, vacuum freeze drying is carried out to gained quantum point, dissolves quantum with ultra-pure water
Point aqueous solution.
Nitrogen made from the above-mentioned preparation method of the present invention, sulphur codope fluorescent carbon quantum dot, 4 DEG C be kept in dark place it is spare.
Above-mentioned fluorescent carbon quantum dot material aqueous solution is in amber transparent shape, when the ultraviolet-visible absorption spectroscopy for scanning the solution
The absorption maximum peak position of fluorescent carbon quantum dot solution is at 337nm afterwards.
Above-mentioned fluorescent carbon quantum dot average grain diameter is 3.82 nm.
Specifically, nitrogen of the present invention, sulphur codope fluorescent carbon quantum dot preparation method, including walk as follows
Suddenly：1）Citric acid and N-acetyl-L-cysteine solid are weighed, is placed in beaker, mixing is heated to 200 DEG C with electric jacket；
2）Hybrid solid gradually melts, and color becomes light yellow from colourless, eventually becomes brown, after heating 25min, rapidly by melting
Solution pours into ultra-pure water, and is constantly vigorously stirred；3）Then it is dialysed in deionized water with 100-500D cellulose dialysis bag
24 hours, it was 5.0 to use 1M NaOH to adjust pH later.Vacuum freeze drying is carried out to gained quantum point, is obtained with ultrapure water dissolution
Nitrogen, sulphur codope fluorescent carbon quantum dot aqueous solution.
The fluorescent carbon quantum dot aqueous solution acquires fluorescent carbon quantum dot solid powder, institute after rotating, being dried in vacuo
It is 3.82 nm to state fluorescent carbon quantum dot average grain diameter.
The preparation method of the fluorescent carbon quantum dot material of the nitrogen, sulphur codope, it is characterised in that
1）Citric acid and N-acetyl-L-cysteine solid are weighed, is placed in 10mL beakers, mixing, 200 are heated to electric jacket
℃；
2）By step 1）The hybrid solid of acquisition gradually melts, and color becomes light yellow from colourless, eventually becomes brown；
3）After heating 25min, the solution of melting is poured into ultra-pure water rapidly, and is constantly vigorously stirred, obtains thermal decomposition product；
4）By step 3）The thermal decomposition product of acquisition is dialysed 24 hours in deionized water with 100-500D cellulose dialysis bag, during which
Replace extracellular fluid dialysis within every 4 hours；
5）It is 5.0 to adjust pH with 1M NaOH after dialysis.Vacuum freeze drying is carried out to gained quantum point, with ultrapure water dissolution
Obtain nitrogen, sulphur codope fluorescent carbon quantum dot aqueous solution, 4 DEG C be kept in dark place it is spare.
Step 1）In electric jacket heating temperature be preferably 200 DEG C, hybrid solid gradually melts, and color is by no discoloration
It is light yellow, eventually becomes brown, the time for continuing pyrolysis later is preferably 25min.
Nitrogen made from the above-mentioned preparation method of the present invention, sulphur codope fluorescent carbon quantum dot.
The fluorescent carbon quantum dot of the nitrogen, sulphur codope, it is characterised in that fluorescent carbon quantum dot material aqueous solution is in palm fibre
Color transparence, the absorption maximum peak position of fluorescent carbon quantum dot solution exists after scanning the ultraviolet-visible absorption spectroscopy of the solution
At 337nm.
The fluorescent carbon quantum dot of the nitrogen, sulphur codope, it is characterised in that fluorescent carbon quantum dot average grain diameter is 3.82
nm。
Specifically, nitrogen of the present invention, sulphur codope fluorescent carbon quantum dot preparation method, method and step
For：
Step 1：Citric acid and N-acetyl-L-cysteine solid are weighed, is placed in beaker, mixing is heated to 200 with electric jacket
℃；
Step 2：By step 1）The hybrid solid of acquisition gradually melts, and color becomes light yellow from colourless, eventually becomes brown；
Step 3：After heating 25min, the solution of melting is poured into ultra-pure water rapidly, and is constantly vigorously stirred, obtains pyrolysis production
Object；
Step 4：By step 3）The thermal decomposition product of acquisition is dialysed 24 hours in deionized water with 100-500D cellulose dialysis bag,
Every 4 hours of period replaced extracellular fluid dialysis；
Step 5：It is 5.0 to adjust pH with 1M NaOH after dialysis.Vacuum freeze drying is carried out to gained quantum point, uses ultra-pure water
Dissolving obtain nitrogen, sulphur codope fluorescent carbon quantum dot aqueous solution, 4 DEG C be kept in dark place it is spare.
The presoma citric acid and N-acetyl-L-cysteine without doing any pretreatment, in reaction process in addition to
Presoma citric acid and N-acetyl-L-cysteine is added it is not necessary that any other reagent is added.
Obtained nitrogen, sulphur codope fluorescent carbon quantum dot average grain diameter be 3.82 nm.
It is an advantage of the invention that：In addition to being added during the fluorescent carbon quantum dot material preparation of the nitrogen, sulphur codope
Presoma citric acid and N-acetyl-L-cysteine are without being added any other reagent.By presoma citric acid and N- acetyl-
L-cysteine by simple step pyrolysismethod can be obtained nitrogen, sulphur codope fluorescent carbon quantum dot.Utilize present invention side
Method prepares simple process and low cost, environmentally protective.The fluorescent carbon quantum dot pattern rule of prepared nitrogen, sulphur codope, granularity
Uniformly, good water solubility, stability of solution is high, is easy to store, and is convenient for large-scale mass production.
Description of the drawings
Fig. 1 be nitrogen, sulphur codope photo of the fluorescent carbon quantum dot material aqueous solution under 365 nm ultra violet lamps,
Blue-fluorescence can be observed.
Fig. 2 be nitrogen, sulphur codope fluorescent carbon quantum dot material ultraviolet-visible absorption spectroscopy figure.
Fig. 3 is nitrogen, the fluorescence excitation of fluorescent carbon quantum dot material of sulphur codope, launching light spectrogram.
Fig. 4 be nitrogen, sulphur codope fluorescent carbon quantum dot material transmission electron microscope picture.
Fig. 5 be nitrogen, sulphur codope fluorescent carbon quantum dot material X X-ray photoelectron spectroscopy X figures.
Fig. 6 be nitrogen, sulphur codope fluorescent carbon quantum dot material infrared spectrogram.
Fig. 7 is linear graph of the area integral to absorbance value of emission spectrum.
Specific implementation mode
The present invention is further elaborated in the following with reference to the drawings and specific embodiments, and the present invention is not limited thereto.
Embodiment 1
（1）1.0001g citric acids and 1.0003g N-acetyl-L-cysteine solids accurately are weighed, is placed in 10mL beakers, is mixed
It is even, it is heated to 200 DEG C with electric jacket；
（2）The hybrid solid of above-mentioned acquisition is gradually melted, color becomes light yellow from colourless, eventually becomes brown；
（3）After heating 25min, the solution of melting is poured into 70mL ultra-pure waters rapidly, and is constantly vigorously stirred, obtains pyrolysis production
Object；
（4）By step（3）The thermal decomposition product of acquisition is dialysed 24 hours in deionized water with 100-500D cellulose dialysis bag, the phase
Between every 4 hours replace extracellular fluid dialysis；
（5）It is 5.0 to adjust pH with 1M NaOH after dialysis.Vacuum freeze drying is carried out to gained quantum point, with ultrapure water dissolution
Obtain the nitrogen of a concentration of 1.65mg/mL, the fluorescent carbon quantum dot aqueous solution of sulphur codope.The solution is in 365 nm ultra violet lamps
Under photo, blue-fluorescence can be observed（See Fig. 1）.It takes the solution to be diluted to a certain concentration on a small quantity, scans the suction of its UV, visible light
Receive spectrum, nitrogen, sulphur codope fluorescent carbon quantum dot solution absorption maximum peak position in 337 nm（See Fig. 2）.
Embodiment 2
（1）1.0001g citric acids and 1.0003g N-acetyl-L-cysteine solids accurately are weighed, is placed in 10mL beakers, is mixed
It is even, it is heated to 200 DEG C with electric jacket；
（2）The hybrid solid of above-mentioned acquisition is gradually melted, color becomes light yellow from colourless, eventually becomes brown；
（3）After heating 25min, the solution of melting is poured into 70mL ultra-pure waters rapidly, and is constantly vigorously stirred, obtains pyrolysis production
Object；
（4）By step（3）The thermal decomposition product of acquisition is dialysed 24 hours in deionized water with 100-500D cellulose dialysis bag, the phase
Between every 4 hours replace extracellular fluid dialysis；
（5）It is 5.0 to adjust pH with 1M NaOH after dialysis.Vacuum freeze drying is carried out to gained quantum point, with ultrapure water dissolution
Obtain the nitrogen of a concentration of 1.65mg/mL, the fluorescent carbon quantum dot aqueous solution of sulphur codope.A small amount of solution is taken to be diluted to certain dense
Degree, scans its excitation spectrum and emission spectrum, the maximum excitation wavelength of carbon quantum dot solution and best transmitted wave known to collection of illustrative plates
Long is respectively 346 nm and 418 nm（See Fig. 3）.
Embodiment 3
（1）1.0001g citric acids and 1.0003g N-acetyl-L-cysteine solids accurately are weighed, is placed in 10mL beakers, is mixed
It is even, it is heated to 200 DEG C with electric jacket；
（2）The hybrid solid of above-mentioned acquisition is gradually melted, color becomes light yellow from colourless, eventually becomes brown；
（3）After heating 25min, the solution of melting is poured into 70mL ultra-pure waters rapidly, and is constantly vigorously stirred, obtains pyrolysis production
Object；
（4）By step（3）The thermal decomposition product of acquisition is dialysed 24 hours in deionized water with 100-500D cellulose dialysis bag, the phase
Between every 4 hours replace extracellular fluid dialysis；
（5）It is 5.0 to adjust pH with 1M NaOH after dialysis.Vacuum freeze drying is carried out to gained quantum point, with ultrapure water dissolution
Obtain the nitrogen of a concentration of 1.65mg/mL, the fluorescent carbon quantum dot aqueous solution of sulphur codope.Acquired solution drop coating is enterprising in copper mesh
Row transmission electron microscope detect, nitrogen, sulphur codope fluorescent carbon quantum dot in rule monodisperse spherical, average grain diameter be 3.26 nm
（See Fig. 4）.
Embodiment 4
（1）1.0001g citric acids and 1.0003g N-acetyl-L-cysteine solids accurately are weighed, is placed in 10mL beakers, is mixed
It is even, it is heated to 200 DEG C with electric jacket；
（2）The hybrid solid of above-mentioned acquisition is gradually melted, color becomes light yellow from colourless, eventually becomes brown；
（3）After heating 25min, the solution of melting is poured into 70mL ultra-pure waters rapidly, and is constantly vigorously stirred, obtains pyrolysis production
Object；
（4）By step（3）The thermal decomposition product of acquisition is dialysed 24 hours in deionized water with 100-500D cellulose dialysis bag, the phase
Between every 4 hours replace extracellular fluid dialysis；
（5）It is 5.0 to adjust pH with 1M NaOH after dialysis.Vacuum freeze drying is carried out to gained quantum point, with ultrapure water dissolution
Obtain the nitrogen of a concentration of 1.65mg/mL, the fluorescent carbon quantum dot aqueous solution of sulphur codope.It can be obtained after rotating, being dried in vacuo
To nitrogen, the fluorescent carbon quantum dot solid powder of sulphur codope.Gained powder is taken to carry out X X-ray photoelectron spectroscopy X measurement, by collection of illustrative plates
Understand that a large amount of C, O, N, S element is contained on carbon quantum dot surface（See Fig. 5）.
Embodiment 5
（1）1.0001g citric acids and 1.0003g N-acetyl-L-cysteine solids accurately are weighed, is placed in 10mL beakers, is mixed
It is even, it is heated to 200 DEG C with electric jacket；
（2）The hybrid solid of above-mentioned acquisition is gradually melted, color becomes light yellow from colourless, eventually becomes brown；
（3）After heating 25min, the solution of melting is poured into 70mL ultra-pure waters rapidly, and is constantly vigorously stirred, obtains pyrolysis production
Object；
（4）By step（3）The thermal decomposition product of acquisition is dialysed 24 hours in deionized water with 100-500D cellulose dialysis bag, the phase
Between every 4 hours replace extracellular fluid dialysis；
（5）It is 5.0 to adjust pH with 1M NaOH after dialysis.Vacuum freeze drying is carried out to gained quantum point, with ultrapure water dissolution
Obtain the nitrogen of a concentration of 1.65mg/mL, the fluorescent carbon quantum dot aqueous solution of sulphur codope.It can be obtained after rotating, being dried in vacuo
To nitrogen, the fluorescent carbon quantum dot solid powder of sulphur codope.Gained powder is taken to carry out Fourier transform infrared（FTIR）Spectrum is surveyed
It is fixed, further demonstrate oxygen-containing group（O-H ,-COO-, C=O）And the presence of C-S, C=C and C-N（See Fig. 6）.
Embodiment 6
（1）1.0001g citric acids and 1.0003g N-acetyl-L-cysteine solids accurately are weighed, is placed in 10mL beakers, is mixed
It is even, it is heated to 200 DEG C with electric jacket；
（2）The hybrid solid of above-mentioned acquisition is gradually melted, color becomes light yellow from colourless, eventually becomes brown；
（3）After heating 25min, the solution of melting is poured into 70mL ultra-pure waters rapidly, and is constantly vigorously stirred, obtains pyrolysis production
Object；
（4）By step（3）The thermal decomposition product of acquisition is dialysed 24 hours in deionized water with 100-500D cellulose dialysis bag, the phase
Between every 4 hours replace extracellular fluid dialysis；
（5）It is 5.0 to adjust pH with 1M NaOH after dialysis.Vacuum freeze drying is carried out to gained quantum point, with ultrapure water dissolution
Obtain the nitrogen of a concentration of 1.65mg/mL, the fluorescent carbon quantum dot aqueous solution of sulphur codope.To be dissolved in 0.1M H2SO4Sulfuric acid
Quinine is as object of reference（345nm is excitation wavelength, and absorbance is chosen at 360nm, QY=0.54）, various concentration is measured respectively
N, S-CDs and the quinine sulfate emission spectrum of gained and ultra-violet absorption spectrum of respective concentration under the excitation of 346nm wavelength, then
Using the absorbance value at 360nm in the correspondence absorption spectrum under same concentration as X-axis, the area integral of emission spectrum is made for Y-axis
Figure, calculates the slope of a curve, further according to equation：
Φx = ΦST (mx / mST) (ηx2 /ηST2 )
Relative fluorescence quantum yield is calculated, " Φ " indicates that fluorescence quantum yield, " m " indicate the area integral pair of emission spectrum in formula
Absorbance value map curve obtained slope, " η " be solvent refraction index (wherein the refraction index of quinine sulfate be 1.33,
1.33) it is that " ST ", " X " indicate standard and sample solution respectively that carbon dots, which are dissolved in the refraction index in ultra-pure water,.As a result such as Fig. 7
It is shown, N is calculated to obtain, the relative fluorescence quantum yield of S-CDs is 74.08%.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all essences in the present invention
Any modification made by within refreshing and principle, equivalent replacement and improvement etc., should all be included in the protection scope of the present invention.
Claims (7)
1. a kind of nitrogen, sulphur codope fluorescent carbon quantum dot material preparation method, include the following steps：1）Weigh citric acid and
The mass ratio 1 of N-acetyl-L-cysteine, citric acid and N-acetyl-L-cysteine:1-1.4 is placed in beaker, mixing, is used
Electric jacket is heated to 150 ~ 250 DEG C； 2）Hybrid solid gradually melts, and color becomes light yellow from colourless, eventually becomes brown,
After heating 20 ~ 30min, the solution of melting is poured into ultra-pure water rapidly, and is constantly vigorously stirred, obtains thermal decomposition product；3）It will
Step 2）The thermal decomposition product of acquisition is dialysed 20 ~ 30 hours in deionized water with 100-500D cellulose dialysis bag, Zhi Houyong
It is 4.0 ~ 6.0 that NaOH, which adjusts pH, carries out vacuum freeze drying to gained quantum point, nitrogen, sulphur codope are obtained with ultrapure water dissolution
Fluorescent carbon quantum dot aqueous solution.
2. nitrogen according to claim 1, sulphur codope fluorescent carbon quantum dot material preparation method, it is characterised in that institute
It states fluorescent carbon quantum dot aqueous solution and acquires fluorescent carbon quantum dot solid powder, fluorescent carbon quantum dot after rotating, being dried in vacuo
Average grain diameter is 3.82 nm.
3. nitrogen according to claim 1 or 2, sulphur codope fluorescent carbon quantum dot material preparation method, feature exists
In
By step 2）The thermal decomposition product of acquisition is dialysed 24 hours in deionized water with 100-500D cellulose dialysis bag, during which every
Replace extracellular fluid dialysis within 4 hours.
4. nitrogen according to claim 3, sulphur codope fluorescent carbon quantum dot material preparation method, it is characterised in that
PH is adjusted with 1M NaOH after dialysis, vacuum freeze drying is carried out to gained quantum point, dissolves quantum dot water with ultra-pure water
Solution.
5. the fluorescent carbon quantum dot of nitrogen made from any preparation methods of claim 1-4, sulphur codope, 4 DEG C are protected from light guarantor
It deposits spare.
6. the fluorescent carbon quantum dot of nitrogen according to claim 5, sulphur codope, it is characterised in that fluorescent carbon quantum dot material
Aqueous solution is in amber transparent shape, the absorption maximum of fluorescent carbon quantum dot solution after scanning the ultraviolet-visible absorption spectroscopy of the solution
Peak position is at 337nm.
7. the fluorescent carbon quantum dot of nitrogen according to claim 5 or 6, sulphur codope, it is characterised in that fluorescent carbon quantum dot
Average grain diameter is 3.82 nm.
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| CN109321237B (en) * | 2018-09-29 | 2021-11-23 | 中国林业科学研究院林产化学工业研究所 | Nitrogen-sulfur double-doped carbon dots and preparation method and application thereof |
| CN109207149A (en) * | 2018-11-02 | 2019-01-15 | 山西大学 | A kind of nitrogen, sulphur codope yellow fluorescence carbon dots and its application in anticancer drug |
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| CN110589799A (en) * | 2019-09-27 | 2019-12-20 | 浙江工业大学上虞研究院有限公司 | Preparation method and application of blue fluorescent carbon quantum dots |
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| CN111154485B (en) * | 2020-01-08 | 2022-08-19 | 沈阳药科大学 | Preparation of sulfur-nitrogen double-doped carbon quantum dot and application of sulfur-nitrogen double-doped carbon quantum dot in tetracycline detection |
| CN111718713A (en) * | 2020-07-21 | 2020-09-29 | 中南民族大学 | Carbon dot, preparation method and application thereof, and solid luminescent forming material |
| CN111718713B (en) * | 2020-07-21 | 2022-11-29 | 中南民族大学 | Carbon dot, preparation method and application thereof, and solid luminescent forming material |
| CN112250694A (en) * | 2020-11-17 | 2021-01-22 | 镇江红郡源医药科技有限公司 | Thiazolopyridinone compound and preparation method and application thereof |
| CN113045588A (en) * | 2021-03-22 | 2021-06-29 | 武汉理工大学 | Nitrogen-sulfur heterocyclic compound and preparation method and application thereof |
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