CN117986509A - Flower-shaped COF-based photocatalyst and preparation method and application thereof - Google Patents
Flower-shaped COF-based photocatalyst and preparation method and application thereof Download PDFInfo
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- CN117986509A CN117986509A CN202410125584.9A CN202410125584A CN117986509A CN 117986509 A CN117986509 A CN 117986509A CN 202410125584 A CN202410125584 A CN 202410125584A CN 117986509 A CN117986509 A CN 117986509A
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- 239000011941 photocatalyst Substances 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 36
- 230000001699 photocatalysis Effects 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 13
- 230000003647 oxidation Effects 0.000 claims abstract description 13
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims abstract description 11
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011968 lewis acid catalyst Substances 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 8
- 150000003568 thioethers Chemical class 0.000 claims abstract description 8
- QHQSCKLPDVSEBJ-UHFFFAOYSA-N 1,3,5-tri(4-aminophenyl)benzene Chemical compound C1=CC(N)=CC=C1C1=CC(C=2C=CC(N)=CC=2)=CC(C=2C=CC(N)=CC=2)=C1 QHQSCKLPDVSEBJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000001132 ultrasonic dispersion Methods 0.000 claims abstract description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000004005 microsphere Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- -1 2, 5-divinylbenzene dicarboxaldehyde Chemical compound 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 16
- 230000003197 catalytic effect Effects 0.000 abstract description 5
- 238000004108 freeze drying Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract 2
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 239000013310 covalent-organic framework Substances 0.000 description 41
- 239000008188 pellet Substances 0.000 description 13
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229940123973 Oxygen scavenger Drugs 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000003462 sulfoxides Chemical class 0.000 description 3
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000000026 X-ray photoelectron spectrum Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- YIYFFLYGSHJWFF-UHFFFAOYSA-N [Zn].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 Chemical group [Zn].N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 YIYFFLYGSHJWFF-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 238000013032 photocatalytic reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
- C08G12/08—Amines aromatic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/70—Oxidation reactions, e.g. epoxidation, (di)hydroxylation, dehydrogenation and analogues
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
Abstract
The invention discloses a flower-shaped COF-based photocatalyst and a preparation method and application thereof, and belongs to the technical field of photocatalytic material preparation. The invention provides a preparation method of a high-activity photocatalyst, which mainly aims at the problems of low efficiency and poor selectivity of the catalytic oxidation of sulfides by the conventional COF-based photocatalytic material. The method comprises the following steps: 1,3, 5-tri (4-aminophenyl) benzene (TPB) and 2, 5-Divinylbenzene (DVA) are dissolved in acetonitrile solution containing Lewis acid catalyst, after ultrasonic dispersion, the mixture is reacted for a period of time under the condition of room temperature, then washed by acetonitrile and ethanol, and finally the flower-shaped COF-based photocatalytic material is obtained after freeze drying. The preparation process of the photocatalytic material is simple, the reaction condition is mild, the unique structural morphology and the metal ion doping of the photocatalytic material effectively enhance the activity of the photocatalyst, and the high-efficiency and selective conversion of sulfides is promoted.
Description
Technical Field
The invention relates to a photocatalyst and a preparation method and application thereof, in particular to a flower-shaped COF-based photocatalyst and a preparation method and application thereof.
Background
Sulfoxide is used as an important chemical raw material and intermediate, and has wide application in pesticide and medicine industries. Typically, their production involves selective oxidation of sulfides. The key to efficient synthesis of sulfoxides is the choice of the appropriate oxidizing agent. Traditional oxidants, including electroreagents, ketone oxides and hydrogen peroxide, have the disadvantages of low selectivity, easy production of byproducts and environmental pollution. In recent years, a photocatalytic oxidation method has been attracting attention as an environmentally friendly sulfoxide synthesis method. The method adopts photocatalyst, such as titanium dioxide, metal organic frame, graphite phase carbon nitride, etc., and can realize clean and low energy consumption reaction. However, the photocatalytic efficiency of these catalysts is still limited and sometimes it is desirable to enhance their performance by means of auxiliary sacrificial agents.
Covalent Organic Frameworks (COFs) are a class of porous crystalline materials with well-defined framework structures and controlled porosity, and especially iminocofs have shown great advantage in heterogeneous catalysis and have also begun to be applied in recent years to catalytic oxidation of sulfides. In general, COFs combine with metal or inorganic salts to form heterogeneous catalysts, altering the band structure and facilitating the separation of photogenerated electrons. The introduction of functional units into COFs helps to achieve rapid electron transfer and improves product selectivity. For example, the use of imine COFs containing zinc porphyrin units can enhance the formation of singlet oxygen, which is beneficial for enhancing the selective oxidation of sulfides. However, COFs-based photocatalytic materials in current research have failed to achieve both high conversion and high selectivity of sulfides, which has limited their wide application in photocatalytic oxidation.
Disclosure of Invention
The invention aims to: the invention aims to provide a flower-shaped COF-based photocatalyst capable of simultaneously realizing high conversion rate and high selectivity of sulfide; the invention also aims at providing a preparation method of the flower-shaped COF-based photocatalyst; the invention also aims to provide an application of the flower-shaped COF-based photocatalyst in sulfide selective oxidation.
The technical scheme is as follows: the preparation method of the flower-shaped COF-based photocatalyst comprises the following steps: 1,3, 5-tri (4-aminophenyl) benzene and 2, 5-divinylbenzene are dissolved in a solvent containing Lewis acid catalyst, and after ultrasonic dispersion, the mixture reacts at room temperature to obtain the flower-shaped COF-based photocatalytic material.
Preferably, the molar ratio of the 1,3, 5-tri (4-aminophenyl) benzene, the 2, 5-divinylbenzene to the Lewis acid catalyst is 0.05-0.2:0.15-0.3:1-8, the reaction time is 24-72 hours at room temperature, the Lewis acid catalyst is a metal salt containing Zn 2+ or Cd 2+, and the Lewis acid is used as the catalyst, so that the polymerization reaction of the COF can be promoted, and the assembling and growing process of the framework structure can be regulated at a microscopic level, so that the forming of the flower-shaped COF balls is key.
Preferably, the solvent is acetonitrile, the ultrasonic dispersion time is 10-30 minutes, and the product obtained by the reaction is washed by acetonitrile and ethanol and then freeze-dried.
The morphology of the COF-based photocatalyst prepared by the preparation method is flower-shaped microspheres.
The flower-like COF-based photocatalyst can be applied to sulfide selective oxidation, and singlet oxygen dominates the efficient selective oxidation process of sulfide.
The beneficial effects are that: compared with the prior art, the invention has the following remarkable advantages:
(1) The flower-shaped COF ball has excellent light absorption capacity and charge transfer capacity, and singlet oxygen dominates the efficient selective oxidation process of sulfide, and the conversion rate and the selection are respectively up to 95% and 99%; after repeated recycling, the catalyst can still keep excellent catalytic performance and structural stability, and is suitable for the field of photocatalysis;
(2) The preparation process and the used equipment of the catalyst are simple, the reaction condition is mild, the catalyst can be produced in a large scale, and the catalyst has a good application prospect.
Drawings
FIG. 1 is a schematic diagram of the structural formula of the COF obtained in example 1;
FIG. 2 is an SEM image of the flower-shaped COF pellets obtained in example 1;
FIG. 3 is an XPS spectrum of the flower-like COF spheres obtained in example 1;
FIG. 4 is a performance chart of a three-cycle test of the flower-like COF pellets obtained in example 1;
FIG. 5 is a FTIR chart showing three catalytic experiments on the flower-shaped COF pellets obtained in example 1;
FIG. 6 is a comparison of the performance of the COF pellets obtained in example 1 in terms of sulfide conversion and selectivity in the presence of superoxide radicals and singlet oxygen scavenger.
Detailed Description
The technical scheme of the invention is further described below with reference to the accompanying drawings.
Example 1
1.2Mmol of zinc chloride is firstly dissolved in 8mL of acetonitrile solution, then 0.04mmol of 1,3, 5-tri (4-aminophenyl) benzene (TPB) and 0.06mmol of 2, 5-Divinylbenzene (DVA) are added into the acetonitrile solution, after ultrasonic dissolution for 20 minutes, the mixture is reacted for 72 hours at room temperature, and then the mixture is repeatedly washed by acetonitrile and ethanol, and the flower-shaped COF-based photocatalytic material is obtained after freeze drying.
Example 2
1.4Mmol of cadmium chloride is firstly dissolved in 10mL of acetonitrile solution, then 0.04mmol of 1,3, 5-tri (4-aminophenyl) benzene (TPB) and 0.06mmol of 2, 5-Divinylbenzene (DVA) are added into the acetonitrile solution, after ultrasonic dissolution for 20 minutes, the mixture is reacted for 72 hours at room temperature, and then the mixture is repeatedly washed by acetonitrile and ethanol, and the flower-shaped COF-based photocatalytic material is obtained after freeze drying.
Application examples
10Mg of the COF-based photocatalyst and 0.30mmol of methylphenyl sulfide were added to 5mL of a methanol solution, and subjected to ultrasonic treatment for 5 minutes. Then, oxygen was introduced into the mixture under stirring in a dark environment for 30 minutes. Subsequently, the reaction vessel was sealed and placed in a constant temperature water tank at 25℃and irradiated with light under a 300W xenon lamp equipped with a 420nm wavelength cut-off filter. After the reaction, the reaction solution was centrifuged, and 1mL of the supernatant solution was collected for gas phase-mass spectrometry. To evaluate the catalyst recycling, the collected COF-based photocatalyst was washed with ethanol and then dried under vacuum at 60 ℃ to perform the next round of photocatalytic test.
FIG. 1 is a schematic structural diagram of the COF obtained in example 1.
Fig. 2 is an SEM image of the petal-shaped COF pellets obtained in example 1, from which it can be seen that the synthesized COF pellets exhibited petal-shaped appearance.
Fig. 3 is an XPS spectrum of the flower-shaped COF ball obtained in example 1, and it is known from the figure that the COF contains five elements of C, N, O, zn and Cl, wherein C, N, O originate from the structural monomer itself, and Zn and Cl originate from the Lewis acid catalyst, which indicates that zinc chloride is doped into the framework structure of the COF during the polymerization reaction.
FIG. 4 is a graph showing the performance of the COF pellets obtained in example 1 in three cycles, wherein the photocatalytic performance of the COF pellets is stable, and the sulfide conversion and selectivity remain at 95% and 99% after three cycles, respectively.
Fig. 5 is a FTIR graph of the COF pellets obtained in example 1 after three catalytic experiments, from which it can be seen that the c=n characteristic absorption peak of the COF pellets did not disappear and decrease after three photocatalytic experiments, indicating that the material itself has good chemical and structural stability.
Fig. 6 is a comparison of the performance of the COF pellets of example 1 in terms of sulfide conversion and selectivity in the presence of superoxide radical and singlet oxygen scavenger, which shows that the COF pellets have significantly reduced sulfide conversion (compared to fig. 4) when singlet oxygen scavenger is present in the photocatalytic reaction system, while the superoxide radical scavenger has only a slight reduction in conversion and selectivity, indicating that singlet oxygen is the active species of COF pellets that dominate the photocatalytic oxidation of sulfide performance.
Claims (10)
1. The preparation method of the flower-shaped COF-based photocatalyst is characterized by comprising the following steps of: 1,3, 5-tri (4-aminophenyl) benzene and 2, 5-divinylbenzene are dissolved in a solvent containing Lewis acid catalyst, and after ultrasonic dispersion, the mixture reacts at room temperature to obtain the flower-shaped COF-based photocatalytic material.
2. The method for preparing a flower-like COF-based photocatalyst according to claim 1, wherein the molar ratio of 1,3, 5-tris (4-aminophenyl) benzene, 2, 5-divinylbenzene dicarboxaldehyde and Lewis acid catalyst is 0.05 to 0.2:0.15 to 0.3:1 to 8.
3. The method for preparing a flower-like COF-based photocatalyst according to claim 1, wherein the reaction time is 24 to 72 hours at room temperature.
4. The method for preparing a flower-like COF-based photocatalyst according to claim 1, wherein the Lewis acid catalyst is a metal salt containing Zn 2+ or Cd 2+.
5. The method for preparing a flower-like COF-based photocatalyst according to claim 1, wherein the solvent is acetonitrile.
6. The method for preparing a flower-like COF-based photocatalyst according to claim 1, wherein the ultrasonic dispersion time is 10 to 30 minutes.
7. The method for preparing a flower-like COF-based photocatalyst according to claim 1, wherein the reaction product is washed with acetonitrile and ethanol and then freeze-dried.
8. The flower-shaped COF-based photocatalyst prepared by the preparation method of any one of claims 1 to 7, which is characterized in that the appearance of the catalyst is flower-shaped microspheres.
9. Use of the COF-based photocatalyst in the form of a flower according to claim 8 in the selective oxidation of sulfides.
10. Use of a COF-based photocatalyst in the form of a flower according to claim 9, characterised in that singlet oxygen dominates the highly efficient selective oxidation process of sulfides.
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|---|---|---|---|
| CN202410125584.9A CN117986509B (en) | 2024-01-30 | 2024-01-30 | Flower-shaped COF-based photocatalyst and preparation method and application thereof |
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| CN202410125584.9A CN117986509B (en) | 2024-01-30 | 2024-01-30 | Flower-shaped COF-based photocatalyst and preparation method and application thereof |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170130349A1 (en) * | 2015-11-10 | 2017-05-11 | Indian Educational and Research Institute | Covalent organic frameworks as porous supports for non-noble metal based water splitting electrocatalysts |
| AU2020101584A4 (en) * | 2019-07-31 | 2020-09-10 | Hefei University Of Technology | Preparation method of metal monatomic composite loaded with covalent organic framework (COF)-derived carbon skeleton |
| CN111921559A (en) * | 2020-08-16 | 2020-11-13 | 复旦大学 | Single-site transition metal covalent organic framework photocatalyst and preparation method thereof |
| CN113751028A (en) * | 2021-10-12 | 2021-12-07 | 盐城工学院 | Organic-inorganic hybrid photocatalytic hydrogen evolution material and preparation method and application thereof |
-
2024
- 2024-01-30 CN CN202410125584.9A patent/CN117986509B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20170130349A1 (en) * | 2015-11-10 | 2017-05-11 | Indian Educational and Research Institute | Covalent organic frameworks as porous supports for non-noble metal based water splitting electrocatalysts |
| AU2020101584A4 (en) * | 2019-07-31 | 2020-09-10 | Hefei University Of Technology | Preparation method of metal monatomic composite loaded with covalent organic framework (COF)-derived carbon skeleton |
| CN111921559A (en) * | 2020-08-16 | 2020-11-13 | 复旦大学 | Single-site transition metal covalent organic framework photocatalyst and preparation method thereof |
| CN113751028A (en) * | 2021-10-12 | 2021-12-07 | 盐城工学院 | Organic-inorganic hybrid photocatalytic hydrogen evolution material and preparation method and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| BAI BIN 等: "Lewis Acid Catalyzed Synthesis of Vinylene Linked Two Dimensional Covalent Organic Frameworks", 《CHINESE JOURNAL OF CHEMISTRY》, vol. 40, no. 15, 29 April 2022 (2022-04-29), pages 1807 - 1812 * |
| YANG, YQ 等: "Synthesis of flower-like covalent organic frameworks for photocatalytic selective oxidation of sulfide", 《JOURNAL OF THE TAIWAN INSTITUTE OF CHEMICAL ENGINEERS》, vol. 164, 27 July 2024 (2024-07-27), pages 105680 * |
| 梅佩;张媛媛;冯霄;: "氨基酸功能化晶态多孔聚合物的研究进展", 化学学报, no. 10, 23 July 2020 (2020-07-23) * |
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