CN112574430A - Preparation method of supermolecule self-assembly PDI nano material based on solvent regulation - Google Patents
Preparation method of supermolecule self-assembly PDI nano material based on solvent regulation Download PDFInfo
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- 239000002904 solvent Substances 0.000 title claims abstract description 54
- 239000002086 nanomaterial Substances 0.000 title claims abstract description 23
- 238000001338 self-assembly Methods 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000002253 acid Substances 0.000 claims abstract description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims description 20
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 9
- 239000000725 suspension Substances 0.000 claims description 9
- 238000009210 therapy by ultrasound Methods 0.000 claims description 9
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 6
- 238000004108 freeze drying Methods 0.000 claims description 5
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- 239000003344 environmental pollutant Substances 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 6
- 238000013033 photocatalytic degradation reaction Methods 0.000 abstract description 6
- 231100000719 pollutant Toxicity 0.000 abstract description 6
- 239000000178 monomer Substances 0.000 abstract description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 abstract 1
- AIPBSZJAQGGCPD-UHFFFAOYSA-N molport-035-677-503 Chemical compound C=12C3=CC=C(C(N(C(CC)CC)C4=O)=O)C2=C4C=CC=1C1=CC=C2C(=O)N(C(CC)CC)C(=O)C4=CC=C3C1=C42 AIPBSZJAQGGCPD-UHFFFAOYSA-N 0.000 abstract 1
- 230000001699 photocatalysis Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000007146 photocatalysis Methods 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002121 nanofiber Substances 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- WSRHMJYUEZHUCM-UHFFFAOYSA-N perylene-1,2,3,4-tetracarboxylic acid Chemical compound C=12C3=CC=CC2=CC=CC=1C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C2=C1C3=CC=C2C(=O)O WSRHMJYUEZHUCM-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 230000029553 photosynthesis Effects 0.000 description 1
- 238000010672 photosynthesis Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
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- 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
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- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/39—Photocatalytic properties
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- C02F1/30—Treatment of water, waste water, or sewage by irradiation
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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- C02F2101/30—Organic compounds
- C02F2101/38—Organic compounds containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
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Abstract
The invention relates to a preparation method of a supermolecule self-assembly PDI nano material based on solvent regulation, belonging to the technical field of material science and engineering. According to the invention, different solvents are used to regulate and control the morphology of the material so as to influence the performance of the material in photocatalytic degradation of environmental water phenol pollutants. The solvent mainly comprises water, acetone, isopropanol, methanol, ethanol and chloroform. After N, N' -bis (3-pentyl) perylene-3, 4,9, 10-bis (dicarboximide) (PDI) is dissolved in one of the solvents, different acids are dripped to enable self-assembly of monomers PDI to form a super molecular system. The invention has the advantages of high efficiency, simplicity, economy and the like.
Description
Technical Field
The invention relates to a preparation method of a supermolecule self-assembly PDI nano material based on solvent regulation, belonging to the technical field of material science and engineering.
Background
In recent years, organic catalysts have received much attention from researchers. Organic materials have many advantages over inorganic materials, such as tunable electronic and optical properties, structural flexibility, low cost, and abundant storage. Recently, self-assembled supramolecular organic materials have shown great potential in the field of photocatalysis, such as Diketopyrrolopyrroles (DPP), porphyrins (TPP), Perylene Monoimides (PMI) and Perylenetetracarboxylic Diimides (PDI). In particular, PDI and its derivatives, which are a typical n-type organic semiconductor, are used for photocatalysis due to their high photo-thermal stability, excellent charge mobility and electron affinity.
Recently, self-assembled supramolecules PDI have been investigated for various applications, such as photocatalytic water splitting, photocatalytic degradation, organic photosynthesis, etc. However, the application of PDI in photocatalysis is greatly limited due to the disadvantages of poor stability of the photogenerated carrier in the photocatalysis process, easy recombination, poor adsorption capacity and the like. By constructing the supermolecule PDI nano material with special morphology, the separation efficiency and the adsorption capacity of the photoproduction electron-hole pair can be effectively improved. According to the invention, through a rapid and simple solution dispersion method, a monomer PDI is self-assembled into a supermolecule nanofiber through hydrogen bonds and pi-pi stacking. By using different solvents, the supramolecule PDI with morphological evolution can be obtained, the capability of the supramolecule PDI in photocatalytic degradation of pollutants is further researched, and the influence of morphology on performance is explored.
Disclosure of Invention
The invention relates to a preparation method of a supermolecule self-assembly PDI nano material, which utilizes different solvents to regulate and control the appearance of the material, thereby influencing the performance of the material in photocatalytic degradation of pollutants.
The invention provides a preparation method of a self-assembled supermolecule PDI nano material, which comprises the following steps:
(1) measuring a solvent by a measuring cylinder, adding the solvent into a beaker, transferring triethanolamine by a liquid transfer gun, weighing PDI by a balance, adding the PDI into the beaker while stirring, and sequentially carrying out ultrasonic treatment and stirring treatment to obtain a mixed solution.
The solvent is one of water, acetone, isopropanol, methanol, ethanol and chloroform; through comparative experiments, the solvent is preferably acetone;
the amount of the solvent and the dropping amount of the triethanolamine are changed according to the amount of the added PDI and the solubility of the solvent, and the proportion of the solvent, the triethanolamine and the PDI is controlled to be 100-200 mL: 400-600 μ L: 0.02-0.2 g. Through a large number of experimental optimizations, the proportion of solvent, triethanolamine and PDI of the best photocatalytic performance sample is 130 mL: 400 μ L: 0.03 g.
The ultrasonic frequency is 40K Hz, the ultrasonic treatment time is 15min, and the stirring treatment time is 1 h.
(2) And (3) measuring acid by using a measuring cylinder, slowly dropwise adding the acid into the mixed solution obtained in the step (1), and stirring to obtain a suspension.
The acid is HCl or HNO3And H2SO4The concentration of the acid is 1-4mol/L, the dropping amount is changed according to the precipitation of the dark red solid PDI, and the ratio of the acid to the solvent in the step (1) is 30-150: 100-; the stirring treatment time is 4 h.
(3) Standing the suspension obtained in the step (2), and centrifuging by a centrifuge to obtain dark red solid.
The standing time is 30 min.
(4) And (4) washing the dark red solid obtained in the step (3) with deionized water, and then performing freeze drying to obtain the supramolecular self-assembly PDI nano material based on solvent regulation.
The freeze drying time is 24-48h, and the pressure is 10-40 Pa.
Compared with other reported technologies, the method adopted by the invention can ensure that the dried sample keeps the original physical properties, so that the appearance of the sample is not damaged. Through the selection of a solvent, supermolecule self-assembled PDI nano-materials with different morphologies are obtained, and the performance of photocatalytic degradation of pollutants of the supermolecule self-assembled PDI nano-materials is further influenced.
Drawings
FIG. 1 is a scanning electron microscope of PDI nano-materials prepared by the method of the present invention under different solvents (wherein, the solvent in the diagram a is water, the solvent in the diagram b is ethanol, the solvent in the diagram c is methanol, and the solvent in the diagram d is acetone). As can be seen from the figure, when the solvent is water, the sample presents a blocky shape, when the solvent is ethanol and methanol, the sample is more regular in shape, and when the solvent is acetone, the self-assembled PDI supermolecular system presents a nano-fiber shape, the width is 1-10 μm, and the length is 30-80 μm.
FIG. 2 is a test chart of the performance of the PDI nano material in photocatalytic degradation RhB in different solvents prepared by the method. As can be seen from the figure, when the solvent is water, the degradation capability of the sample is weak, only 41% of RhB pollutants can be degraded after 4 hours of degradation, when the solvent is acetone, the degradation capability can be effectively improved, and 85% of RhB pollutants can be degraded in the same time.
Detailed Description
The invention provides a preparation method of a self-assembled supermolecule PDI nano material, which comprises the following steps:
(1) measuring a solvent by a measuring cylinder, adding the solvent into a beaker, transferring triethanolamine by a liquid transfer gun, weighing PDI by a balance, adding the PDI into the beaker while stirring, and sequentially carrying out ultrasonic treatment and stirring treatment to obtain a mixed solution.
The solvent is one of water, acetone, isopropanol, methanol, ethanol and chloroform, and through a comparative experiment, the solvent is preferably acetone;
the amount of the solvent and the dropping amount of the triethanolamine are changed according to the amount of the added PDI and the solubility of the solvent, in a specific embodiment, for example, the usage amount of the solvent is 100-200mL, the usage amount of the triethanolamine is 400-600 μ L, the usage amount of the PDI is 0.02-0.2g, through optimization of a large number of experiments, the usage amount of the solvent of the sample with the optimal photocatalytic performance is 130mL, the usage amount of the triethanolamine is 400 μ L, and the usage amount of the PDI is 0.03 g;
the ultrasonic frequency is 40K Hz, the ultrasonic treatment time is 15min, and the stirring treatment time is 1 h.
(2) Measuring acid by using a measuring cylinder, slowly dropwise adding the acid into the mixed solution obtained in the step (1), and stirring for 4 hours to obtain a suspension. The acid is HCl or HNO3And H2SO4Wherein the concentration of the acid is 1-4mol/L,the dropping amount varies according to the precipitation of the dark red solid PDI, and is 30-150 mL.
(3) Standing the suspension obtained in the step (2) for 30min, and centrifuging by a centrifuge to obtain dark red solid.
(4) And (3) washing the dark red solid obtained in the step (3) by using deionized water, and then performing freeze drying treatment for 24-48h under the high vacuum (10-40 Pa).
The following describes embodiments of the method of the invention:
example 1:
firstly, a measuring cylinder measures 100mL of deionized water and adds the deionized water into a beaker, a liquid transfer gun transfers 400 μ L of triethanolamine and adds the triethanolamine and the PDI into the beaker, a balance weighs 0.175g of the PDI, the PDI is added into the beaker while stirring, ultrasonic treatment is carried out for 15 minutes, the ultrasonic frequency is 40K Hz, and stirring treatment is carried out for 1 hour. The measuring cylinder measures 35mL of 4mol/L HCl and slowly drops into the solution, and the solution is stirred for 4 hours. Insoluble red solids immediately appeared and these suspensions were allowed to stand for an additional 0.5h, then the resulting dark red solids were collected by centrifuge and washed several times with deionized water. Flash freezing with liquid nitrogen followed by drying for 24h with a freeze dryer at a pressure of 20Pa high vacuum. The obtained sample is the self-assembled supermolecule PDI nano material.
Example 2:
firstly, measuring 110mL of absolute ethyl alcohol by using a measuring cylinder, adding the absolute ethyl alcohol into a beaker, transferring 500 mu L of triethanolamine by using a liquid transfer gun, adding the triethanolamine into the beaker by using a balance to weigh 0.1g of PDI, stirring and adding the PDI into the beaker, and carrying out ultrasonic treatment for 15min at the ultrasonic frequency of 40K Hz for 1 h. Measuring 65mL of 4mol/L HNO by using measuring cylinder3Slowly dropping the mixture into the solution, and stirring for 4 hours. Insoluble red solids immediately appeared and these suspensions were allowed to stand for an additional 0.5h, then the resulting dark red solids were collected by centrifuge and washed several times with deionized water. Flash freezing was performed using liquid nitrogen followed by drying for 48h using a freeze dryer at a pressure of 20Pa of high vacuum. The obtained sample is the self-assembled supermolecule PDI nano material.
Example 3:
first, a measuring cylinder measures 130mL of acetone into a beaker,and (3) transferring 400 mu L of triethanolamine by a liquid transfer gun into a beaker, weighing 0.03g of PDI by a balance, adding the PDI into the beaker while stirring, and carrying out ultrasonic treatment for 15min at the ultrasonic frequency of 40K Hz for 1 h. Measuring cylinder measuring 100mL 2mol/L H2SO4Slowly dropping the mixture into the solution, and stirring for 4 hours. Insoluble red solids immediately appeared and these suspensions were allowed to stand for an additional 0.5h, then the resulting dark red solids were collected by centrifuge and washed several times with deionized water. Flash freezing was performed using liquid nitrogen followed by drying for 48h using a freeze dryer at a pressure of 20Pa of high vacuum. The obtained sample is the self-assembled supermolecule PDI nano material.
Claims (6)
1. The preparation method of the supermolecule self-assembly PDI nano material based on solvent regulation is characterized by comprising the following specific steps:
(1) measuring a solvent by a measuring cylinder, adding the solvent into a beaker, transferring triethanolamine by a liquid transfer gun, adding PDI weighed by a balance into the beaker while stirring, and sequentially performing ultrasonic treatment and stirring treatment to obtain a mixed solution;
(2) measuring acid by using a measuring cylinder, slowly dropwise adding the acid into the mixed solution obtained in the step (1), and stirring to obtain a suspension;
(3) standing the suspension obtained in the step (2), and centrifuging by a centrifugal machine to obtain a dark red solid;
(4) and (4) washing the dark red solid obtained in the step (3) with deionized water, and then performing freeze drying to obtain the supramolecular self-assembly PDI nano material based on solvent regulation.
2. The method for preparing the supramolecular self-assembly PDI nanomaterial based on solvent regulation as claimed in claim 1, wherein in the step (1), the solvent is one of water, acetone, isopropanol, methanol, ethanol and chloroform; the amount of the solvent and the dropping amount of the triethanolamine are changed according to the amount of the added PDI and the solubility of the solvent, and the proportion of the solvent, the triethanolamine and the PDI is controlled to be 100-200 mL: 400-600 μ L: 0.02-0.2 g; the ultrasonic frequency is 40K Hz, the ultrasonic treatment time is 15min, and the stirring treatment time is 1 h.
3. The method for preparing supramolecular self-assembly PDI nanomaterial based on solvent regulation as claimed in claim 2, wherein in step (1), the solvent is acetone; the ratio of triethanolamine to PDI was 130 mL: 400 μ L: 0.03 g.
4. The method for preparing supramolecular self-assembly PDI nanomaterial based on solvent regulation as claimed in claim 1, wherein in step (2), the acid is HCl, HNO3And H2SO4The concentration of the acid is 1-4mol/L, the dropping amount is changed according to the precipitation of the dark red solid PDI, and the ratio of the acid to the solvent in the step (1) is 30-150: 100-; the stirring treatment time is 4 h.
5. The method for preparing supramolecular self-assembly PDI nanomaterial based on solvent regulation as claimed in claim 1, wherein in step (3), the standing time is 30 min.
6. The method for preparing supramolecular self-assembly PDI nanomaterial based on solvent regulation as claimed in claim 1, wherein in step (4), the freeze-drying treatment time is 24-48h, and the pressure is high vacuum 10-40 Pa.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114011450A (en) * | 2021-11-08 | 2022-02-08 | 威腾电气集团股份有限公司 | g-C3N4Preparation method and application of organic photocatalyst loaded with PDI (Poly-propylene-diene monomer) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103980398A (en) * | 2014-05-05 | 2014-08-13 | 北京化工大学 | Self-assembly with perylene derivative or analog as fluorescent chromogenic end group and preparation method thereof |
| CN104028308A (en) * | 2014-06-20 | 2014-09-10 | 中国科学院新疆理化技术研究所 | Nanometer photo-catalyst used in producing hydrogen by decomposing water under visible light response and application of nanometer photo-catalyst |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103980398A (en) * | 2014-05-05 | 2014-08-13 | 北京化工大学 | Self-assembly with perylene derivative or analog as fluorescent chromogenic end group and preparation method thereof |
| CN104028308A (en) * | 2014-06-20 | 2014-09-10 | 中国科学院新疆理化技术研究所 | Nanometer photo-catalyst used in producing hydrogen by decomposing water under visible light response and application of nanometer photo-catalyst |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114011450A (en) * | 2021-11-08 | 2022-02-08 | 威腾电气集团股份有限公司 | g-C3N4Preparation method and application of organic photocatalyst loaded with PDI (Poly-propylene-diene monomer) |
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