CN113861435B - Method for rapidly preparing hydrogen bond organic framework material based on electric field and application - Google Patents
Method for rapidly preparing hydrogen bond organic framework material based on electric field and application Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 65
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 59
- 239000001257 hydrogen Substances 0.000 title claims abstract description 59
- 239000013384 organic framework Substances 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 26
- 230000005684 electric field Effects 0.000 title claims abstract description 22
- 239000013110 organic ligand Substances 0.000 claims abstract description 25
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- 239000003053 toxin Substances 0.000 claims abstract description 13
- 231100000765 toxin Toxicity 0.000 claims abstract description 13
- 108700012359 toxins Proteins 0.000 claims abstract description 13
- 238000001631 haemodialysis Methods 0.000 claims abstract description 9
- 230000000322 hemodialysis Effects 0.000 claims abstract description 9
- 238000005406 washing Methods 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 238000005303 weighing Methods 0.000 claims abstract description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 238000005119 centrifugation Methods 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- -1 (6-carboxynaphthalene) pyrene Chemical compound 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000001737 promoting effect Effects 0.000 abstract 1
- 239000002994 raw material Substances 0.000 abstract 1
- 238000001179 sorption measurement Methods 0.000 description 21
- 102000016943 Muramidase Human genes 0.000 description 10
- 108010014251 Muramidase Proteins 0.000 description 10
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 239000004202 carbamide Substances 0.000 description 10
- 239000004325 lysozyme Substances 0.000 description 10
- 229960000274 lysozyme Drugs 0.000 description 10
- 235000010335 lysozyme Nutrition 0.000 description 10
- 238000000502 dialysis Methods 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000003463 adsorbent Substances 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 208000020832 chronic kidney disease Diseases 0.000 description 2
- 208000028208 end stage renal disease Diseases 0.000 description 2
- 201000000523 end stage renal failure Diseases 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 238000001000 micrograph Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000002054 transplantation Methods 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 238000001132 ultrasonic dispersion Methods 0.000 description 2
- 208000009304 Acute Kidney Injury Diseases 0.000 description 1
- 208000033626 Renal failure acute Diseases 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- 201000011040 acute kidney failure Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013310 covalent-organic framework Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000012621 metal-organic framework Substances 0.000 description 1
- ABMDIECEEGFXNC-UHFFFAOYSA-N n-ethylpropanamide Chemical compound CCNC(=O)CC ABMDIECEEGFXNC-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000013354 porous framework Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000012959 renal replacement therapy Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
Abstract
The invention discloses a method for rapidly preparing a hydrogen bond organic framework material based on an electric field and application thereof. The method comprises the following steps: (1) weighing the raw materials; (2) Dissolving an organic ligand in an organic solvent, and adding another organic solvent after the organic ligand is completely dissolved; (3) And (3) introducing direct current with a certain voltage into the solution mixed with the organic ligand, centrifuging and washing the product for multiple times, and drying to obtain the hydrogen bond organic framework material. The invention shortens the time for preparing the hydrogen bond organic frame by promoting the formation of the hydrogen bond under the action of an externally applied electric field, and realizes the rapid and efficient removal of the small and medium molecular toxins in the hemodialysis process by means of the large specific surface area and the porous structure of the hydrogen bond organic frame, good biocompatibility and repeated use performance.
Description
Technical field:
the invention relates to a method for rapidly preparing a hydrogen bond organic framework material based on an electric field and application thereof, belonging to the field of hydrogen bond organic frameworks.
The background technology is as follows:
currently, over 300 tens of thousands of people worldwide are affected by end-stage renal disease, dialysis or kidney transplantation being the only option for these patients to avoid death, but only a few fortunate people are able to conduct kidney transplantation, most of them relying on dialysis. Most of chronic dialysis patients are disabled, cannot perform normal activities of daily living, and have poor quality of life and high mortality. To reduce the impact of end stage renal disease on these patients, frequent and prolonged dialysis treatments are required. In addition, the pandemic of new coronaries has become a significant worldwide crisis. Although respiratory symptoms are a key feature of this disease, many patients with new coronaries also suffer from acute kidney injury, which exacerbates the mortality of the patient and has to be treated by renal replacement therapy. However, during the course of treatment, the supply of dialysate becomes strained and under-supplied.
The dialysis machine used clinically at present has serious limitation to use because of the defects of large occupied area, more waste liquid and low toxin removal efficiency. Therefore, there is an urgent need to develop a new miniaturized dialysis machine that can perform rapid and efficient dialysis on dialysis patients, and the key of this is the development of efficient adsorbents. In addition, there is also an urgent need to develop a material capable of efficiently and rapidly removing toxins in the dialysate and restoring electrolyte concentration for repeated use of the dialysate. Therefore, it is becoming more and more important to develop an adsorbent having a rapid, efficient adsorption of toxic substances in a dialysis process. This is also one of the development directions for future development of small hemodialysis machines and reuse of dialysate.
Hydrogen bonded organic framework materials (HOFs) are a class of crystalline porous framework materials formed by the hydrogen bonding of organic building blocks. In addition to hydrogen bonding, pi-pi interactions, electrostatic interactions, and other intermolecular forces such as van der Waals forces are also important for the construction and stability of HOFs. Similar to MOFs/COFs, HOFs also have the characteristics of large specific surface area, multiple structures, adjustable pore channel shape and size, modifiable pore surface and the like. However, HOFs materials have some own unique advantages because they are constructed by hydrogen bonds, and the hydrogen bond forces are generally weaker and more reversible than the strength of coordinate or covalent bonds: (1) the preparation conditions of HOFs are milder; (2) HOFs have good solution processability; (3) The HOFs material has better self-healing capacity and regeneration capacity; (4) Since most HOFs materials do not contain metal ions, the metal-free property gives the HOFs materials better biocompatibility and lower cytotoxicity, so that the HOFs have great application potential in biological application. The growth time of the HOFs material is long at present, the growth time of the HOFs material can be obviously shortened under the action of an electric field, the crystal form of the HOFs material is not changed, and a new thought is provided for shortening the growth time of the HOFs material.
The invention comprises the following steps:
the invention aims to rapidly prepare a hydrogen bond organic framework material by using an externally applied electric field method, and the hydrogen bond organic framework material is used for rapidly and efficiently removing medium and small molecular toxins in a hemodialysis process. In order to achieve the above purpose, the invention provides a method for rapidly preparing a hydrogen bond organic framework material based on an electric field and application thereof. The method is characterized by comprising the following specific steps of:
(1) Weighing an organic ligand and an organic solvent;
(2) Dissolving an organic ligand in an organic solvent, adding another organic solvent after the organic ligand is completely dissolved, and uniformly stirring;
(3) And (3) introducing direct current with a certain voltage into the solution mixed with the organic ligand, and after a certain time of reaction, centrifuging, washing and drying the product for a plurality of times to obtain the product.
Further, the organic ligand in the step (1) is 1,3,6, 8-tetra (6-carboxynaphthalene) pyrene, and the organic solvent is one or more of dimethyl sulfoxide, N ' -dimethylformamide, N ' -dimethylacetamide and N, N ' -diethylformamide.
Further, the adding amount of the organic ligand in the step (2) is 10-400 mg, and the mass-volume ratio of the organic ligand to the organic solvent is 1:2-2:1 (mg: mL).
Further, the dissolution in the step (2) can be rapidly and uniformly dispersed by an ultrasonic or stirring method.
Further, the organic solvent in the step (2) is one or more of tetrahydrofuran, acetone and methanol.
Further, the voltage applied in the step (3) is 0-90V, and the reaction time is 0-6 h.
Further, the rotational speed of centrifugation in the step (3) is 8000-12000 r/min, the centrifugation time is 10-30 min, the washing times are 2-7 times, and the drying temperature is 40-80 ℃.
Further, the solvent used for washing in the step (3) is one or more of ethanol, water and acetone.
The invention also provides application of the hydrogen bond organic framework material in hemodialysis. Preferably, it is used as an adsorbent for removing toxins in hemodialysis.
Preferably, the toxins include medium molecular toxins and small molecular toxins.
Preferably, the medium molecular toxins are represented by lysozyme and the small molecular toxins are represented by urea.
As described above, the method and application of the present invention for rapidly preparing hydrogen bonding organic framework material based on electric field have the following beneficial effects:
(1) The invention accelerates the deprotonation of carboxyl on the ligand under the promotion of an electric field, utilizes the synergistic effect of multiple hydrogen bonds between carboxyl on the ligand and pi-pi interaction force between pyrene, and obtains the hydrogen bond organic framework material constructed based on 1,3,6, 8-tetra (6-carboxynaphthalene) pyrene ligand in a short time.
(2) The hydrogen bond organic framework material has good biocompatibility and lower biotoxicity, and is applied to the hemodialysis process, thereby being beneficial to improving the removal of the small and medium molecular toxins. The adsorption quantity of the hydrogen bond organic framework material to urea is about 40mg/g, and the clearance rate is about 60%. The adsorption capacity of the hydrogen bond organic framework material to lysozyme is about 30mg/g, and the clearance rate reaches 80%. The hydrogen bond organic framework material has the advantages of small dosage, short clearing time, high clearing efficiency and the like, and has wide application prospect in the aspect of clearing hemodialysis toxin.
Description of the drawings:
FIG. 1 (a) is a chemical structural formula of an organic ligand according to example 1 of the present invention, and (b) is a schematic structural diagram of a hydrogen-bonded organic framework material according to example 1 of the present invention;
FIG. 2 is a simulated XRD spectrum and a powder XRD spectrum of a hydrogen bonding organic framework material according to example 1 of the present invention;
FIG. 3 is a scanning electron microscope image of a hydrogen bonding organic framework material according to example 1 of the present invention;
FIG. 4 shows the results of the adsorption experiment of the hydrogen bond organic frame material on urea in example 1 of the present invention, (a) the adsorption amount of the hydrogen bond organic frame material with the same content on urea at different adsorption times, and (b) the removal efficiency of the hydrogen bond organic frame material with different contents on urea;
FIG. 5 shows the results of an adsorption experiment of the organic frame material with hydrogen bond on lysozyme in example 1 of the present invention, (a) the adsorption amount of the organic frame material with hydrogen bond on lysozyme at different adsorption times with the same content, (b) the removal efficiency of the organic frame material with hydrogen bond on lysozyme with different content;
specific embodiments:
embodiments of the present invention will now be described with reference to specific examples, which are intended to be illustrative of the invention and are not intended to limit the scope of the invention. Unless otherwise indicated, all technical means used in the present invention are methods well known to those skilled in the art.
Example 1:
(1) 50mg of 1,3,6, 8-tetrakis (6-carboxynaphthalene) pyrene was weighed and added to a beaker, 15mL of N, N' -dimethylformamide was measured and added to a beaker containing the organic ligand, and the dispersion was performed by ultrasonic until the organic ligand was completely dissolved.
(2) 80mL of acetone in an amount of about 80mL was added to the beaker with stirring at 300 rpm. The rotation speed was adjusted to 50 rpm, and a DC power supply was used to supply 25V DC power to the beaker for 4 hours.
(3) The product was isolated by centrifugation at 8000 rpm for 7 minutes and washed with 30mL of acetone and centrifuged again for three times. The hydrogen bond organic framework material obtained was dried under vacuum at 60 ℃ with a yield of 82.8%.
Example 2:
(1) 200mg of 1,3,6, 8-tetrakis (6-carboxynaphthalene) pyrene was weighed out and added to a beaker, and 50mL of N, N' -dimethylformamide was weighed out and added to the beaker containing the organic ligand, and the mixture was subjected to ultrasonic dispersion until the organic ligand was completely dissolved.
(2) A measured amount of 240mL of acetone was added to the beaker under stirring at 400 rpm. The rotation speed was adjusted to 50 rpm, and 70V of dc was supplied to the beaker using a dc power supply for 2 hours.
(3) The product was isolated by centrifugation at 8000 rpm for 7 minutes and washed with 50mL of acetone and centrifuged again for three times. The hydrogen bond organic framework material obtained was dried under vacuum at 60 ℃ with a yield of 85.4%.
Example 3:
(1) 100mg of 1,3,6, 8-tetrakis (6-carboxynaphthalene) pyrene was weighed and added to a beaker, and 20mL of dimethyl sulfoxide was weighed into the beaker containing the organic ligand, and the mixture was subjected to ultrasonic dispersion until the organic ligand was completely dissolved.
(2) A measured amount of 60mL of tetrahydrofuran was added to the beaker under stirring at 400 rpm. The rotation speed was adjusted to 50 rpm, and a 50V DC was supplied to the beaker using a DC power supply for 3 hours.
(3) The product was isolated by centrifugation at 8000 rpm for 7 minutes and washed with 40mL acetone and centrifuged again for three times. The resulting hydrogen bonded organic framework material was vacuum dried at 60 ℃ with a yield of 79.5%.
Performance testing
Fig. 1 is a schematic structural diagram of a hydrogen-bonded organic framework material prepared by applying an electric field in example 1, (a) is a chemical structural formula of an organic ligand, and (b) is a schematic structural diagram of a hydrogen-bonded organic framework material. As can be seen from FIG. 1, the hydrogen bond organic framework material has a two-dimensional pore size of
Fig. 2 is a simulated XRD spectrum and a powder XRD spectrum of the hydrogen bonded organic framework material prepared by an applied electric field in example 1. As can be seen from fig. 2, the hydrogen-bonded organic framework material prepared by using the applied electric field of the present invention has a good purity, and can maintain crystallinity well.
FIG. 3 is a scanning electron microscope image of a hydrogen bonded organic framework material prepared by an applied electric field in example 1. As can be seen from fig. 3, the hydrogen-bonded organic framework material has a rod shape.
Fig. 4 shows the adsorption experimental results of the hydrogen bond organic frame material prepared by the applied electric field in example 1 on urea, (a) the adsorption amount of the hydrogen bond organic frame material on urea at different adsorption times, and (b) the removal efficiency of the hydrogen bond organic frame material with different contents on urea. From FIG. 4, it is clear that when the adsorption time is 30 minutes, the adsorption amount of the hydrogen bond organic frame material to urea reaches the maximum value, about 40mg/g, which indicates that the hydrogen bond organic frame material has a rapid adsorption performance to urea and the removal rate is about 60%.
Fig. 5 shows the results of the adsorption experiment of the lysozyme by the hydrogen bond organic frame material prepared by the external electric field in example 1, (a) the adsorption amount of the lysozyme by the hydrogen bond organic frame material at different adsorption times, and (b) the removal efficiency of the lysozyme by the hydrogen bond organic frame material with different addition amounts. As can be seen from FIG. 5, when the adsorption time is only 10min, the adsorption amount of the hydrogen bond organic frame material to lysozyme is already the maximum, about 30mg/g, which indicates that the hydrogen bond organic frame material also has a rapid adsorption function to lysozyme and the removal rate can reach 80%.
Claims (6)
1. The method for rapidly preparing the hydrogen bond organic framework material based on the electric field is characterized by comprising the following steps of:
(1) Weighing an organic ligand and an organic solvent;
(2) Dissolving an organic ligand in an organic solvent, adding another organic solvent after the organic ligand is completely dissolved, and uniformly stirring;
(3) Introducing direct current with a certain voltage into the solution mixed with the organic ligand, centrifuging and washing the product for a plurality of times after reacting for a certain time, and drying to obtain the product; the organic ligand in the step (1) is 1,3,6, 8-tetra (6-carboxynaphthalene) pyrene, and the organic solvent is one or more of dimethyl sulfoxide, N ' -dimethylformamide, N ' -dimethylacetamide, N ' -diethylformamide, tetrahydrofuran, acetone and methanol; the mass-volume ratio of the organic ligand to the organic solvent in the step (2) is 1:2-2:1 (mg: mL); and (3) applying voltage of 0-90V and reacting for 0-6 h.
2. The method for rapidly preparing hydrogen bonding organic framework materials based on an electric field according to claim 1, wherein the method comprises the following steps: the addition amount of the organic ligand in the step (2) is 10-400 mg.
3. The method for rapidly preparing hydrogen bonding organic framework materials based on an electric field according to claim 1, wherein the method comprises the following steps: the dissolution in the step (2) can be rapidly and uniformly dispersed by an ultrasonic or stirring method.
4. The method for rapidly preparing hydrogen bonding organic framework materials based on an electric field according to claim 1, wherein the method comprises the following steps: the rotational speed of centrifugation in the step (3) is 8000-12000 r/min, the centrifugation time is 10-30 min, the washing times are 2-7 times, and the drying temperature is 40-80 ℃.
5. The application of the hydrogen bond organic framework material obtained by the method for rapidly preparing the hydrogen bond organic framework material based on the electric field according to any one of claims 1 to 4, which is characterized in that: the hydrogen bond organic framework material can be used for rapidly and efficiently removing the middle and small molecular toxins in the hemodialysis process.
6. The application of the hydrogen bond organic framework material obtained by the method for rapidly preparing the hydrogen bond organic framework material based on the electric field as claimed in claim 5, which is characterized in that: before hemodialysis, the hydrogen bond organic frame material is activated for 5-20 h under the vacuum condition of 80-120 ℃.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020252536A1 (en) * | 2019-06-19 | 2020-12-24 | The University Of Adelaide | Hydrogen-bonded organic framework systems |
| CN112812316A (en) * | 2020-12-23 | 2021-05-18 | 华南理工大学 | Method for preparing ZIF-8 material under external electric field condition |
| CN112920794A (en) * | 2021-02-05 | 2021-06-08 | 浙江师范大学 | Hydrogen bond organic framework composite luminescent material and preparation method thereof |
| CN113150305A (en) * | 2021-04-30 | 2021-07-23 | 北京化工大学 | Porous hydrogen bond organic framework material and preparation method thereof |
| WO2021170775A1 (en) * | 2020-02-27 | 2021-09-02 | Technische Universität Berlin | Semiconductive and proton-conductive porous hydrogen-bonded frameworks |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020252536A1 (en) * | 2019-06-19 | 2020-12-24 | The University Of Adelaide | Hydrogen-bonded organic framework systems |
| WO2021170775A1 (en) * | 2020-02-27 | 2021-09-02 | Technische Universität Berlin | Semiconductive and proton-conductive porous hydrogen-bonded frameworks |
| CN112812316A (en) * | 2020-12-23 | 2021-05-18 | 华南理工大学 | Method for preparing ZIF-8 material under external electric field condition |
| CN112920794A (en) * | 2021-02-05 | 2021-06-08 | 浙江师范大学 | Hydrogen bond organic framework composite luminescent material and preparation method thereof |
| CN113150305A (en) * | 2021-04-30 | 2021-07-23 | 北京化工大学 | Porous hydrogen bond organic framework material and preparation method thereof |
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