CN113861435A - 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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- -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
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 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 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 promotes the formation of hydrogen bonds through the action of an external electric field to shorten the time for preparing the hydrogen bond organic framework, and realizes the quick and efficient removal of 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 framework, and the good biocompatibility and reusability.
Description
The technical field is as follows:
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.
Background art:
currently over 300 million 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 lucky people are able to perform kidney transplantation, the vast majority of them rely on dialysis. Most chronic dialysis patients are disabled, cannot carry out normal daily activities, have poor quality of life and high mortality. To reduce the effects of end stage renal disease in these patients, frequent and prolonged dialysis treatment is required. In addition, the pandemic of new coronary pneumonia has become a significant worldwide crisis. Although respiratory symptoms are a key feature of the disease, many patients with new coronary pneumonia also suffer from acute kidney damage, which exacerbates patient mortality and has to be treated by renal replacement therapy. However, during the treatment, the supply of dialysate becomes strained, and the supply is short.
The dialysis machine used clinically at present has seriously limited its use because of the disadvantages of large floor space, more waste liquid generation and low toxin removing efficiency. Therefore, there is an urgent need to develop a new and miniaturized dialysis machine capable of performing rapid and efficient dialysis on dialysis patients, and the key point is the development of an efficient adsorbent. In addition, there is also an urgent need for the development of a material capable of efficiently and rapidly removing toxins from dialysate and restoring electrolyte concentration in response to the reuse of dialysate. Therefore, it is becoming more and more important to develop an adsorbent having a function of rapidly and efficiently adsorbing toxic substances in a dialysis process. This is also one of the development directions for the development of small hemodialysis machines and the reuse of dialysate in the future.
Hydrogen-bonded organic framework materials (HOFs) are crystalline porous framework materials formed by organic building blocks connected by hydrogen bonds. In addition to hydrogen bonding, other intermolecular forces such as pi-pi, electrostatic and van der waals forces play a very important role in the construction and stability of HOFs. Similar to MOFs/COFs, HOFs also have the characteristics of large specific surface area, various structures, adjustable pore channel shape and size, modifiable pore surface and the like. However, because HOFs are constructed by hydrogen bonds, and the acting force of the hydrogen bonds is generally weaker than the strength and the reversibility of coordination bonds or covalent bonds, the HOFs material has some unique advantages: (1) the preparation conditions of the HOFs are milder; (2) HOFs have better solution processability; (3) the HOFs material has better self-healing capability and regeneration capability; (4) since most of the HOFs materials do not contain metal ions, this metal-free property gives the HOFs materials better biocompatibility and lower cytotoxicity, so that the HOFs show great application potential in biological applications. At present, the growth time of the HOFs material is long, the growth time of the HOFs material can be obviously shortened under the action of an electric field, and the crystal form of the HOFs material is not changed, so that a new thought is provided for shortening the growth time of the HOFs material.
The invention content is as follows:
the invention aims to rapidly prepare a hydrogen bond organic framework material by using an external electric field method, and the hydrogen bond organic framework material is used for rapidly and efficiently removing small and medium molecular toxins in the hemodialysis process. In order to achieve the 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:
(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 certain voltage into the solution mixed with the organic ligand, centrifuging and washing the product for multiple times after reacting for certain time, and drying 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 dispersed uniformly by ultrasonic or stirring.
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 rotation 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 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 to remove toxins from hemodialysis.
Preferably, the toxins include both medium molecule toxins and small molecule toxins.
Preferably, the medium molecular toxin is represented by lysozyme and the small molecular toxin is represented by urea.
As mentioned above, the method for rapidly preparing the hydrogen bond organic framework material based on the electric field and the application thereof have the following beneficial effects:
(1) the deprotonation of the carboxyl on the ligand is accelerated under the promotion action of an electric field, the hydrogen bond organic framework material constructed based on the 1, 3, 6, 8-tetra (6-carboxynaphthalene) pyrene ligand is obtained in a short time by utilizing the synergistic action of multiple hydrogen bonds between the carboxyl on the ligand and pi-pi interaction force between pyrene, and the material has the characteristics of maximum aperture and specific surface area in the existing hydrogen bond organic framework material, permanent pore channels, high chemical and thermal stability, mild synthesis conditions, short synthesis time and the like, and the preparation method of the material is simple and has strong operability.
(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 small and medium molecular toxins. The adsorption amount of the hydrogen bond organic framework material to the urea is about 40mg/g, and the clearance rate is about 60 percent. The adsorption amount of the hydrogen bond organic framework material to the lysozyme is about 30mg/g, and the clearance rate reaches 80 percent. 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 clearing hemodialysis toxin.
Description of the drawings:
FIG. 1(a) is the chemical structural formula of the organic ligand described in example 1 of the present invention, and (b) is the structural schematic diagram of the hydrogen bonding organic framework material described in example 1 of the present invention;
FIG. 2 is a simulated XRD spectrum and a powder XRD spectrum of the hydrogen bonding organic framework material according to example 1 of the present invention;
FIG. 3 is a scanning electron micrograph of a hydrogen bonding organic framework material according to example 1 of the present invention;
fig. 4 shows the results of the experiment of adsorbing urea by hydrogen bond organic framework material in example 1 of the present invention, (a) shows the adsorption amounts of hydrogen bond organic framework material with the same content to urea at different adsorption times, and (b) shows the removal efficiency of hydrogen bond organic framework material with different content to urea;
FIG. 5 shows the results of the adsorption experiment of the hydrogen bond organic framework material on lysozyme in example 1 of the present invention, wherein (a) shows the adsorption amounts of the hydrogen bond organic framework materials with the same content on lysozyme at different adsorption times, and (b) shows the removal efficiencies of the hydrogen bond organic framework materials with different contents on lysozyme;
the specific implementation scheme is as follows:
the embodiments of the present invention are described below by way of specific examples, which are intended to illustrate the invention and not to limit the scope of the invention. Unless otherwise specified, the technical means used in the present invention are 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 weighed and added to a beaker containing the organic ligand, and dispersed by sonication until the organic ligand was completely dissolved.
(2) A measured 80mL of acetone was added to the beaker with stirring at 300 rpm. The rotation speed is adjusted to 50 revolutions per minute, and 25V direct current is introduced into the beaker by using a direct current power supply, and the electrifying time is 4 hours.
(3) The product was separated by centrifugation at 8000 rpm for 7 minutes and washed with 30mL of acetone, centrifuged again and repeated three times. The obtained hydrogen bond organic framework material is dried in vacuum at the temperature of 60 ℃, and the yield is 82.8%.
Example 2:
(1) 200mg of 1, 3, 6, 8-tetrakis (6-carboxynaphthalene) pyrene was weighed and added to a beaker, and 50mL of N, N' -dimethylformamide was added to the beaker with the organic ligand and dispersed by sonication until the organic ligand was completely dissolved.
(2) A measured amount of 240mL of acetone was added to the beaker with stirring at 400 rpm. The rotation speed is adjusted to 50 revolutions per minute, and 70V direct current is introduced into the beaker by using a direct current power supply, and the electrifying time is 2 hours.
(3) The product was separated by centrifugation at 8000 rpm for 7 minutes and washed with 50mL of acetone, centrifuged again and repeated three times. The obtained hydrogen bond organic framework material is dried in vacuum at the temperature of 60 ℃, and the yield is 85.4%.
Example 3:
(1) 100mg of 1, 3, 6, 8-tetra (6-carboxynaphthalene) pyrene was weighed and added to a beaker, and 20mL of dimethyl sulfoxide was added to the beaker with the organic ligand and dispersed by ultrasound until the organic ligand was completely dissolved.
(2) A measured amount of 60mL of tetrahydrofuran was added to the beaker with stirring at 400 rpm. The rotating speed is adjusted to 50 revolutions per minute, and a direct current power supply is used for introducing 50V direct current into the beaker, wherein the electrifying time is 3 hours.
(3) The product was separated by centrifugation at 8000 rpm for 7 minutes, washed with 40mL of acetone, centrifuged again and repeated three times. The obtained hydrogen bond organic framework material is dried in vacuum at the temperature of 60 ℃, and the yield is 79.5%.
Performance testing
FIG. 1 is a schematic structural diagram of a hydrogen bonding organic framework material prepared by an external electric field in example 1, where (a) is a chemical structural formula of an organic ligand, and (b) is a schematic structural diagram of the hydrogen bonding organic framework material. From FIG. 1, the two-dimensional pore channel size of the hydrogen bonding organic framework material is shown as
FIG. 2 is a simulated XRD spectrum and a powder XRD spectrum of the hydrogen bonding organic framework material prepared by the applied electric field in example 1. As can be seen from FIG. 2, the hydrogen bond organic framework material prepared by using the external electric field has better pure phase degree, and can well maintain the crystallinity.
FIG. 3 is a scanning electron micrograph of the hydrogen bonding organic framework material prepared by an applied electric field in example 1. As is clear from fig. 3, the hydrogen bonding organic framework material has a rod-like shape.
Fig. 4 shows the results of the experiment of adsorbing urea by the hydrogen bond organic framework material prepared by the applied electric field in example 1, where (a) is the adsorption amount of the hydrogen bond organic framework material to urea at different adsorption times, and (b) is the removal efficiency of urea by the hydrogen bond organic framework material with different contents. As can be seen from FIG. 4, when the adsorption time is 30 minutes, the adsorption amount of the hydrogen bonding organic framework material to urea reaches a maximum value, which is about 40mg/g, indicating that the hydrogen bonding organic framework material has the performance of fast adsorption to urea and the removal rate is about 60%.
FIG. 5 shows the results of the adsorption experiment of the hydrogen bond organic framework material prepared by the applied electric field on lysozyme in example 1, wherein (a) shows the adsorption amount of the hydrogen bond organic framework material on lysozyme in different adsorption times, and (b) shows the removal efficiency of the hydrogen bond organic framework material with different addition amounts on lysozyme. As can be seen from FIG. 5, when the adsorption time is only 10min, the adsorption amount of the hydrogen bond organic framework material to lysozyme is already maximized, which is about 30mg/g, indicating that the hydrogen bond organic framework material also has a rapid adsorption function to lysozyme and the removal rate thereof can reach 80%.
Claims (8)
1. A method for rapidly preparing a hydrogen bond organic framework material based on an electric field and an application thereof are characterized by comprising the following steps:
(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 certain voltage into the solution mixed with the organic ligand, centrifuging and washing the product for multiple times after reacting for certain time, and drying to obtain the product.
2. The method for rapidly preparing the hydrogen bond organic framework material based on the electric field according to the claim 1, which is characterized in that: 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.
3. The method for rapidly preparing the hydrogen bond organic framework material based on the electric field according to the claim 1, which is characterized in that: in the step (2), the adding amount of the organic ligand is 10-400 mg, and the mass-volume ratio of the organic ligand to the organic solvent is 1: 2-2: 1 (mg: mL).
4. The method for rapidly preparing the hydrogen bond organic framework material based on the electric field according to the claim 1, which is characterized in that: the dissolution in the step (2) can be rapidly and uniformly dispersed by an ultrasonic or stirring method.
5. The method for rapidly preparing the hydrogen bond organic framework material based on the electric field according to the claim 1, which is characterized in that: in the step (3), the applied voltage is 0-90V, and the reaction time is 0-6 h.
6. The method for rapidly preparing the hydrogen bond organic framework material based on the electric field according to the claim 1, which is characterized in that: the rotation 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 ℃.
7. The application of the method for rapidly preparing the hydrogen bond organic framework material based on the electric field according to the claims 1-6 is characterized in that: the hydrogen bond organic framework material can be used for quickly and efficiently removing small and medium molecular toxins in the hemodialysis process.
8. The application of the method for rapidly preparing the hydrogen bond organic framework material based on the electric field according to the claim 7 is characterized in that: before the hemodialysis process, the hydrogen bond organic framework material is activated for 5-20 hours 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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