CN112110947A - Preparation method of ionic liquid modified phenylboronic acid for separating glycoprotein - Google Patents
Preparation method of ionic liquid modified phenylboronic acid for separating glycoprotein Download PDFInfo
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- 102000003886 Glycoproteins Human genes 0.000 title claims abstract description 44
- 108090000288 Glycoproteins Proteins 0.000 title claims abstract description 44
- 239000002608 ionic liquid Substances 0.000 title claims abstract description 40
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 27
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000009210 therapy by ultrasound Methods 0.000 claims abstract description 17
- PDNOURKEZJZJNZ-UHFFFAOYSA-N [4-(bromomethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(CBr)C=C1 PDNOURKEZJZJNZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 11
- 238000001291 vacuum drying Methods 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims description 13
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 17
- 238000000926 separation method Methods 0.000 abstract description 13
- 230000009881 electrostatic interaction Effects 0.000 abstract description 3
- 230000002209 hydrophobic effect Effects 0.000 abstract description 3
- 230000003993 interaction Effects 0.000 abstract description 3
- 238000001179 sorption measurement Methods 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 12
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 10
- 239000004327 boric acid Substances 0.000 description 10
- 102000004856 Lectins Human genes 0.000 description 5
- 108090001090 Lectins Proteins 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 239000002523 lectin Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 238000000527 sonication Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000001042 affinity chromatography Methods 0.000 description 2
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 2
- 230000013595 glycosylation Effects 0.000 description 2
- 238000006206 glycosylation reaction Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 208000027205 Congenital disease Diseases 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 238000001386 capillary affinity electrophoresis Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000005714 functional activity Effects 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000007885 magnetic separation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002482 oligosaccharides Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/145—Extraction; Separation; Purification by extraction or solubilisation
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- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Medicinal Chemistry (AREA)
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- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
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Abstract
The invention discloses a preparation method of ionic liquid modified phenylboronic acid for separating glycoprotein, which specifically comprises the following steps: step 1, dissolving 4- (bromomethyl) phenylboronic acid in ethyl acetate, and performing ultrasonic treatment to obtain a solution A; step 2, adding 1-vinyl imidazole into the solution A obtained in the step 1, and performing ultrasonic treatment to obtain a solution B; step 3, reacting the obtained solution B at 50-75 ℃ for 12-24 h; and 4, adding diethyl ether into the mixture obtained in the step 3, performing rotary evaporation to obtain a product A, and performing vacuum drying on the product A to obtain the product A. The invention is based on the non-directional electrostatic interaction and the hydrophobic interaction generated between the ionic liquid and the glycoprotein, thereby increasing the adsorption capacity and improving the separation performance of the material.
Description
Technical Field
The invention belongs to the technical field of glycoprotein separation, and relates to a preparation method of ionic liquid modified phenylboronic acid for separating glycoprotein.
Background
Glycoproteins are proteins composed of oligosaccharide chains and polypeptide chains covalently linked to each other, and play important roles in physiological activities such as immunity, blood coagulation, signal transmission, and cell growth and differentiation. Glycosylation of proteins is closely related to folding, stability, and functional activity of proteins, and irregularities in glycosylation can lead to the development of cancer, inflammatory diseases, and congenital diseases. However, since the abundance of glycoproteins in biological samples is low, the structure is complex and various, and when the structure and the function of glycoproteins are analyzed, the separation and the enrichment of target glycoproteins are often needed. Therefore, it is of great significance to develop a rapid, efficient, and highly specific method for separating glycoproteins.
Common glycoprotein isolation methods include lectin affinity chromatography, capillary electrophoresis, and boronic acid affinity. The lectin affinity chromatography is to divide the glycoprotein into different components according to the strength of the affinity of the glycoprotein and the lectin, has high separation and enrichment efficiency, but because the lectin is also the glycoprotein, the lectin aiming at the target glycoprotein has high cost, complex operation, long time consumption, poor solvent tolerance and difficult storage. The capillary electrophoresis method drives each component of the point-carrying particles to migrate in the capillary at different speeds through a high-voltage electric field, and is simple, efficient and automatic. But the single sampling amount is low, the enrichment efficiency is low, and the method is more suitable for determining the purity and the molecular weight of the glycoprotein.
The glycoprotein separation and enrichment method based on boric acid utilizes the reversible binding property of boric acid and cis-diol: under alkaline conditions, the boric acid is tetragonal sp3Structure capable of forming reversible covalent bond with cis-diol; under acidic conditions, the boric acid is triangular sp2Structure, the binding to cis-diol is significantly reduced. The method can effectively separate glycoprotein by adjusting pH and adopting a boric acid affinity method, has the advantages of simple and rapid operation, low cost, environmental friendliness and the like, and is widely concerned in glycoprotein separation. The preparation of novel boric acid functionalized materials with better separation effect is one of the hot directions of the current glycoprotein separation research.
Ionic Liquids (ILs) are molten salts having a melting point of 100 ℃ or less, which are formed by combining cations and anions, and have the characteristics of easy volatilization, good thermal stability, structure adjustability and the like. In particular, since the ionic liquid and the glycoprotein form directional hydrogen bonds and pi-pi stacking, thereby enhancing selectivity and recognition capability, the ionic liquid with good biocompatibility has been applied to the preparation of glycoprotein separation and enrichment materials. Therefore, the ionic liquid modified phenylboronic acid material prepared by the method has a good application prospect in separation of glycoprotein.
Disclosure of Invention
The invention aims to provide a preparation method of ionic liquid modified phenylboronic acid for separating glycoprotein, which is based on the fact that non-directional electrostatic interaction and hydrophobic interaction are generated between ionic liquid and glycoprotein, so that adsorption capacity is improved, and separation performance of materials is improved.
The technical scheme adopted by the invention is that the preparation method of the ionic liquid modified phenylboronic acid for separating glycoprotein specifically comprises the following steps:
step 1, dissolving 4- (bromomethyl) phenylboronic acid in ethyl acetate, and performing ultrasonic treatment to obtain a solution A;
step 2, adding 1-vinyl imidazole into the solution A obtained in the step 1, and performing ultrasonic treatment to obtain a solution B;
and 4, adding diethyl ether into the mixture obtained in the step 3, performing rotary evaporation to obtain a product A, and performing vacuum drying on the product A to obtain the product A.
The present invention is also characterized in that,
in the step 1, the dosage of the 4- (bromomethyl) phenylboronic acid is 2-3 mmol; the dosage of the ethyl acetate is 10-25 mL.
In the step 1 and the step 2, the ultrasonic treatment time is 30-60 min.
In the step 2, the dosage of the 1-vinyl imidazole is 2.5-3.5 mmol.
In step 3, 4- (bromomethyl) phenylboronic acid and 1-vinylimidazole are reacted in N2And carrying out alkylation reaction under the atmosphere.
In the step 4, the rotary evaporation temperature is 30-70 ℃.
The ionic liquid has the advantages of recoverability, conductivity, excellent mechanical property and biocompatibility. Non-directional electrostatic interaction and hydrophobic interaction are generated between the ionic liquid and the glycoprotein, so that the adsorption capacity is increased, and directional hydrogen bonds and pi-pi accumulation are formed between the ionic liquid and the glycoprotein, so that the selectivity and the recognition capacity are enhanced, and the material separation performance is improved. The defects of easy swelling, insufficient mechanical stability, low specific surface area and low permeability of the organic solvent of the existing boric acid organic integral material are overcome; the problems of complex preparation process and poor pH stability of the boric acid inorganic integral material; the magnetic separation material is easy to agglomerate, and the biocompatibility is not good.
Drawings
FIG. 1 is a 1H NMR spectrum of an ionic liquid functionalized phenylboronic acid material prepared by the preparation method of the ionic liquid modified phenylboronic acid for separating glycoprotein according to the invention;
FIG. 2 is an FT-IR spectrogram of an ionic liquid functionalized phenylboronic acid material prepared by the preparation method of the ionic liquid modified phenylboronic acid for separating glycoprotein.
Detailed Description
The present invention will be described in detail below with reference to the accompanying drawings and specific embodiments.
The invention relates to a preparation method of ionic liquid modified phenylboronic acid for separating glycoprotein, which specifically comprises the following steps:
step 1, dissolving 4- (bromomethyl) phenylboronic acid in ethyl acetate, and performing ultrasonic treatment to obtain a solution A;
in the step 1, the dosage of the 4- (bromomethyl) phenylboronic acid is 2-3 mmol; the dosage of the ethyl acetate is 10-25 mL. The ultrasonic treatment time is 30-60 min.
Step 2, adding 1-vinyl imidazole into the solution A obtained in the step 1, and performing ultrasonic treatment to obtain a solution B; the dosage of the 1-vinyl imidazole is 2.5-3.5 mmol. The ultrasonic treatment time is 30-60 min.
And 4, adding diethyl ether into the mixture obtained in the step 3, performing rotary evaporation at the temperature of 30-70 ℃, obtaining a product A after the liquid is completely evaporated, and performing vacuum drying on the product A to obtain the catalyst. The vacuum drying temperature is 50 ℃, and the drying time is 12 h.
The synthetic route of the ionic liquid functionalized phenylboronic acid material prepared by the preparation method of the ionic liquid modified phenylboronic acid for separating glycoprotein is as follows:
example 1
Step 1, 2mmol of 4- (bromomethyl) phenylboronic acid was dissolved in 10mL of ethyl acetate and mixed by sonication for 30 min. Solution a was obtained.
And 2, adding 2.5mmol of 1-vinylimidazole into the solution A obtained in the step 1, and performing ultrasonic treatment for 30min to uniformly mix to obtain a solution B.
And 4, adding 30mL of diethyl ether into the mixture obtained in the step 3 after the reaction is finished, then carrying out rotary evaporation at 30 ℃, and carrying out vacuum drying on the product at 50 ℃ for 12h to obtain the final product.
Example 2
Step 1, 3mmol4- (bromomethyl) phenylboronic acid was dissolved in 25mL ethyl acetate and mixed well by sonication for 60 min. Solution a was obtained.
And 2, adding 3.5mmol 1-vinyl imidazole into the solution A obtained in the step 1, and performing ultrasonic treatment for 60min to uniformly mix to obtain a solution B.
And 4, adding 50mL of diethyl ether into the mixture obtained in the step 3 after the reaction is finished, then carrying out rotary evaporation at 70 ℃, and carrying out vacuum drying on the product at 50 ℃ for 12h to obtain the final product.
Example 3
Step 1, 2.5mmol4- (bromomethyl) phenylboronic acid was dissolved in 20mL ethyl acetate and sonicated for 40min to allow uniform mixing. Solution a was obtained.
And 2, adding 3.0mmol of 1-vinylimidazole into the solution A obtained in the step 1, and performing ultrasonic treatment for 40min to uniformly mix to obtain a solution B.
And 4, adding 45mL of diethyl ether into the mixture obtained in the step 3 after the reaction is finished, then carrying out rotary evaporation at 50 ℃, and carrying out vacuum drying on the product at 50 ℃ for 12h to obtain the final product.
Example 4
Step 1, 2.5mmol of 4- (bromomethyl) phenylboronic acid was dissolved in 20mL of ethyl acetate and mixed by sonication for 30 min. Solution a was obtained.
And 2, adding 2.5mmol of 1-vinylimidazole into the solution A obtained in the step 1, and performing ultrasonic treatment for 30min to uniformly mix to obtain a solution B.
And 4, adding 30mL of diethyl ether into the mixture obtained in the step 3 after the reaction is finished, then carrying out rotary evaporation at 45 ℃, and carrying out vacuum drying on the product at 50 ℃ for 12h to obtain the final product.
Example 5
Step 1, 3mmol4- (bromomethyl) phenylboronic acid was dissolved in 25mL ethyl acetate and sonicated for 60min to allow uniform mixing. Solution a was obtained.
And 2, adding 2.5mmol of 1-vinylimidazole into the solution A obtained in the step 1, and performing ultrasonic treatment for 60min to uniformly mix to obtain a solution B.
And 4, adding 50mL of diethyl ether into the mixture obtained in the step 3 after the reaction is finished, then carrying out rotary evaporation at 50 ℃, and carrying out vacuum drying on the product at 50 ℃ for 12h to obtain the final product.
The preparation method of the ionic liquid modified phenylboronic acid for separating glycoprotein is characterized by comprising the following steps of:
1. the process for preparing the ionic liquid functionalized phenylboronic acid material is simple to operate, safe and environment-friendly, and good in biocompatibility of the material;
2. 1-vinyl imidazole functionalized 4- (bromomethyl) phenylboronic acid is used, so that the selectivity and the recognition capability can be enhanced, and the material separation performance can be improved;
3. under alkaline conditions, the boric acid is tetragonal sp3Structure capable of forming reversible covalent bond with glycoprotein; under acidic conditions, the boric acid is triangular sp2Structure, dissociation occurs. Glycoprotein can be separated simply and effectively by simply adjusting pH.
The 1H NMR spectrum of the ionic liquid functionalized phenylboronic acid material prepared by the preparation method of the ionic liquid modified phenylboronic acid for separating glycoprotein is shown in figure 1, wherein 1H NMR (600MHz,20 ℃, DMSO) is 7.4(1H),7.85(2H),5.53(2H),8.15(1H),8.31(1H),9.8(1H),5.44(1H) and 6.01 (1H);
the FT-IR spectrum of the ionic liquid functionalized phenylboronic acid material prepared by the preparation method of the ionic liquid modified phenylboronic acid for separating glycoprotein is shown in figure 2, and the infrared spectra of the product and 1-vinyl imidazole respectively have absorption bands at 1614, 1360 and 960cm-1, which respectively correspond to C-N, C-N and C-H stretching vibration of imidazole rings. The product and 4- (bromomethyl) phenylboronic acid both exhibited absorption bands at 1345, 1470cm-1, corresponding to B-O and C-B tensile vibrations, respectively.
Claims (6)
1. A preparation method of ionic liquid modified phenylboronic acid for separating glycoprotein is characterized by comprising the following steps: the method specifically comprises the following steps:
step 1, dissolving 4- (bromomethyl) phenylboronic acid in ethyl acetate, and performing ultrasonic treatment to obtain a solution A;
step 2, adding 1-vinyl imidazole into the solution A obtained in the step 1, and performing ultrasonic treatment to obtain a solution B;
step 3, reacting the obtained solution B at 50-75 ℃ for 12-24 h;
and 4, adding diethyl ether into the mixture obtained in the step 3, performing rotary evaporation to obtain a product A, and performing vacuum drying on the product A to obtain the product A.
2. The method for preparing ionic liquid modified phenylboronic acid for separating glycoprotein according to claim 1, wherein the ionic liquid modified phenylboronic acid comprises: the dosage of the 4- (bromomethyl) phenylboronic acid in the step 1 is 2-3 mmol; the dosage of the ethyl acetate is 10-25 mL.
3. The method for preparing ionic liquid modified phenylboronic acid for separating glycoprotein according to claim 1, wherein the ionic liquid modified phenylboronic acid comprises: in the step 1 and the step 2, the time of ultrasonic treatment is 30-60 min.
4. The method for preparing ionic liquid modified phenylboronic acid for separating glycoprotein according to claim 1, wherein the ionic liquid modified phenylboronic acid comprises: in the step 2, the dosage of the 1-vinyl imidazole is 2.5-3.5 mmol.
5. The method for preparing ionic liquid modified phenylboronic acid for separating glycoprotein according to claim 1, wherein the ionic liquid modified phenylboronic acid comprises: in the step 3, 4- (bromomethyl) phenylboronic acid and 1-vinyl imidazole are in N2And carrying out alkylation reaction under the atmosphere.
6. The method for preparing ionic liquid modified phenylboronic acid for separating glycoprotein according to claim 1, wherein the ionic liquid modified phenylboronic acid comprises: and in the step 4, the rotary evaporation temperature is 30-70 ℃.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114560970A (en) * | 2022-03-18 | 2022-05-31 | 陕西科技大学 | Ion-conductive hydrogel and preparation method and application thereof |
| CN114920891A (en) * | 2022-05-16 | 2022-08-19 | 嘉兴学院 | Magnetic boron affinity polyion liquid and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106432087A (en) * | 2016-09-06 | 2017-02-22 | 山东师范大学 | Triphase catalyst UiO-67-IM and preparation method and application thereof |
| CN108640906A (en) * | 2018-04-03 | 2018-10-12 | 山东师范大学 | A kind of dual-function composite catalyst and the preparation method and application thereof |
| CN108841008A (en) * | 2018-06-27 | 2018-11-20 | 首都师范大学 | A kind of preparation of the Solid-State proton conductive material with wide operating temperature range |
-
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106432087A (en) * | 2016-09-06 | 2017-02-22 | 山东师范大学 | Triphase catalyst UiO-67-IM and preparation method and application thereof |
| CN108640906A (en) * | 2018-04-03 | 2018-10-12 | 山东师范大学 | A kind of dual-function composite catalyst and the preparation method and application thereof |
| CN108841008A (en) * | 2018-06-27 | 2018-11-20 | 首都师范大学 | A kind of preparation of the Solid-State proton conductive material with wide operating temperature range |
Non-Patent Citations (1)
| Title |
|---|
| MOUSLIM MESSALI: "An efficient and green sonochemical synthesis of some new eco-friendly functionalized ionic liquids" * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114560970A (en) * | 2022-03-18 | 2022-05-31 | 陕西科技大学 | Ion-conductive hydrogel and preparation method and application thereof |
| CN114920891A (en) * | 2022-05-16 | 2022-08-19 | 嘉兴学院 | Magnetic boron affinity polyion liquid and preparation method and application thereof |
| CN114920891B (en) * | 2022-05-16 | 2023-08-01 | 嘉兴学院 | Magnetic boron-affinity polyion liquid and preparation method and application thereof |
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