CN109134875A - L-menthol is the preparation of the chiral covalent organic framework material of chiral source - Google Patents
L-menthol is the preparation of the chiral covalent organic framework material of chiral source Download PDFInfo
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- CN109134875A CN109134875A CN201810979725.8A CN201810979725A CN109134875A CN 109134875 A CN109134875 A CN 109134875A CN 201810979725 A CN201810979725 A CN 201810979725A CN 109134875 A CN109134875 A CN 109134875A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 title claims description 15
- 239000013310 covalent-organic framework Substances 0.000 title claims description 11
- 239000000463 material Substances 0.000 title description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims abstract description 32
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims abstract description 16
- 239000012043 crude product Substances 0.000 claims abstract description 13
- CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 claims abstract description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 239000013078 crystal Substances 0.000 claims abstract description 7
- 239000007787 solid Substances 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 7
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 239000002994 raw material Substances 0.000 claims abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 238000002390 rotary evaporation Methods 0.000 claims description 15
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 239000000741 silica gel Substances 0.000 claims description 9
- 229910002027 silica gel Inorganic materials 0.000 claims description 9
- 239000003480 eluent Substances 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 4
- -1 2,5- dibromo chlorobenzoyl chloride Chemical compound 0.000 claims description 3
- SQQKOTVDGCJJKI-UHFFFAOYSA-N 2,5-dibromobenzoic acid Chemical compound OC(=O)C1=CC(Br)=CC=C1Br SQQKOTVDGCJJKI-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 235000015320 potassium carbonate Nutrition 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- RQEUFEKYXDPUSK-ZETCQYMHSA-N (1S)-1-phenylethanamine Chemical compound C[C@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-ZETCQYMHSA-N 0.000 abstract 2
- 238000006555 catalytic reaction Methods 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- SFTFNJZWZHASAQ-UHFFFAOYSA-N 3,5-dibromobenzoic acid Chemical compound OC(=O)C1=CC(Br)=CC(Br)=C1 SFTFNJZWZHASAQ-UHFFFAOYSA-N 0.000 abstract 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 238000007039 two-step reaction Methods 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000006416 CBr Chemical group BrC* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
Classifications
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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
-
- 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
- B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
- B01J20/226—Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses one kind using (s)-(-)-α-phenylethylamine as the preparation method of the dissaving polymer of chiral source: with thionyl chloride, 3,5- dibromobenzoic acid and (S)-(-)-α-phenylethylamine are raw material, by two step organic synthesis, white needle-like crystals A is made；With 1,3,5- tribromo-benzene, Pd (PPh3) 2Cl2, CuI, PPh3 and trimethylsilyl acetylene for raw material, compound B is synthesized through two-step reaction；Using A, B, Pd (PPh3) 2Cl2, PPh3, CuI as raw material, triethylamine and dimethylformamide are that solvent using microwave reactor heating stirring 17 minutes obtained yellow solid, and test product after the purified drying of crude product.The resulting Performances of Novel Nano-Porous meter level dissaving polymer of the present invention is in asymmetric catalysis, it is possible to provide largely containing the active site of chiral radicals, improves asymmetric catalysis synthesis catalytic efficiency.
Description
Technical field
The invention belongs to high molecular materials and engineering field, in particular to covalently organic using l-menthol as the chirality of chiral source
The preparation method of skeleton.
Background technique
Chiral resolution is significant, and the different isomer of optical activity, often there were significant differences for its property.However it is natural
Chiral material nature it is actually rare, existing technology and traditional process means easily cause serious pollution to environment, because
This, a kind of novel porous material that can be used for chiral resolution is prepared with important scientific meaning and researching value.
Summary of the invention
The purpose of the present invention is to provide a kind of using l-menthol as the preparation method of the covalent organic framework of chiral source,
Containing chiral structure and appearance structure uniqueness is tubulose, which can be used for chiral resolution, have biggish development prospect.
The purpose of the present invention is achieved through the following technical solutions: a kind of covalently having using l-menthol as chiral source
The step of preparation method of machine skeleton, the method, is as follows:
(1) under nitrogen protection state, by thionyl chloride (13.5mL) injection equipped with 2,5- dibromobenzoic acid (3.00g,
In three-necked bottle 9.26mmol), it is stirred to react 4 hours by oil bath heating to 75 DEG C, obtaining compound through rotary evaporation is 2,
5- dibenzoyl chlorine；
(2) under nitrogen protection state, l-menthol (2.89g, 18.5mmol) injection is equipped with 2,5- dibromo chlorobenzoyl chloride
In the three-necked bottle of (1.69g, 8.33mmol), toluene (15.0mL) is solvent, and 110 DEG C are reacted 16 hours, and rotary evaporation is removed
The crude product of toluene is purified (R through silica gel chromatographic columnf=0.44, eluent are as follows: n-hexane/ethyl acetate=20:1), rotation
Evaporation obtains white crystal A；
(3) by 1,3,5- tribromo-benzene (5.00g, 15.9mmol), Pd (PPh3) 2Cl2 (340mg, 0.490mmol), CuI
(90.0mg, 0.490mmol), PPh3 (129mg, 0.490mmol) are put into three-neck flask, carry out nitrogen protection, and 176mL is added
Triethylamine as solvent, after reaction 15 minute, 9.00mL trimethylsilyl acetylene is added, react 16 hours at 90 DEG C, thick production
Object is purified (R through silica gel chromatographic columnf=0.42, eluent is n-hexane), rotary evaporation obtains faint yellow concentrated solution, cooling
Having crystal to be precipitated is compound 1,3,5- tri- (trimethylsilyl acetylene base) benzene；
(4) by 1,3,5- tri- (trimethylsilyl acetylene base) benzene (1.00g, 2.73mmol) and K2CO3 (57.0mg, 0.410mmol)
It is added in three-necked bottle, carries out nitrogen protection.14.4mL tetrahydrofuran and 4.30mL methanol are added, is stirred at room temperature 6 hours, is passed through
Filter, rotary evaporation remove tetrahydrofuran and methanol solvate, and crude product is purified (R through silica gel chromatographic columnf=0.56, eluent
Are as follows: n-hexane), yellow solid B is obtained after rotary evaporation；
(5) by A(600mg, 1.00mmol), B(94.7mg, 0.631mmol), Pd (PPh3) 2Cl2(65.1mg,
0.0940mmol), PPh3 (114mg, 0.438mmol), CuI(68.1mg, 0.371mmol) it is added in three-necked bottle, in nitrogen
Under protection, 50.0mL triethylamine is injected, is reacted 18 hours at 90 DEG C, obtains crude product, then uses methanol, KI aqueous solution, three respectively
Chloromethanes washs crude product, obtains brown solid after drying.
Beneficial effects of the present invention: it can be used for the chirality of racemic modification using l-menthol as the covalent organic framework of chiral source
In fractionation, make the high-efficient of chiral resolution, low energy consumption.
Detailed description of the invention
Fig. 1 is using l-menthol as the infrared spectrum of the covalent organic framework of chiral source.
3448cm-1(characteristic peak generated due to hydrogen bond action)；2951cm-1(CH3Stretching vibration)； 2202cm-1(C
The stretching vibration of ≡ C)； 1725cm-1(C=O stretching vibration of ester group)；1583cm-1(the double bond stretching vibration of aromatic ring)；
1233cm-1(the C-O stretching vibration of ester group)；547cm-1(stretching vibration of C-Br).
Fig. 2 is using l-menthol as the scanning electron microscope (SEM) photograph of the covalent organic framework of chiral source.
It can be observed that the smooth tubulose of polygon and surface is presented in chiral covalent organic framework from SEM figure, this be by
It is conjugated polymer in polymer, and phenyl ring generates stronger π-π superposition and polymer crystallization is caused to work well, and is formed
Special tubular morphology.
Specific embodiment
In order to which objects and advantages of the present invention are more clearly understood, the present invention is carried out below in conjunction with example further detailed
It describes in detail bright.It should be appreciated that specific example described herein is only used to explain the present invention, it is not intended to limit the present invention.
Specific implementation of the invention is as follows: using l-menthol as the preparation method of the chiral covalent organic framework of chiral source,
The step of the method, is as follows:
(1) under nitrogen protection state, by thionyl chloride (13.5mL) injection equipped with 2,5- dibromobenzoic acid (3.00g,
In three-necked bottle 9.26mmol), it is stirred to react 4 hours by oil bath heating to 75 DEG C, obtaining compound through rotary evaporation is 2,
5- dibenzoyl chlorine；
(2) under nitrogen protection state, l-menthol (2.89g, 18.5mmol) injection is equipped with 2,5- dibromo chlorobenzoyl chloride
In the three-necked bottle of (1.69g, 8.33mmol), toluene (15.0mL) is solvent, and 110 DEG C are reacted 16 hours, and rotary evaporation is removed
The crude product of toluene is purified (R through silica gel chromatographic columnf=0.44, eluent are as follows: n-hexane/ethyl acetate=20:1), revolving
Obtain white crystal A；
(3) by 1,3,5- tribromo-benzene (5.00g, 15.9mmol), Pd (PPh3) 2Cl2 (340mg, 0.490mmol), CuI
(90.0mg, 0.490mmol), PPh3 (129mg, 0.490mmol) are put into three-neck flask, carry out nitrogen protection, and 176mL is added
Triethylamine as solvent, after reaction 15 minute, 9.00mL trimethylsilyl acetylene is added, is reacted 16 hours at 90 DEG C.It is thick to produce
Object is purified (R through silica gel chromatographic columnf=0.42, eluent is n-hexane), rotary evaporation obtains faint yellow concentrated solution, cooling
Having crystal to be precipitated is compound 1,3,5- tri- (trimethylsilyl acetylene base) benzene；
(4) by 1,3,5- tri- (trimethylsilyl acetylene base) benzene (1.00g, 2.73mmol) and K2CO3 (57.0mg, 0.410mmol)
It is added in three-necked bottle, carries out nitrogen protection.14.4mL tetrahydrofuran and 4.30mL methanol are added, is stirred at room temperature 6 hours.By
Filter, rotary evaporation remove tetrahydrofuran and methanol solvate, and crude product is purified (R through silica gel chromatographic columnf=0.56 lotion are as follows:
N-hexane), yellow solid B is obtained after rotary evaporation；
(5) by A(600mg, 1.00mmol), B(94.7mg, 0.631mmol), Pd (PPh3) 2Cl2(65.1mg,
0.0940mmol), PPh3 (114mg, 0.438mmol), CuI(68.1mg, 0.371mmol) it is added in three-necked bottle, in nitrogen
Under protection, 50.0mL triethylamine is injected, is reacted 18 hours at 90 DEG C, obtains crude product, then uses methanol, KI aqueous solution, three respectively
Chloromethanes washs crude product, obtains brown solid after drying.
This is embodied resulting novel using l-menthol as the chiral covalent organic framework of chiral source, contains chiral structure
With unique tubular morphology, the new material of chiral resolution can be used as.
The above is only a preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, without departing from the principle of the present invention, it can also make several improvements and retouch, these improvements and modifications are also answered
It is considered as protection scope of the present invention.
Claims (2)
1. using l-menthol as the preparation method of the chiral covalent organic framework of chiral source, which is characterized in that the step of the method
It is rapid as follows:
(1) under nitrogen protection state, by thionyl chloride (13.5mL) injection equipped with 2,5- dibromobenzoic acid (3.00g,
In three-necked bottle 9.26mmol), it is stirred to react 4 hours by oil bath heating to 75 DEG C, obtaining compound through rotary evaporation is 2,
5- dibenzoyl chlorine；
(2) under nitrogen protection state, l-menthol (2.89g, 18.5mmol) injection is equipped with 2,5- dibromo chlorobenzoyl chloride
In the three-necked bottle of (1.69g, 8.33mmol), toluene (15mL) is solvent, and 110 DEG C are reacted 16 hours, and rotary evaporation is removed first
The crude product of benzene is purified (R through silica gel chromatographic columnf=0.44, eluent are as follows: n-hexane/ethyl acetate=20:1), rotation is steamed
White crystal A is obtained after out；
(3) by 1,3,5- tribromo-benzene (5.00g, 15.9mmol), Pd (PPh3) 2Cl2 (340mg, 0.490mmol), CuI
(90.0mg, 0.490mmol), PPh3 (129mg, 0.490mmol) are put into three-neck flask, carry out nitrogen protection, and 176mL is added
Triethylamine as solvent, after reaction 15 minute, 9.00mL trimethylsilyl acetylene is added, react 16 hours at 90 DEG C, thick production
Object is purified (R through silica gel chromatographic columnf=0.42, eluent is n-hexane), rotary evaporation obtains faint yellow concentrated solution, cooling
Having crystal to be precipitated is compound 1,3,5- tri- (trimethylsilyl acetylene base) benzene；
(4) by 1,3,5- tri- (trimethylsilyl acetylene base) benzene (1.00g, 2.73mmol) and K2CO3 (57.0mg, 0.410mmol)
It is added in three-necked bottle, carries out nitrogen protection.14.4mL tetrahydrofuran and 4.30mL methanol are added, is stirred at room temperature 6 hours, is passed through
Filter, rotary evaporation remove tetrahydrofuran and methanol solvate, and crude product is purified (R through silica gel chromatographic columnf=0.56, eluent
Are as follows: n-hexane), yellow solid B is obtained after rotary evaporation；
(5) by A(600mg, 1.00mmol), B(94.7mg0.631mmol), Pd (PPh3) 2Cl2(65.1mg,
0.0940mmol), PPh3 (114mg, 0.438 mmol), CuI(68.1mg, 0.371mmol) it is added in three-necked bottle, in nitrogen
Under protection, 50.0mL triethylamine is injected, is reacted 18 hours at 90 DEG C, obtains crude product, then uses methanol, KI aqueous solution, three respectively
Chloromethanes washs crude product, obtains brown solid after drying.
2. according to claim 1 a kind of using l-menthol as the preparation side of the chiral covalent organic framework of chiral source
Method, which is characterized in that the reaction condition in raw material proportioning and step (5) that in the step (2) prepared by monomer A.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111540620A (en) * | 2020-01-08 | 2020-08-14 | 中南民族大学 | Super capacitor with covalent organic framework composite film and preparation method thereof |
| CN111545249A (en) * | 2020-04-27 | 2020-08-18 | 齐齐哈尔大学 | Preparation method of conjugated microporous polymer/palladium-nickel bimetallic catalyst |
| CN111617646A (en) * | 2020-05-11 | 2020-09-04 | 齐齐哈尔大学 | Preparation method of chiral conjugated microporous polymer/silicon dioxide composite membrane |
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| JP2011236143A (en) * | 2010-05-10 | 2011-11-24 | Saitama Univ | Liquid crystalline pyrene derivative, organic semiconductor, and organic semiconductor element |
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| Title |
|---|
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111540620A (en) * | 2020-01-08 | 2020-08-14 | 中南民族大学 | Super capacitor with covalent organic framework composite film and preparation method thereof |
| CN111540620B (en) * | 2020-01-08 | 2022-03-18 | 中南民族大学 | Super capacitor with covalent organic framework composite film and preparation method thereof |
| CN111545249A (en) * | 2020-04-27 | 2020-08-18 | 齐齐哈尔大学 | Preparation method of conjugated microporous polymer/palladium-nickel bimetallic catalyst |
| CN111545249B (en) * | 2020-04-27 | 2023-03-21 | 齐齐哈尔大学 | Preparation method of conjugated microporous polymer/palladium-nickel bimetallic catalyst |
| CN111617646A (en) * | 2020-05-11 | 2020-09-04 | 齐齐哈尔大学 | Preparation method of chiral conjugated microporous polymer/silicon dioxide composite membrane |
| CN111617646B (en) * | 2020-05-11 | 2022-03-04 | 齐齐哈尔大学 | Preparation method of chiral conjugated microporous polymer/silicon dioxide composite membrane |
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