CN109020889A - A kind of pyrazole carboxylic acid copper complex and its preparation method and application - Google Patents
A kind of pyrazole carboxylic acid copper complex and its preparation method and application Download PDFInfo
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- CN109020889A CN109020889A CN201810582794.5A CN201810582794A CN109020889A CN 109020889 A CN109020889 A CN 109020889A CN 201810582794 A CN201810582794 A CN 201810582794A CN 109020889 A CN109020889 A CN 109020889A
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- carboxylic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2217—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
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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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
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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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/10—Complexes comprising metals of Group I (IA or IB) as the central metal
- B01J2531/16—Copper
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Inorganic Chemistry (AREA)
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Abstract
The invention discloses a kind of pyrazole carboxylic acid copper complex, which belongs to anorthic system, P-1 space group, cell parameter are as follows: α=97.058 (4) °, β=92.589 (4) °, γ=107.30 (4) °.Pyrazole carboxylic acid copper complex disclosed by the invention can efficiently activated terminus alkynes, and be catalyzed it and addition reaction carried out to isatin compound, have many advantages, such as preferable catalytic performance, and selectivity is good, reaction condition mildly and high income.And its synthetic method is simple, and product stability is high, utilization easy to spread.
Description
Technical field
The present invention relates to complex materials to synthesize field, and in particular to a kind of pyrazole carboxylic acid copper complex and preparation method thereof
With application.
Background technique
Currently, it is Coordinative Chemistry that purposive design synthesis organic ligand and selection different metal ions, which prepares complex,
The big research hotspot of the one of field.Because complex not only possesses structure abundant, but also combines organic ligand and inorganic metal
The performance of ions has potential application valence in each field such as catalysis, adsorbing separation, ion exchange, optics and biotechnology
Value.Wherein the research using copper complex as catalyst for highly selective, high-conversion rate organic synthesis is always one
A active project.Because this kind of compound not only has superior thermodynamic stability, but also has and a certain number of have
d9The Cu (II) of electron configuration is gathered in a unimolecule, by the synergistic effect and electronics transfer between metal, thus meeting
Generate special reactivity.
Pyrazole carboxylic acid class ligand belongs to one of azaheterocyclic carboxylic acid ligand, is that one kind is matched using relatively widely more organic
Body.Feature of such compound in combination with pyrazole ring rigidity and carboxylic acid compound flexibility, the nitrogen-atoms and oxygen contained
Two donor atoms of atom are even more to enrich coordination mode, and the complex of structure novel can be formed with metallic ion coordination.Again
The presence of nitrogen-atoms identifies base to more hydrogen bonds, can create a special item for the synthesis of supramolecular system
Part can compensate mutually with electronegative carboxyl with electropositive metal cation, to greatly reduce anti-ion
Highly stable electroneutral metal complex can be obtained in effect.
By consulting domestic and international pertinent literature, the copper cooperation generated is reacted with copper acetate and lanthanum chloride with pyrazoles -3- formic acid
Object and as catalyst for being catalyzed terminal alkyne and the technical research of the addition reaction of isatin class compound has not been reported.
Summary of the invention
It is an object of the invention to provide a kind of for being catalyzed the catalyst of the addition reaction of terminal alkyne and isatin class compound.
A kind of pyrazole carboxylic acid copper complex, the pyrazole carboxylic acid copper complex belong to anorthic system, P-1 space group, structure cell ginseng
Number are as follows:α=97.058 (4) °, β=92.589
(4) °, γ=107.30 (4) °；Under its structure expression:
The dissymmetrical structure unit of the pyrazole carboxylic acid copper complex is by a central metal Cu (II), two pyrazoles -3- first
Sour ligand and two waters of coordination composition, central metal Cu (II) respectively on two pyrazoles -3- formic acid two nitrogen-atoms (N1,
N1A oxygen atom (the O3, O3A) coordination) and on two oxygen atoms (O1, O1A) and two waters of coordination, six coordination atoms exist
It is arranged in the form of octahedral around central metal Cu (II), tetra- atoms of O1, O1A, N1, N1A form equatorial plane in ligand,
O3 and O3A then occupies axial position, and Cu-O bond distance's range isCu-N bond distance is
The preparation method of above-mentioned pyrazole carboxylic acid copper complex, comprising the following steps:
Pyrazoles -3- Carboxylic acid ligand is dissolved in n,N-Dimethylformamide solvent, the aqueous solution of copper acetate and lanthanum chloride is added,
It is uniformly mixed, is reacted 2~4 days in 130 DEG C of baking ovens, be cooled to room temperature, obtain mononuclear copper complex.
Further, the molar ratio of the pyrazoles -3- Carboxylic acid ligand and copper acetate and lanthanum chloride is 6:1:1, N, N- diformazan
Base formamide solvent and the volume ratio of distilled water are 1:2.5.
The pyrazole carboxylic acid copper complex can be applied in the addition reaction of catalysis terminal alkyne and isatin class compound
Using.Terminal alkyne is dissolved in n,N-Dimethylformamide solvent, copper complex, mole of terminal alkyne and copper complex is added
Make organic base than tertiary amine for 1:0.02~1:0.001, is added, is eventually adding isatin compound and is uniformly mixed, under room temperature
It is stirred to react 8-24 hours, to which solvent is removed under reduced pressure after reaction, obtains addition product after column chromatographs.Preferably, end
The molar ratio of alkynes and copper complex is 1:0.02~1:0.001, and terminal alkyne is dense in n,N-Dimethylformamide solvent
Degree is 0.1~2.0mol/L, and tertiary amine can be triethylamine, tri-n-butylamine, diisopropyl ethyl amine, mole of terminal alkyne and tertiary amine
Than for 1:1~1:0.05, the molar ratio of isatin compound and terminal alkyne is 1:1~1:2.Preferably, the terminal alkyne,
Its R1Group can be alkyl or benzyl, the isatin compound, R2Group can be halogen (F, Cl, Br, I) or
Alkyl.
It is as follows when reaction:
The utility model has the advantages that pyrazole carboxylic acid copper complex disclosed by the invention can efficiently activated terminus alkynes, and be catalyzed it
Addition reaction is carried out to isatin compound, there is preferable catalytic performance, and selectivity is good, reaction condition is mild and yield
The advantages that high.And its synthetic method is simple, and product stability is high, utilization easy to spread.
Detailed description of the invention
Attached drawing is used to provide further understanding of the present invention, and constitutes part of specification, with reality of the invention
It applies example to be used to explain the present invention together, not be construed as limiting the invention.In the accompanying drawings:
Fig. 1 is that the crystal structure figure of pyrazole carboxylic acid copper complex of the present invention (eliminates carbon atom and water of coordination molecule in figure
On hydrogen atom)；
Fig. 2 is the product hydrogen nuclear magnetic resonance spectrogram of pyrazole carboxylic acid copper complex catalytic addition reaction of the present invention；
Fig. 3 is the product carbon-13 nmr spectra figure of pyrazole carboxylic acid copper complex catalytic addition reaction of the present invention.
Specific embodiment
Hereinafter, preferred embodiments of the present invention will be described with reference to the accompanying drawings, it should be understood that preferred reality described herein
Apply example only for the purpose of illustrating and explaining the present invention and is not intended to limit the present invention.
A kind of embodiment 1: pyrazole carboxylic acid copper complex preparation method with catalytic performance
Pyrazoles -3- Carboxylic acid ligand is dissolved in n,N-Dimethylformamide solvent, the mixing that copper acetate and lanthanum chloride is added is molten
Liquid is uniformly mixed, and is reacted 2 days, is cooled to room temperature in 130 DEG C of baking ovens, and blue blocky copper complex monocrystalline is obtained；(pyrazoles -3- carboxylic acid
The molar ratio of ligand and copper acetate and lanthanum chloride is 6:1:1, and the volume ratio of n,N-Dimethylformamide solvent and distilled water is 1:
2.5)；Yield: 60.7%.
A kind of embodiment 2: pyrazole carboxylic acid copper complex preparation method with catalytic performance
Pyrazoles -3- Carboxylic acid ligand is dissolved in n,N-Dimethylformamide solvent, the mixing that copper acetate and lanthanum chloride is added is molten
Liquid is uniformly mixed, and is reacted 4 days, is cooled to room temperature in 130 DEG C of baking ovens, and blue blocky copper complex monocrystalline is obtained；(pyrazoles -3- carboxylic acid
The molar ratio of ligand and copper acetate and lanthanum chloride is 6:1:1, and the volume ratio of n,N-Dimethylformamide solvent and distilled water is 1:
2.5)；Yield: 69.4%.
Embodiment 3: pyrazole carboxylic acid copper complex is catalyzed addition reaction of the phenylacetylene to N- benzyl isatin:
10mmol phenylacetylene is dissolved in 20mL n,N-Dimethylformamide solvent, 0.2mmol copper complex is added (with copper
Note) it 2.0mmol triethylamine and 10mmol N- benzyl isatin compound is then added is uniformly mixed, which is set
In being stirred to react under room temperature 24 hours, to which solvent is removed under reduced pressure after reaction, addition product M is obtained after column chromatographs
3.18g, yield 94%.The nucleus magnetic hydrogen spectrum data of compound M are as follows: (CDCl3, 300M Hz) and δ=7.59-7.55 (m, 1H),
7.43-7.01(m,12H),6.69-6.65(m,1H),4.84(s,2H),3.78(s,1H)ppm；Compound M carbon-13 nmr spectra
Data are as follows: (CDCl3, 75M Hz) and δ=174.1,142.2,135.0,132.1,130.4,129.0,128.9,128.2,
127.8,127.2,123.8,121.6,109.9,86.6,85.5,69.6,44.1。
Table 1 is the predominant crystal data of Cu complex
aR1=Σ | | Fo|-|Fc||/Σ|Fo|,wR2=[Σ w (Fo 2-Fc 2)2/Σw(Fo 2)2]1/2
Table 2 is the crystal bond distance of Cu manganese complex
| Cu1-N1 | 1.962(3) | Cu1-O1A | 1.997(3) |
| Cu1-N1A | 1.962(3) | Cu1-O3 | 2.532(24) |
| Cu1-O1 | 1.997(3) | Cu1-O3A | 2.532(24) |
Table 3 is the crystal bond angle (°) of Cu complex
| N1-Cu1-N1A | 180.00(2) | O1A-Cu1-O3A | 90.68(96) |
| N1-Cu1-O1 | 81.35(11) | O1-Cu1-O3 | 90.68(96) |
| N1-Cu1-O1A | 98.65(11) | O1A-Cu1-O3A | 90.68(96) |
| N1A-Cu1-O1 | 98.65(11) | O1-Cu1-O3A | 89.32(96) |
| N1A-Cu1-O1A | 81.35(11) | O1A-Cu1-O3 | 89.32(96) |
| O1-Cu1-O1A | 180.00(2) | N1-Cu1-O3 | 86.64(107) |
| N1-Cu1-O3A | 93.36(107) | N1A-Cu1-O3A | 86.64(107) |
| N1A-Cu1-O3 | 93.36(107) | O3-Cu1-O3A | 180.00 |
| O1-Cu1-O3 | 90.68(96) |
Finally, it should be noted that the foregoing is only a preferred embodiment of the present invention, it is not intended to restrict the invention,
Although the present invention is described in detail referring to the foregoing embodiments, for those skilled in the art, still may be used
To modify the technical solutions described in the foregoing embodiments or equivalent replacement of some of the technical features.
All within the spirits and principles of the present invention, any modification, equivalent replacement, improvement and so on should be included in of the invention
Within protection scope.
Claims (6)
1. a kind of pyrazole carboxylic acid copper complex, which is characterized in that the pyrazole carboxylic acid copper complex belongs to anorthic system, the space P-1
Group, cell parameter are as follows: α=97.058 (4) °, β=
92.589 (4) °, γ=107.30 (4) °；Under its structure expression:
2. pyrazole carboxylic acid copper complex as described in claim 1, which is characterized in that its dissymmetrical structure unit is by a center
Ni metal (II), two pyrazoles -3- formic acid ligands and two waters of coordination composition, central metal Cu (II) respectively with two pyrazoles -
On two nitrogen-atoms (N1, N1A) and two oxygen atoms (O1, O1A) and two waters of coordination on 3- formic acid oxygen atom (O3,
O3A) be coordinated, the arrangement in the form of octahedral central metal Cu (II) around of six coordination atoms, O1, O1A in ligand, N1,
Tetra- atoms of N1A form equatorial plane, and O3 and O3A then occupy axial position, and Cu-O bond distance's range is Cu-N bond distance is
3. a kind of preparation method of such as pyrazole carboxylic acid copper complex claimed in claims 1-2, which is characterized in that including following step
It is rapid:
Pyrazoles -3- Carboxylic acid ligand is dissolved in n,N-Dimethylformamide solvent, the aqueous solution of copper acetate and lanthanum chloride, mixing is added
Uniformly, it is reacted 2~4 days in 130 DEG C of baking ovens, is cooled to room temperature, obtains mononuclear copper complex.
4. pyrazole carboxylic acid copper complex preparation method as claimed in claim 3, which is characterized in that the pyrazoles -3- carboxylate ligand
The molar ratio of body and copper acetate and lanthanum chloride is 6:1:1, and the volume ratio of n,N-Dimethylformamide solvent and distilled water is 1:
2.5。
5. the addition of pyrazole carboxylic acid copper complex described in claim 1 applied in catalysis terminal alkyne and isatin class compound
Application in reaction.
6. application as claimed in claim 5, which is characterized in that terminal alkyne is dissolved in n,N-Dimethylformamide solvent, is added
Enter copper complex, the molar ratio of terminal alkyne and copper complex is 1:0.02~1:0.001, and tertiary amine is added and makees organic base, finally
Isatin compound is added to be uniformly mixed, in being stirred to react under room temperature 8-24 hours, to which solvent is removed under reduced pressure after reaction,
Addition product is obtained after column chromatographs.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590671A (en) * | 2019-09-03 | 2019-12-20 | 江苏理工学院 | Copper complex catalyst, preparation method thereof and application thereof in synthesis of 4, 4' -diamino diphenyl sulfone |
| CN111234249A (en) * | 2020-02-17 | 2020-06-05 | 忻州师范学院 | Aliphatic tertiary amine functionalized chromium-based metal organic framework material and preparation method thereof |
| CN111303440A (en) * | 2020-02-17 | 2020-06-19 | 忻州师范学院 | Aliphatic tertiary amine functional zirconium-based metal organic framework material and preparation method thereof |
| CN111518282A (en) * | 2020-06-24 | 2020-08-11 | 江苏理工学院 | Hydroxypyrazole cadmium carboxylate coordination polymer for visible light catalytic degradation of organic dye and preparation and application thereof |
| CN111748101A (en) * | 2020-06-19 | 2020-10-09 | 江苏理工学院 | Hydroxypyrazole manganese carboxylate complex photocatalyst and preparation method and application thereof |
| CN112094236A (en) * | 2020-09-14 | 2020-12-18 | 江苏理工学院 | Indazole zinc dicarboxylate complex with photocatalytic degradation function and preparation method and application thereof |
| CN113045761A (en) * | 2021-02-07 | 2021-06-29 | 南通沃兰化工有限公司 | Pyrazole carboxylic acid manganese coordination polymer photocatalyst and preparation method and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348304A (en) * | 2015-10-18 | 2016-02-24 | 桂林理工大学 | Mononuclear copper pyrazole-3-formic acid complex and preparation method thereof |
| CN105348329A (en) * | 2015-10-18 | 2016-02-24 | 桂林理工大学 | Mononuclear cobalt pyrazole-3-formic acid complex and preparation method thereof |
| CN105906544A (en) * | 2016-04-15 | 2016-08-31 | 上海交通大学 | S-type 3-hydroxy-3-alkynyloxoindole compound and synthetic method and application thereof |
| CN106397321A (en) * | 2016-09-12 | 2017-02-15 | 桂林理工大学 | Pyrazol-3-manganese formate coordination compound and preparation method thereof |
-
2018
- 2018-06-07 CN CN201810582794.5A patent/CN109020889A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105348304A (en) * | 2015-10-18 | 2016-02-24 | 桂林理工大学 | Mononuclear copper pyrazole-3-formic acid complex and preparation method thereof |
| CN105348329A (en) * | 2015-10-18 | 2016-02-24 | 桂林理工大学 | Mononuclear cobalt pyrazole-3-formic acid complex and preparation method thereof |
| CN105906544A (en) * | 2016-04-15 | 2016-08-31 | 上海交通大学 | S-type 3-hydroxy-3-alkynyloxoindole compound and synthetic method and application thereof |
| CN106397321A (en) * | 2016-09-12 | 2017-02-15 | 桂林理工大学 | Pyrazol-3-manganese formate coordination compound and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| MANGILAL CHOUHAN ET AL.: "Catalytic C-H Activation of Arylacetylenes: A Fast Assembly of 3-(Arylethynyl)-3-hydroxyindolin-2-ones Using CuI/DBU", 《SYNTHESIS》 * |
| PAWEŁ CZERWIN´SKI ET AL.: "NHC-Copper(I) Halide-Catalyzed Direct Alkynylation of Trifluoromethyl Ketones on Water", 《CHEM. EUR. J.》 * |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110590671A (en) * | 2019-09-03 | 2019-12-20 | 江苏理工学院 | Copper complex catalyst, preparation method thereof and application thereof in synthesis of 4, 4' -diamino diphenyl sulfone |
| CN110590671B (en) * | 2019-09-03 | 2022-12-23 | 江苏理工学院 | Copper complex catalyst, preparation method thereof and application thereof in synthesis of 4,4' -diamino diphenyl sulfone |
| CN111234249A (en) * | 2020-02-17 | 2020-06-05 | 忻州师范学院 | Aliphatic tertiary amine functionalized chromium-based metal organic framework material and preparation method thereof |
| CN111303440A (en) * | 2020-02-17 | 2020-06-19 | 忻州师范学院 | Aliphatic tertiary amine functional zirconium-based metal organic framework material and preparation method thereof |
| CN111234249B (en) * | 2020-02-17 | 2021-11-19 | 忻州师范学院 | Aliphatic tertiary amine functionalized chromium-based metal organic framework material and preparation method thereof |
| CN111303440B (en) * | 2020-02-17 | 2021-11-19 | 忻州师范学院 | Aliphatic tertiary amine functional zirconium-based metal organic framework material and preparation method thereof |
| CN111748101A (en) * | 2020-06-19 | 2020-10-09 | 江苏理工学院 | Hydroxypyrazole manganese carboxylate complex photocatalyst and preparation method and application thereof |
| CN111518282A (en) * | 2020-06-24 | 2020-08-11 | 江苏理工学院 | Hydroxypyrazole cadmium carboxylate coordination polymer for visible light catalytic degradation of organic dye and preparation and application thereof |
| CN111518282B (en) * | 2020-06-24 | 2022-03-04 | 江苏理工学院 | Hydroxypyrazole cadmium carboxylate coordination polymer for visible light catalytic degradation of organic dye and preparation and application thereof |
| CN112094236A (en) * | 2020-09-14 | 2020-12-18 | 江苏理工学院 | Indazole zinc dicarboxylate complex with photocatalytic degradation function and preparation method and application thereof |
| CN113045761A (en) * | 2021-02-07 | 2021-06-29 | 南通沃兰化工有限公司 | Pyrazole carboxylic acid manganese coordination polymer photocatalyst and preparation method and application thereof |
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