CN108409976A - The topological organic polymer of solubility based on full conjugate rigid structure and quasi- phthalocyanine activated centre and preparation - Google Patents
The topological organic polymer of solubility based on full conjugate rigid structure and quasi- phthalocyanine activated centre and preparation Download PDFInfo
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- CN108409976A CN108409976A CN201810051617.4A CN201810051617A CN108409976A CN 108409976 A CN108409976 A CN 108409976A CN 201810051617 A CN201810051617 A CN 201810051617A CN 108409976 A CN108409976 A CN 108409976A
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- 229920000620 organic polymer Polymers 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 8
- 239000010941 cobalt Substances 0.000 claims abstract description 8
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052742 iron Inorganic materials 0.000 claims abstract description 7
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims abstract description 7
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 7
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 7
- 239000011701 zinc Substances 0.000 claims abstract description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910018957 MClx Inorganic materials 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 229910001510 metal chloride Inorganic materials 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- 230000021615 conjugation Effects 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 13
- 239000002861 polymer material Substances 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 4
- 239000002184 metal Substances 0.000 abstract description 4
- 150000002739 metals Chemical class 0.000 abstract description 2
- 238000004458 analytical method Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000001237 Raman spectrum Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000003487 electrochemical reaction Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000006479 redox reaction Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000004088 simulation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 241001269238 Data Species 0.000 description 1
- JZLFOBXOHCGSBP-YOXFSPIKSA-N N#C[C@H](C(C=C1C#N)C#N)C=C1C#N Chemical compound N#C[C@H](C(C=C1C#N)C#N)C=C1C#N JZLFOBXOHCGSBP-YOXFSPIKSA-N 0.000 description 1
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 238000000026 X-ray photoelectron spectrum Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010130 dispersion processing Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000004146 energy storage Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Catalysts (AREA)
Abstract
The topological organic polymer of solubility based on full conjugate rigid structure and quasi- phthalocyanine activated centre and preparation, belong to the polymer material technical field of topological structure.The present invention is prepared for rigidity, the topological organic polymer (TOP) of the solubility of full conjugate structure, while introducing in structure that one or more metals are monatomic to be used as active sites, obtains the new catalysts materials to serve many purposes.
Description
Technical field
The present invention relates to a kind of topological organic polymers of the solubility based on full conjugate rigid structure and quasi- phthalocyanine activated centre
Object (TOP) and preparation method thereof, belongs to the polymer material of topological structure.
Technical background
Two dimension, multidimensional polymer material with topological structure, it is covalently organic such as metal organic frame polymer (MOF)
Framework polymer (COF) and covalent organic polymer (COP) etc. there are contained element species to enrich, structure-controllable and stability
The features such as excellent, is widely used in the research in the fields such as gas absorption, catalysis, semi-conducting material, has obtained whole world research
The attention of personnel.However the insoluble application and development for limiting them naturally caused by intrinsic crosslinking frame structure.Phase
Than under, soluble material or the material that can carry out liquid phase processing have prodigious answer in fields such as energy storage, semi-conducting materials
With value.So far, there are some technologies for developing favorable dispersibility or covalently having for dispersion processing processing can be carried out
Machine frame polymer material.It is such as synthesized by lotion, forms the nano particle with certain dispersibility；By being grafted alkane in branch
The hydrophilic side group such as base chain and sulfonate radical promotes dissolubility etc..However, for nano-particle, it is long-term to maintain stable dispersion
System is still highly difficult.And be difficult to dissolve since cross-linked polymer can be swollen, the method for graft modification is to solubility
Promotion it is limited, and original performance can be affected.According to the inventors knowledge, full conjugate rigid structure and quasi- phthalocyanine activated centre
The topological organic polymer (TOP) of solubility belong to the novel polymer material with topological structure, not by exploitation preparation.
Invention content：
It is an object of the invention to propose a kind of solubility of completely new full conjugate rigid structure and quasi- phthalocyanine activated centre
Topological organic polymer (TOP) material and preparation method thereof.
The topological organic polymer of solubility based on full conjugate rigid structure and quasi- phthalocyanine activated centre, which is characterized in that
It is conjugated rigid structure polymer for a kind of two dimension, general structure (1) is as follows：Two dotted lines wherein on phenyl ring represent omission
Connection is strong.
Wherein M is one or two and two or more metallic atoms in iron, cobalt, nickel, manganese, zinc.
The preparation method of above compound, by 1,2,4,5- benzene, four formonitrile HCN as structure synthon, metal chloride
MClx(M is iron, cobalt, nickel, manganese, zinc) is activated centre, with 1,8- diazabicylos, 11 carbon -7- alkene (DBU) be catalyst into
Row polymerisation obtains compound (I), includes the following steps：
Take four formonitrile HCN of monomer 1,2,4,5- benzene and metal chloride MClxBe dissolved in solvent, M be selected from iron, cobalt, nickel, manganese,
Zinc, X is identical as the chemical valence of M, addition catalyst 1, after 11 carbon -7- alkene (DBU) of 8- diazabicylos, is uniformly mixed；Heating
It to 70 DEG C -220 DEG C, is reacted, reacts postcooling, washing separation.
The one kind of solvent in ethylene glycol, DMAC N,N' dimethyl acetamide, N,N-dimethylformamide, dimethyl sulfoxide (DMSO) etc.
Or it is several.Four formonitrile HCN of 1,2,4,5- benzene and metal chloride MClxDosage relation there is no limit.
The topological organic polymer of the solubility based on full conjugate rigid structure and quasi- phthalocyanine activated centre of the present invention has two
Kind crystal structure types, orthorhombic system and hexagonal crystal system.
The topological organic polymer of solubility of the gained of the invention based on full conjugate rigid structure and quasi- phthalocyanine activated centre is molten
Solution, such as ethylene glycol, n,N-dimethylacetamide, n,N-Dimethylformamide, dimethyl sulfoxide (DMSO) are formed in polar solvent.
The present invention is prepared for rigidity, the topological organic polymer (TOP) of the solubility of full conjugate structure, while drawing in structure
It is monatomic as active sites to have entered one or more metals, has obtained the new catalysts materials with potential multiple use, such as
Catalytic performance (such as catalytic electrochemical reaction redox reactions), gas or adsorption of metal ions.
Description of the drawings
Fig. 1 is the TOP material solid nuclear-magnetisms that embodiment 1 obtains13C spectrum analysis figures；
Fig. 2 is the TOP material Raman spectrums that embodiment 1 obtains；
Fig. 3 is the TOP material transmission electron microscopic datas that embodiment 1 obtains；
Wherein a is common transmission electron microscope data, and b is high-resolution-ration transmission electric-lens data, and c, d are high power details in a play not acted out on stage, but told through dialogues spherical aberration Electronic Speculum number
According to bright spot is monoatomic metal in figure.
Fig. 4 is the TOP material crystal structure simulation drawings that embodiment 1 obtains.
Fig. 5 is the different solutions that the TOP materials that embodiment 1 obtains are formed in different solvents；
Fig. 6 is the Raman spectrum for the TOP materials that embodiment 2 obtains.
Fig. 7 is the XPS spectrum analysis for the TOP materials that embodiment 2 obtains.
Fig. 8 is application of the embodiment 1 on oxygen reduction catalyst.
The present invention will be further described with reference to embodiment for specific implementation mode, but the present invention and is limited to following implementation
Example.
Embodiment 1
The synthesis of topological organic polymer (TOP)
Take four formonitrile HCN of monomer 1,2,4,5- benzene and excessive metal chloride MClx(M is iron, cobalt, nickel, manganese, zinc) is dissolved in molten
In agent, it is added the catalyst 1 of overall solution volume catalyst 1%~5%, after 11 carbon -7- alkene (DBU) of 8- diazabicylos, mixes
It closes uniform.After being warming up to 70 DEG C of reactions 15 minutes, 180~220 DEG C are warming up to, is stirred to react 1~4 hour (using directly heating
Or the forms such as other electrical heating, using other mode of heatings, heating power is 70~220W).Gradually it is down to room temperature, solution face
Discoloration is deep to blackish green or black, stops reaction, and blackish green product is obtained after being spin-dried for solvent, is centrifuged after washing and obtains final product TOP,
Yield is 70%.Solid13C NMR：168.7ppm, 137.2ppm, 117.9ppm, 63.9ppm are shown in Fig. 1.Raman spectrum analysis is shown in
Fig. 2, analysis are shown in Table 1.Gained TOP products have uniform monatomic distribution, two-dimensional layered structure, see Fig. 3.Gained TOP products have
There are rigid crystals structure, structural simulation to see Fig. 4.
Table 1, TOP material Raman spectrum analyses.
Dissolubility：
The blackish green TOP of gained is dissolvable in water in polar solvent, such as ethylene glycol solution, n,N-dimethylacetamide solution, N,
Dinethylformamide solution, dimethyl sulphoxide solution, TOP solution are shown in Fig. 5.
Embodiment 2
The synthesis of topological organic polymer (TOP)
Take four formonitrile HCN of monomer 1,2,4,5- benzene and excessive metal chloride MClx(M is cobalt) is dissolved in solvent, is added molten
The catalyst 1 of liquid total volume catalyst 1%~5% after 11 carbon -7- alkene (DBU) of 8- diazabicylos, is uniformly mixed.Heating
After being reacted 15 minutes to 75 DEG C, 220 DEG C are warming up to, is stirred to react 1~4 hour.It is gradually down to room temperature, solution colour change is deep to ink
Green or black stop reaction, and blackish green product is obtained after being spin-dried for solvent, are centrifuged after washing and obtain final product TOP, yield is
70%.Raman spectrum analysis is shown in Fig. 6.XPS analysis is shown in Fig. 7.
Table 2, TOP material Raman spectrum analyses.
Catalyst Ia
Blackish green powder.Be dissolved in 0.1M potassium hydroxide solutions, using carbon paper as working electrode, platinum filament be to electrode,
Ag/AgCl is reference electrode, is passed through oxygen and is extremely saturated, can catalytic electrochemical reaction redox reactions (ORR).Take-off potential
903mV, half wave potential 834mV.See Fig. 8.
Claims (5)
1. the topological organic polymer of solubility based on full conjugate rigid structure and quasi- phthalocyanine activated centre, which is characterized in that be
A kind of two dimension conjugation rigid structure polymer, general structure (1) are as follows：Two dotted lines wherein on phenyl ring represent the company omitted
It connects strong；
Wherein M is one or two and two or more metallic atoms in iron, cobalt, nickel, manganese, zinc.
2. a kind of preparation method of the topological organic polymer of solubility based on full conjugate rigid structure and quasi- phthalocyanine activated centre,
It is characterized by comprising the following steps：Take four formonitrile HCN of monomer 1,2,4,5- benzene and metal chloride MClxIt is dissolved in solvent, M
Selected from iron, cobalt, nickel, manganese, zinc, X is identical as the chemical valence of M, and catalyst 1,11 carbon -7- alkene (DBU) of 8- diazabicylos is added
Afterwards, it is uniformly mixed；Heating is reacted, and postcooling, washing separation are reacted.
3. according to the method for claim 2, which is characterized in that solvent is selected from ethylene glycol, n,N-dimethylacetamide, N, N- diformazans
One or more of base formamide, dimethyl sulfoxide (DMSO) etc..
4. according to the method for claim 2, which is characterized in that the temperature for heating reaction is 70 DEG C -220 DEG C.
5. the topological organic polymer of the solubility described in claim 1 based on full conjugate rigid structure and quasi- phthalocyanine activated centre
Application, be dissolved in polar solvent and form solution.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112111132A (en) * | 2020-09-24 | 2020-12-22 | 中国科学院长春光学精密机械与物理研究所 | Conjugated microporous poly phthalocyanine-graphene composite laser protection material and preparation method thereof |
| CN112159518A (en) * | 2020-09-24 | 2021-01-01 | 中国科学院长春光学精密机械与物理研究所 | Poly-phthalocyanine light amplitude limiting material with conjugated micropore structure and preparation method thereof |
| CN112979975A (en) * | 2021-02-02 | 2021-06-18 | 上海交通大学烟台信息技术研究院 | Preparation method of covalent organic framework material containing two metal ions |
| CN113363628A (en) * | 2021-06-03 | 2021-09-07 | 中南大学 | Electrolyte for aluminum air battery and preparation method thereof |
| CN113769781A (en) * | 2020-06-10 | 2021-12-10 | 北京化工大学 | Covalent organic framework-containing polymer material catalyst, preparation method and application thereof, and method for catalytic oxidation of alkane |
| CN115417997A (en) * | 2021-05-12 | 2022-12-02 | 北京化工大学 | Soluble covalent organic framework polymer material, application thereof and supergravity method macroscopic preparation method |
| CN116731294A (en) * | 2022-08-17 | 2023-09-12 | 四川大学 | Conjugated polymer biocatalysis material and preparation method and application thereof |
| CN117299212A (en) * | 2023-09-04 | 2023-12-29 | 东北师范大学 | Cobalt phthalocyanine covalent organic framework desulfurization catalyst and preparation method and application thereof |
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| CN113769781A (en) * | 2020-06-10 | 2021-12-10 | 北京化工大学 | Covalent organic framework-containing polymer material catalyst, preparation method and application thereof, and method for catalytic oxidation of alkane |
| CN113769781B (en) * | 2020-06-10 | 2024-07-19 | 北京化工大学 | Catalyst containing covalent organic framework polymer material, preparation method and application thereof, and method for catalytic oxidation of alkane |
| CN112111132A (en) * | 2020-09-24 | 2020-12-22 | 中国科学院长春光学精密机械与物理研究所 | Conjugated microporous poly phthalocyanine-graphene composite laser protection material and preparation method thereof |
| CN112159518A (en) * | 2020-09-24 | 2021-01-01 | 中国科学院长春光学精密机械与物理研究所 | Poly-phthalocyanine light amplitude limiting material with conjugated micropore structure and preparation method thereof |
| CN112111132B (en) * | 2020-09-24 | 2021-10-08 | 中国科学院长春光学精密机械与物理研究所 | Conjugated microporous poly phthalocyanine-graphene composite laser protection material and preparation method thereof |
| CN112979975A (en) * | 2021-02-02 | 2021-06-18 | 上海交通大学烟台信息技术研究院 | Preparation method of covalent organic framework material containing two metal ions |
| CN115417997A (en) * | 2021-05-12 | 2022-12-02 | 北京化工大学 | Soluble covalent organic framework polymer material, application thereof and supergravity method macroscopic preparation method |
| CN113363628A (en) * | 2021-06-03 | 2021-09-07 | 中南大学 | Electrolyte for aluminum air battery and preparation method thereof |
| CN113363628B (en) * | 2021-06-03 | 2022-06-24 | 中南大学 | Electrolyte for aluminum-air battery and preparation method thereof |
| CN116731294A (en) * | 2022-08-17 | 2023-09-12 | 四川大学 | Conjugated polymer biocatalysis material and preparation method and application thereof |
| CN117299212A (en) * | 2023-09-04 | 2023-12-29 | 东北师范大学 | Cobalt phthalocyanine covalent organic framework desulfurization catalyst and preparation method and application thereof |
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