CN110041455B - Alkyne polymerization method - Google Patents
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- CN110041455B CN110041455B CN201910421904.4A CN201910421904A CN110041455B CN 110041455 B CN110041455 B CN 110041455B CN 201910421904 A CN201910421904 A CN 201910421904A CN 110041455 B CN110041455 B CN 110041455B
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- 238000006116 polymerization reaction Methods 0.000 title claims abstract description 24
- 150000001345 alkine derivatives Chemical class 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 10
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000178 monomer Substances 0.000 claims abstract description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 8
- LFZJRTMTKGYJRS-UHFFFAOYSA-N 1-chloro-4-ethynylbenzene Chemical group ClC1=CC=C(C#C)C=C1 LFZJRTMTKGYJRS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052751 metal Inorganic materials 0.000 claims abstract description 5
- 239000002184 metal Substances 0.000 claims abstract description 5
- 229920006158 high molecular weight polymer Polymers 0.000 claims abstract description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 229910052786 argon Inorganic materials 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 239000002685 polymerization catalyst Substances 0.000 claims description 3
- 238000001953 recrystallisation Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000010926 purge Methods 0.000 claims 1
- 239000002861 polymer material Substances 0.000 abstract description 2
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 229920000909 polytetrahydrofuran Polymers 0.000 abstract 1
- 230000009257 reactivity Effects 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 10
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- WYURNTSHIVDZCO-SVYQBANQSA-N deuterated tetrahydrofuran Substances [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 229910052723 transition metal Inorganic materials 0.000 description 5
- 150000003624 transition metals Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- GRBJPHPMYOUMJV-UHFFFAOYSA-N 1-chloro-3-ethynylbenzene Chemical group ClC1=CC=CC(C#C)=C1 GRBJPHPMYOUMJV-UHFFFAOYSA-N 0.000 description 1
- YFPQIXUNBPQKQR-UHFFFAOYSA-N 1-ethynyl-2-fluorobenzene Chemical group FC1=CC=CC=C1C#C YFPQIXUNBPQKQR-UHFFFAOYSA-N 0.000 description 1
- PTRUTZFCVFUTMW-UHFFFAOYSA-N 1-ethynyl-3-fluorobenzene Chemical group FC1=CC=CC(C#C)=C1 PTRUTZFCVFUTMW-UHFFFAOYSA-N 0.000 description 1
- ZASXCTCNZKFDTP-UHFFFAOYSA-N 1-ethynyl-3-methoxybenzene Chemical group COC1=CC=CC(C#C)=C1 ZASXCTCNZKFDTP-UHFFFAOYSA-N 0.000 description 1
- QXSWHQGIEKUBAS-UHFFFAOYSA-N 1-ethynyl-4-fluorobenzene Chemical group FC1=CC=C(C#C)C=C1 QXSWHQGIEKUBAS-UHFFFAOYSA-N 0.000 description 1
- KBIAVTUACPKPFJ-UHFFFAOYSA-N 1-ethynyl-4-methoxybenzene Chemical group COC1=CC=C(C#C)C=C1 KBIAVTUACPKPFJ-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 150000000475 acetylene derivatives Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- -1 transition metal iridium complexes Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F38/00—Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/72—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44
- C08F4/80—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from metals not provided for in group C08F4/44 selected from iron group metals or platinum group metals
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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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
Abstract
The invention relates to an alkyne polymerization method, belonging to the technical field of high polymer materials. Catalyzing alkyne to carry out polymerization reaction in the presence of a catalyst, wherein the catalyst is a metal iridium complex [ Ir (dncot) ((MeCN))2]SbF6. Although the catalyst has been reported in the literature, the invention provides the application of the catalyst in catalyzing alkyne polymerization for the first time, and the catalyst can realize complete conversion of 4-chloro-phenylacetylene monomer and obtain high-molecular-weight polymer with high yield (yield is 100%, and Mn is 50300). The disadvantage of this catalytic system is that it can also catalyze the polymerization of tetrahydrofuran, but the reactivity is not high and the polytetrahydrofuran impurities can be purified away by means of an extractor.
Description
Technical Field
The invention relates to an alkyne polymerization catalyst which is a transition metal iridium complex. The invention provides application of the catalyst in catalyzing alkyne polymerization for the first time, and belongs to the technical field of high polymer materials.
Background
The transition metal catalyzed polymerization of substituted acetylene is an effective method for synthesizing substituted polyacetylene, and has potential application prospect in the fields of organic light-emitting diodes, gas separation membranes, stimulus response materials and the like. The transition metals rhodium, molybdenum, tungsten, nickel, palladium and iron are common high-efficiency catalysts for catalyzing the polymerization of substituted phenylacetylene. In recent years, although studies on the polymerization of phenylacetylene catalyzed by transition metal iridium complexes have been reported, the iridium catalysts used have low activity, low monomer conversion rate and low polymerization degree.
The invention synthesizes diene ligand containing aryl conjugated structure for polymerization reaction of substituted alkyne catalyzed by iridium, and improves activity and selectivity of catalyst by electronic effect and steric hindrance on ligand, thereby improving yield and selectivity of substituted phenylacetylene polymerization reaction.
Disclosure of Invention
The technical problem solved by the invention is as follows: the invention relates to an alkyne polymerization method, and a catalyst is a transition metal iridium complex. Although the catalyst has been reported in the literature, the invention provides the application of the catalyst in catalyzing alkyne polymerization for the first time, and the catalyst can realize complete conversion of 4-chloro-phenylacetylene monomer and obtain high-molecular-weight polymer with high yield (yield is 100 percent, and Mn is 50300).
In order to solve the technical problems, the technical scheme of the invention is as follows: the alkyne polymerizing process is one alkyne polymerizing reaction catalyzed in organic solvent and in the presence of catalyst to realize the complete conversion of the monomer to obtain high yield high molecular weight polymer yield-100% and Mn-50300; the organic solvent is tetrahydrofuran, and the catalyst is metal iridium complex [ Ir (dncot) ((MeCN))2]SbF6The alkyne is 4-chloro-phenylacetylene 2f, the polymerization temperature is 25 ℃ at room temperature, the polymerization time is 5h, the amount of the polymerization catalyst is 1% of the amount of the polymerized monomer substance, and the catalyst has the following structure:
preferably, the metal iridium complex [ Ir (dcnot) (MeCN)2]SbF6The preparation method comprises the following steps: to a 25mL Schlenk reaction tube was added [ Ir (dncot) Cl]2(100.00mg, 0.09mmol) and purged under argon for 15 minutes, then 3mL of dichloromethane and 3mL of acetonitrile were sequentially added to the reaction tube under argon, and finally AgSbF was added under argon6(65.30mg, 0.19mmol) was weighed into a reaction tube. After the reaction was stirred for a further 1.5h, it was filtered off, dried by spinning and isolated by recrystallization from acetonitrile and diethyl ether to yield 147.00mg (96%) of the yellow product.
Detailed Description
Example 1 Synthesis of catalyst 1a
To a 25mL Schlenk reaction tube was added [ Ir (dncot) Cl]2(100.00mg, 0.09mmol) and purged under argon for 15 minutes, then 3mL of dichloromethane and 3mL of acetonitrile were sequentially added to the reaction tube under argon, and finally AgSbF was added under argon6(65.30mg, 0.19mmol) was weighed into a reaction tube. After the reaction was stirred for a further 1.5h, it was filtered off, dried by spinning and isolated by recrystallization from acetonitrile and diethyl ether to yield 147.00mg (96%) of the yellow product. Mp:263-264 ℃.1H NMR(400MHz；(CD3CN):δ7.67-7.65(m,4H),7.51(s,4H),7.35-7.33(m,4H),5.48(s,4H).13C NMR(400MHz；(CD3)2SO):δ143.6,131.9,127.4,126.0,124.8,118.5,61.3，1.5.HRMS(m/z)calculated(C28H22IrN2Na):602.1304 Found:602.1319.
Example 2 application of catalyst to catalysis of polymerization of phenylacetylene and ring-substituted derivatives thereof
Adding a certain amount of iridium catalyst into a 25mL clean Schlenk reaction tube, vacuumizing for 15 minutes under argon atmosphere, adding a certain amount of tetrahydrofuran solution under argon atmosphere, carrying out freeze degassing for 45 minutes in liquid nitrogen, returning to room temperature, adding 1 equivalent of treated polymeric monomer under argon atmosphere, initiating the polymerization reaction of the monomers at a certain temperature, adding a certain amount of nitromethane or benzyl ether as an internal standard after reacting for 5 hours, taking a proper amount of reaction liquid from the reaction system for nuclear magnetic monitoring, and finally adding a large amount of methanol into the reaction system to quench the reaction. Centrifuging, separating, drying under vacuum to constant weight, weighing and calculating the separation yield.
The results of the experiments obtained are given in the following table (number average molecular weight M of the polymer)nAnd molecular weight polydispersity index PDI determined using marwen Viscotek 270Max multi-detector gel permeation chromatograph):
the alkyne is phenylacetylene 2a, 2-fluorophenylacetylene 2b, 3-fluorophenylacetylene 2c, 4-fluorophenylacetylene 2d, 3-chlorophenylacetylene 2e, 4-chlorophenylacetylene 2f, 3-methoxyphenylacetylene 2g and 4-methoxyphenylacetylene 2h
Yellow solid.1H NMR(400MHz；CDCl3):δ6.97-6.93(m,3H),6.63(d,J＝6.4Hz,2H),5.85(s,1H).13C NMR(400MHz；CDCl3):δ143.0,139.4,132.0,127.9,127.7,126.9.
Yellow solid.1H NMR(400MHz；d8-THF):δ6.97-6.95(m,1H),6.73-6.69(m,2H),6.49-6.46(m,1H),5.81(s,1H).13C NMR(400MHz；d8-THF):δ161.6,159.2,134.8,133.9,131.4,129.4,124.4,115.8.
Brick red solid.1H NMR(400MHz；d8-THF):δ7.02-6.96(m,1H),6.81-6.77(m,1H),6.55-6.51(m,2H),5.89(s,1H).13C NMR(400MHz；d8-THF):δ165.0,162.5,145.5,139.9,132.9,130.4,124.3,114.9.
Yellow solid.1H NMR(400MHz；CDCl3):δ6.72-6.62(m,4H),5.72(s,1H).13C NMR(400MHz；CDCl3):δ164.4,161.9,139.8,132.2,130.1,115.7.
Yellow solid.1H NMR(400MHz；d8-THF):δ7.11(d,J＝8.0Hz,1H),6.98(t,J＝8.0Hz,1H),6.79(s,1H),6.63(d,J＝7.6Hz,1H),5.88(s,1H).13C NMR(400MHz；d8-THF):δ161.6,159.2,134.8,133.9,131.4,129.4,124.4,115.8.
Yellow solid.1H NMR(400MHz；d8-THF):δ7.03(d,J＝8.4Hz,2H),6.69(d,J＝8.4Hz,2H),5.84(s,1H).13C NMR(400MHz；d8-THF):δ141.7,139.6,134.2,132.4,129.8,129.1.
Yellow solid.1H NMR(400MHz；CDCl3):δ6.82(t,J＝8.0Hz,1H),6.53(d,J＝8.0Hz,1H),6.27(t,J＝7.6Hz,2H),5.85(s,1H),3.54(s,3H).13C NMR(400MHz；CDCl3):δ160.6,145.3,140.3,132.6,129.4,121.4,113.5,113.3,55.3.
A dark green solid.1H NMR(400MHz；CDCl3):δ6.62(d,J＝8.0Hz，2H),6.46(d,J＝8.4Hz,2H),5.76(s,1H),3.58(s,3H).13C NMR(400MHz；CDCl3):δ158.7,138.8,135.9,130.4,128.9,113.2,55.3.
Claims (2)
1. A method of polymerizing alkynes, characterized by: the alkyne is catalyzed to carry out polymerization reaction in an organic solvent in the presence of a catalyst, the complete conversion of the polymerization monomer can be realized, high-yield high-molecular-weight polymer yield is 100 percent, and Mn 50300 is obtained, the organic solvent is tetrahydrofuran, and the catalyst is a metal iridium complex [ Ir (dncot) ((MeCN))2]SbF6The alkyne is 4-chloro phenylacetylene, the polymerization temperature is 25 ℃ at room temperature, the polymerization time is 5h, the amount of the polymerization catalyst is 1% of the amount of the polymerization monomer substance, and the catalyst has the following structure:
2. the method of polymerizing alkynes according to claim 1, characterized in that: the metal iridium complex [ Ir (dncot) ((MeCN))2]SbF6The preparation method comprises the following steps: to a 25mL Schlenk reaction tube was added [ Ir (dncot) Cl]2100.00mg, 0.09mmol, and purging under argon for 15 minutes, then 3mL of dichloromethane and 3mL of acetonitrile were sequentially added to the reaction tube under argon, and finally AgSbF was added under argon665.30mg, 0.19mmol were weighed into the reaction tube, and after the reaction was stirred for 1.5h, it was filtered, spun dry and isolated by recrystallization from acetonitrile and ether to yield 147.00mg 96% of a yellow product.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997034857A1 (en) * | 1996-03-20 | 1997-09-25 | Nexstar Pharmaceuticals, Inc. | Method for the cyclotrimerization of alkynes in aqueous solutions |
| CN109336887A (en) * | 2018-09-07 | 2019-02-15 | 中山大学 | A kind of benzimidazole and chiral heterocycle class compound and its preparation method and application |
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2019
- 2019-05-21 CN CN201910421904.4A patent/CN110041455B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997034857A1 (en) * | 1996-03-20 | 1997-09-25 | Nexstar Pharmaceuticals, Inc. | Method for the cyclotrimerization of alkynes in aqueous solutions |
| CN109336887A (en) * | 2018-09-07 | 2019-02-15 | 中山大学 | A kind of benzimidazole and chiral heterocycle class compound and its preparation method and application |
Non-Patent Citations (1)
| Title |
|---|
| Rhodium Dinaphthocyclooctatetraene Complexes: Synthesis, Characterization and Catalytic Activity in [5+2] Cycloadditions;Wender, P.A.等;《ANGEWANDTE CHEMIE-INTERNATIONAL EDITION》;20121231;第2736-2740页 * |
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