CN102329210A - 2, 6-di(aryl)-anthraquinone and preparation method thereof - Google Patents
2, 6-di(aryl)-anthraquinone and preparation method thereof Download PDFInfo
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- anthraquinone
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- 125000003118 aryl group Chemical group 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims abstract description 12
- 238000010521 absorption reaction Methods 0.000 claims abstract description 11
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 7
- 238000007341 Heck reaction Methods 0.000 claims abstract description 4
- JUFYHUWBLXKCJM-UHFFFAOYSA-N 2,6-dibromoanthracene-9,10-dione Chemical class BrC1=CC=C2C(=O)C3=CC(Br)=CC=C3C(=O)C2=C1 JUFYHUWBLXKCJM-UHFFFAOYSA-N 0.000 claims abstract 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims abstract 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- -1 4-aminostyryl Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 8
- 150000004056 anthraquinones Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 3
- IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-UHFFFAOYSA-N 0.000 claims description 3
- YFZHODLXYNDBSM-UHFFFAOYSA-N 1-ethenyl-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(C=C)C=C1 YFZHODLXYNDBSM-UHFFFAOYSA-N 0.000 claims description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 2
- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 claims description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N para-hydroxystyrene Natural products OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims description 2
- IGDLZDCWMRPMGL-UHFFFAOYSA-N 2-ethenylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C=C)C(=O)C2=C1 IGDLZDCWMRPMGL-UHFFFAOYSA-N 0.000 claims 1
- KFDVPJUYSDEJTH-UHFFFAOYSA-N 4-ethenylpyridine Chemical compound C=CC1=CC=NC=C1 KFDVPJUYSDEJTH-UHFFFAOYSA-N 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 230000021615 conjugation Effects 0.000 abstract description 6
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
- CXTPIHZYOGDSLV-UHFFFAOYSA-N 1-bromoanthracene-9,10-dione Chemical class O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Br CXTPIHZYOGDSLV-UHFFFAOYSA-N 0.000 description 12
- 229910052763 palladium Inorganic materials 0.000 description 12
- 229910052698 phosphorus Inorganic materials 0.000 description 12
- 239000011574 phosphorus Substances 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- 238000004821 distillation Methods 0.000 description 11
- 230000001681 protective effect Effects 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000010438 heat treatment Methods 0.000 description 10
- WGGLDBIZIQMEGH-UHFFFAOYSA-N 1-bromo-4-ethenylbenzene Chemical compound BrC1=CC=C(C=C)C=C1 WGGLDBIZIQMEGH-UHFFFAOYSA-N 0.000 description 4
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 4
- JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960001701 chloroform Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- IYRHBDVSMINOTQ-UHFFFAOYSA-N aniline;ethene Chemical compound C=C.NC1=CC=CC=C1 IYRHBDVSMINOTQ-UHFFFAOYSA-N 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229920001746 electroactive polymer Polymers 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000006303 photolysis reaction Methods 0.000 description 1
- 230000015843 photosynthesis, light reaction Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Abstract
一种2，6-二(芳香基)-蒽醌及其制备方法，是将电子给体或电子受体基团在2，6位连接在蒽醌环两侧，将2，6-二溴蒽醌类衍生物和含有乙烯基的取代基团在醋酸钯和三-O-甲氧基磷的催化作用下，在碱性条件下发生赫克(Heck Reaction)反应生成的，其分子结构通式如下：其中：R为乙烯基的取代基团，电子给体基团或电子受体基团。由于该化合物具有较大的共轭平面，同时该化合物具有较好的光化学稳定性、热稳定性和溶解性，因此能较好的捕获多光子能力并激发产生多光子吸收和非线性吸收现象，从而能满足光电转换材料和非线性吸收材料等多方面的应用要求。A kind of 2,6-bis(aryl)-anthraquinone and its preparation method is that the electron donor or electron acceptor group is connected on both sides of the anthraquinone ring at the 2,6 position, and the 2,6-dibromo Anthraquinone derivatives and vinyl-containing substituent groups are catalyzed by palladium acetate and tri-O-methoxyphosphorus, and are produced by a Heck reaction under alkaline conditions. The formula is as follows:
Wherein: R is a vinyl substituent group, an electron donor group or an electron acceptor group. Because the compound has a large conjugation plane, and the compound has good photochemical stability, thermal stability and solubility, it can better capture multi-photon and stimulate multi-photon absorption and nonlinear absorption. Therefore, it can meet various application requirements such as photoelectric conversion materials and nonlinear absorption materials.
Description
Technical field
The present invention relates to one type of symmetric form anthraquinone derivatives, particularly a kind of 2,6-two (aromatic base)-anthraquinone and preparation method thereof can satisfy many-sided application requiring such as photoelectric conversion material and non-linear absorption material.
Background technology
In recent years, because the huge applications of organic multiphoton absorption material aspect photonics and biologic pharmacological science, the novel organic molecule that makes many scientists design for it to have big molecular conjugation system.As far back as 1931,
What Mayer had foretold this non-linear phenomena in theory exists that { document sees reference: [1] P.N.Prasad; D.R.Ulrich, Nonlinear Optical and Electroactive Polymers [M] .NewYork, Plenum; 1988.}; And along with science and technology development, the phenomenon of multiphoton absorption is also come to light one by one in experimentation by scientists and confirms { document that sees reference [2]: W.Kaiser, C.G.B.Garrett.Two-Photon Excitation in CaF
2: Eu
2+[J] .Phys.Rev.Lett.1961,7,229; Document [3]: the S.Singh that sees reference, L.T.Bradley.Three-Photon Absorption inNapthalene Crystals by Laser ExcitationPhys [J] .Rev.Lett.1964,12,612}.
Because organic materials has better chemical modification property; The inorganic materials research that tradition has multiphoton absorption slowly turns to organic multiphoton absorption material; Its goal in research is exactly to increase molecular conjugation plane length through chemical means; Increase its organic molecule and catch the ability of photon or electronics, cause the efficient of this type of material generation opto-electronic conversion or other energy transformation to improve.Therefore, how to utilize a kind of bigger molecular conjugation planar organic molecule material of chemical means design to become comparatively popular in recent years research topic.
Recent years is to preparation and synthetic existing a large amount of report { X.Wang, D.M.Nguyen, the C.O.Yanez with macromole conjugated system organic materials; L.Rodriguez, H.Y.Ahn, M.V.Bondar; AndK.D.Belfield, J.Am.Chem.Soc.2010,132; 12237}, but in some compounds of having reported, its photochemical stability is not strong; Particularly in the process of preparation film, be prone to decomposing phenomenon takes place, thereby restricted such application of molecular compound film in devices field.Therefore, design and invent a kind of have optical stability, thermostability and solvability preferably preferably macromole conjugated system organic materials become one of following said material major issue that demand solves in use in fields such as information storage, optics and ultra tiny laser processing.
Summary of the invention
Technical problem to be solved by this invention provides a kind of 2; 6-two (aromatic base)-anthraquinone and preparation method thereof; This compound has photochemical stability, thermostability and solvability preferably; It also has up-conversion lasing and fluorescence phenomenon simultaneously, thereby can satisfy many-sided application requiring such as light up-conversion and non-linear absorption material.
Technical solution of the present invention is following:
A kind of 2; 6-two (aromatic base)-anthraquinone and preparation method thereof is that electron donor(ED) or electron acceptor(EA) group are connected the anthraquinone ring both sides at 2,6; With 2; He Ke (Heck Reaction) reaction generation takes place in 6-dibromo-anthraquinone analog derivative and the substituted radical that contains vinyl under alkaline condition under the katalysis of palladium and three-O-methoxyl group phosphorus, its general formula of molecular structure is following:
Wherein: R is the substituted radical of vinyl, comprises electronic donor group or electron acceptor(EA) group.
Described electronic donor group is: 4-amino-benzene vinyl, 4-methoxyl-styrene, 4-phenetole vinyl, 4-fluorophenethyl thiazolinyl, 4-chloro-styrene base, 4-bromstyrol base, 4-methyl styryl, N-vinyl pyrrolidone, N-VCz; 1-vinyl-4; 6-two (ethylamino)-1; 3,5-triazine or 4-acetoxy-styrene base.The corresponding structure formula is following:
Described electron acceptor(EA) group comprises: 2-vinyl pyridine, 4-vinylpridine, 1-(4-vinylphenol)-1H-pyrroles-2; 5-diketone, 1-nitro-4-vinyl benzene, (4-styryl) diethyl phosphonate, 4-vinyl benzoic acid or 2-vinyl isoindoline-1, the 3-diketone.The corresponding structure formula is following:
The present invention 2, and the preparation method of 6-two (aromatic base)-anthraquinone, its characteristics are that this method is with described 2, and the substituted radical of 6-two bromo-anthraquinones and vinyl is through He Ke (Heck reaction) prepared in reaction 2,6-two (aromatic base)-anthraquinone, and its reaction formula is:
Concrete preparation process is following:
With 2 of 50～65mol%, 6-two bromo-anthraquinones, the aromatic base vinylbenzene of 20～30mol%, the palladium of 2～10mol%; Three-O-tolyl phosphorus of 2～10mol% under nitrogen protective atmosphere foxing spare, joins in the triethylamine solvent, stirs 24～72 hours at 60～120 ℃; Be cooled to room temperature, underpressure distillation, separating, washing; Dry concentrating obtains title product 2,6-two (aromatic base)-anthraquinone with the chromatography column separation.
In the final compound, the modification purpose of R group is the ability that increases the conjugate system transfer transport of whole molecule, and plays the effect of regulating absorbing wavelength and the solvability that increases compound.
Technique effect of the present invention is following:
The present invention 2, and 6-two (aromatic base)-anthraquinone modifies through chemical means 2,6 to macromole conjugation parent anthraquinone, increases its molecular conjugation plane.Simultaneously because the monomeric solvability of anthraquinone is relatively poor; Need could dissolve in the alcoholic solvent preferably in polarity, but through 2 of the inventive method preparation, 6-two (aromatic base)-anthraquinone; Improved the solvability of anthraquinone derivatives effectively; The solubility property of (like normal hexane, chloroform, THF, methylene dichloride, trichloromethane etc.) is all better in common common solvent, is convenient to be applied to the thin-film technique preparation.
Experiment also shows: the anthraquinone analog compound of the present invention's preparation also has optical stability and thermostability preferably; Under common illumination condition, be difficult for taking place photolysis; In the solid state powder of normal temperature, be difficult for taking place oxidation and decomposition simultaneously; Shelf time is long, has widened the applied technical field of anthraquinone derivative, can be widely used in fields such as information storage, optics and ultra tiny laser processing.
Embodiment
Below in conjunction with specific embodiment the present invention is described further, but they are not to qualification of the present invention.
Embodiment 1:
2, the preparation of 6-two (4-methoxyl-styrene)-anthraquinone comprises the following steps:
With 2,6-two bromo-anthraquinones (15 gram), 4-methoxy styrene (8.6 gram), palladium (0.9 gram), three-O-tolyl phosphorus (0.7 gram) under nitrogen protective atmosphere foxing spare, joins in the triethylamine solvent, 75 ℃ of stirring heating 48 hours.Reaction finishes postcooling to room temperature, underpressure distillation, separating, washing, dry concentrating.Obtain title product 2 with the chromatography column separation, 6-two (4-methoxyl-styrene)-anthraquinone, 11.8 grams, productive rate 73%.
Embodiment 2:
2,6-two (4-amino-benzene vinyl)-anthraquinone synthetic
With 2,6-two bromo-anthraquinones (15 gram), 4-amino-benzene ethene (9.2 gram), palladium (1.2 gram), three-O-tolyl phosphorus (0.7 gram) under nitrogen protective atmosphere foxing spare, joins in the triethylamine, 90 ℃ of stirring heating 48 hours.Reaction finishes postcooling to room temperature, underpressure distillation, separating, washing, dry concentrating.Obtain title product 2 with the chromatography column separation, 6-two (4-amino-benzene vinyl)-anthraquinone, 13.3 grams, productive rate 76%.
Embodiment 3:
2,6-two (4-chloro-styrene base)-anthraquinone synthetic
With 2,6-two bromo-anthraquinones (15 gram), 4-chloro-styrene (9.4 gram), palladium (1 gram), three-O-tolyl phosphorus (0.7 gram) under nitrogen protective atmosphere foxing spare, joins in the triethylamine, 90 ℃ of stirring heating 24 hours.Reaction finishes postcooling to room temperature, underpressure distillation, separating, washing, dry concentrating.Obtain title product 2 with the chromatography column separation, 6-two (4-chloro-styrene base)-anthraquinone, 9.4 grams, productive rate 65%.
Embodiment 4:
2,6-two (4-vinylpridine)-anthraquinone synthetic
With 2,6-two bromo-anthraquinones (15 gram), 4-vinylpridine (7.3 gram), palladium (1.6 gram), three-O-tolyl phosphorus (0.7 gram) under nitrogen protective atmosphere foxing spare, joins in the triethylamine, 95 ℃ of stirring heating 48 hours.Reaction finishes postcooling to room temperature, underpressure distillation, separating, washing, dry concentrating.Obtain title product 2 with the chromatography column separation, 6-two (4-vinylpridine)-anthraquinone, 14.9 grams, productive rate 82%.
Embodiment 5:
2,6-two (2-vinyl pyridine)-anthraquinone synthetic
With 2,6-two bromo-anthraquinones (15 gram), 2-vinyl pyridine (7.3 gram), palladium (1.7 gram), three-O-tolyl phosphorus (0.9 gram) under nitrogen protective atmosphere foxing spare, joins in the triethylamine, 85 ℃ of stirring heating 48 hours.Reaction finishes postcooling to room temperature, underpressure distillation, separating, washing, dry concentrating.Obtain title product 2 with the chromatography column separation, 6-two (2-vinyl pyridine)-anthraquinone, 13.5 grams, productive rate 74%.
Embodiment 6:
2,6-two (4-bromstyrol base)-anthraquinone synthetic
With 2,6-two bromo-anthraquinones (15 gram), 4-bromstyrol (13.1 gram), palladium (1.5 gram), three-O-tolyl phosphorus (0.8 gram) under nitrogen protective atmosphere foxing spare, joins in the triethylamine, 100 ℃ of stirring heating 48 hours.Reaction finishes postcooling to room temperature, underpressure distillation, separating, washing, dry concentrating.Obtain title product 2 with the chromatography column separation, 6-two (4-bromstyrol base)-anthraquinone, 16.3 grams, productive rate 62%.
Embodiment 7:
2,6-two (N-vinyl carbazole base)-anthraquinone synthetic
With 2,6-two bromo-anthraquinones (15 gram), N-VCz (24.2 gram), palladium (1.3 gram), three-O-tolyl phosphorus (0.8 gram) under nitrogen protective atmosphere foxing spare, joins in the triethylamine, 80 ℃ of stirring heating 36 hours.Reaction finishes postcooling to room temperature, underpressure distillation, separating, washing, dry concentrating.Obtain title product 2 with the chromatography column separation, 6-two (N-vinyl carbazole base)-anthraquinone, 12.7 grams, productive rate 53%.
Embodiment 8:
2,6-two (4-acetoxy-styrene base)-anthraquinone synthetic
With 2,6-two bromo-anthraquinones (15 gram), 4-acetoxy-styrene (26.8 gram), palladium (1.3 gram), three-O-tolyl phosphorus (0.9 gram) under nitrogen protective atmosphere foxing spare, joins in the triethylamine, 85 ℃ of stirring heating 40 hours.Reaction finishes postcooling to room temperature, underpressure distillation, separating, washing, dry concentrating.Obtain title product 2 with the chromatography column separation, 6-two (N-vinyl carbazole base)-anthraquinone, 14.6 grams, productive rate 72%.
Embodiment 9:
2,6-two (4-vinyl benzoic acid)-anthraquinone synthetic
With 2,6-two bromo-anthraquinones (15 gram), 4-vinyl benzoic acid (26.5 gram), palladium (1.3 gram), three-O-tolyl phosphorus (0.7 gram) under nitrogen protective atmosphere foxing spare, joins in the triethylamine, 90 ℃ of stirring heating 30 hours.Reaction finishes postcooling to room temperature, underpressure distillation, separating, washing, dry concentrating.Obtain title product 2 with the chromatography column separation, 6-two (4-vinyl benzoic acid)-anthraquinone, 13.7 grams, productive rate 63%.
Embodiment 10:
2,6-two (4-phenetole vinyl)-anthraquinone synthetic
With 2,6-two bromo-anthraquinones (15 gram), 4-phenetole ethene (19.4 gram), palladium (1.3 gram), three-O-tolyl phosphorus (0.8 gram) under nitrogen protective atmosphere foxing spare, joins in the triethylamine, 800 ℃ of stirring heating 36 hours.Reaction finishes postcooling to room temperature, underpressure distillation, separating, washing, dry concentrating.Obtain title product 2 with the chromatography column separation, 6-two (N-vinyl carbazole base)-anthraquinone, 14.7 grams, productive rate 83%.
Although the present invention has been done detailed explanation and has quoted some specific embodiments as proof, to those skilled in the art, only otherwise leave that the spirit and scope of the present invention can be done various variations and correction is obvious.
Claims (5)
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| CN103059834A (en) * | 2013-01-11 | 2013-04-24 | 中国科学院福建物质结构研究所 | Multiphoton Laser Materials |
| CN105837495A (en) * | 2016-03-24 | 2016-08-10 | 华南理工大学 | Preparation method and application of aromatic amino derivative substituted phenol or alkoxybenzene small-molecular hole-transport material |
| CN106800525A (en) * | 2016-12-14 | 2017-06-06 | 中节能万润股份有限公司 | A kind of fluorenyl Anthraquinones electroluminescent organic material and its preparation method and application |
| CN109950408A (en) * | 2019-04-15 | 2019-06-28 | 北京化工大学 | A kind of polymer solar cell and preparation method thereof |
| CN114195630A (en) * | 2021-10-26 | 2022-03-18 | 湖南五江高科技材料有限公司 | Synthesis method of 9, 10-dialkoxy anthracene serving as photocuring initiator |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103059834A (en) * | 2013-01-11 | 2013-04-24 | 中国科学院福建物质结构研究所 | Multiphoton Laser Materials |
| CN103059834B (en) * | 2013-01-11 | 2017-04-05 | 中国科学院福建物质结构研究所 | multiphoton laser material |
| CN105837495A (en) * | 2016-03-24 | 2016-08-10 | 华南理工大学 | Preparation method and application of aromatic amino derivative substituted phenol or alkoxybenzene small-molecular hole-transport material |
| CN105837495B (en) * | 2016-03-24 | 2018-09-14 | 华南理工大学 | The preparation and application of aromatic amino-derivative fortified phenol or alkoxy benzene small molecule hole transport material |
| CN106800525A (en) * | 2016-12-14 | 2017-06-06 | 中节能万润股份有限公司 | A kind of fluorenyl Anthraquinones electroluminescent organic material and its preparation method and application |
| CN106800525B (en) * | 2016-12-14 | 2019-04-02 | 中节能万润股份有限公司 | A kind of fluorenyl Anthraquinones electroluminescent organic material and its preparation method and application |
| CN109950408A (en) * | 2019-04-15 | 2019-06-28 | 北京化工大学 | A kind of polymer solar cell and preparation method thereof |
| CN114195630A (en) * | 2021-10-26 | 2022-03-18 | 湖南五江高科技材料有限公司 | Synthesis method of 9, 10-dialkoxy anthracene serving as photocuring initiator |
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