CN106398714A - 苯乙炔类液晶材料的制备方法 - Google Patents
苯乙炔类液晶材料的制备方法 Download PDFInfo
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- CN106398714A CN106398714A CN201510460610.4A CN201510460610A CN106398714A CN 106398714 A CN106398714 A CN 106398714A CN 201510460610 A CN201510460610 A CN 201510460610A CN 106398714 A CN106398714 A CN 106398714A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 39
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 239000000463 material Substances 0.000 title claims abstract description 31
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 238000000746 purification Methods 0.000 claims abstract description 22
- 239000003960 organic solvent Substances 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 5
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 84
- 239000000047 product Substances 0.000 claims description 61
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 58
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 51
- 239000012074 organic phase Substances 0.000 claims description 47
- 238000000605 extraction Methods 0.000 claims description 45
- 239000007787 solid Substances 0.000 claims description 43
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
- 239000003208 petroleum Substances 0.000 claims description 27
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 239000000376 reactant Substances 0.000 claims description 24
- 238000010992 reflux Methods 0.000 claims description 22
- 238000003756 stirring Methods 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- 238000000967 suction filtration Methods 0.000 claims description 16
- 238000002390 rotary evaporation Methods 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000012264 purified product Substances 0.000 claims description 12
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 8
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 8
- LXWJYIBQIPSFSE-UHFFFAOYSA-N dipotassium;nickel(2+);tetracyanide Chemical compound [K+].[K+].[Ni+2].N#[C-].N#[C-].N#[C-].N#[C-] LXWJYIBQIPSFSE-UHFFFAOYSA-N 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 235000019270 ammonium chloride Nutrition 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000007853 buffer solution Substances 0.000 claims description 6
- 235000010288 sodium nitrite Nutrition 0.000 claims description 6
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 6
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 5
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 3
- CURJNMSGPBXOGK-UHFFFAOYSA-N n',n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)N(C(C)C)CCN CURJNMSGPBXOGK-UHFFFAOYSA-N 0.000 claims description 3
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 claims description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 3
- 239000011592 zinc chloride Substances 0.000 claims description 3
- 235000005074 zinc chloride Nutrition 0.000 claims description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000007928 solubilization Effects 0.000 claims 1
- 238000005063 solubilization Methods 0.000 claims 1
- 150000007984 tetrahydrofuranes Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 12
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- -1 cyclohexylidene, phenylene Chemical group 0.000 abstract 2
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 description 37
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 32
- 238000004440 column chromatography Methods 0.000 description 25
- 230000008878 coupling Effects 0.000 description 23
- 238000010168 coupling process Methods 0.000 description 23
- 238000005859 coupling reaction Methods 0.000 description 23
- 239000012467 final product Substances 0.000 description 23
- 229910052786 argon Inorganic materials 0.000 description 16
- 238000001914 filtration Methods 0.000 description 16
- 239000007789 gas Substances 0.000 description 16
- 239000012043 crude product Substances 0.000 description 15
- 238000005406 washing Methods 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
- 238000000944 Soxhlet extraction Methods 0.000 description 12
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000007789 sealing Methods 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 4
- GZRMNMGWNKSANY-UHFFFAOYSA-N 4-bromo-2-fluoroaniline Chemical compound NC1=CC=C(Br)C=C1F GZRMNMGWNKSANY-UHFFFAOYSA-N 0.000 description 3
- 0 CC(C)(C1*C*CC1)C1=CCC(C(C)(C)C#CC2C=C(*)C(C#N)=C(*)C2)C=C1 Chemical compound CC(C)(C1*C*CC1)C1=CCC(C(C)(C)C#CC2C=C(*)C(C#N)=C(*)C2)C=C1 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- ADYWBFBXUJFLII-UHFFFAOYSA-N 4-bromo-n-fluoroaniline Chemical compound FNC1=CC=C(Br)C=C1 ADYWBFBXUJFLII-UHFFFAOYSA-N 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 238000012805 post-processing Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- RLJXJUHMVYLIBW-UHFFFAOYSA-N 1,2,3-trifluoro-5-iodobenzene Chemical class FC1=CC(I)=CC(F)=C1F RLJXJUHMVYLIBW-UHFFFAOYSA-N 0.000 description 1
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 1
- BLDJYKKRRVISJT-UHFFFAOYSA-N 1-ethynyl-4-heptylcyclohexane Chemical group CCCCCCCC1CCC(C#C)CC1 BLDJYKKRRVISJT-UHFFFAOYSA-N 0.000 description 1
- QVMNQCZRJUORAR-UHFFFAOYSA-N 1-ethynyl-4-pentoxycyclohexane Chemical group C(CCCC)OC1CCC(CC1)C#C QVMNQCZRJUORAR-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- NWAYGDHZGKCPRY-UHFFFAOYSA-N acetylene;1-pentyl-4-phenylbenzene Chemical group C#C.C1=CC(CCCCC)=CC=C1C1=CC=CC=C1 NWAYGDHZGKCPRY-UHFFFAOYSA-N 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KSPLOOKXNGXEKI-UHFFFAOYSA-N but-1-ynylcyclohexane Chemical group CCC#CC1CCCCC1 KSPLOOKXNGXEKI-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
Claims (14)
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111065712A (zh) * | 2017-09-14 | 2020-04-24 | 默克专利股份有限公司 | 异硫氰酸基二苯乙炔衍生物 |
CN112831324A (zh) * | 2020-12-31 | 2021-05-25 | 苏州汉朗光电有限公司 | 一种快速响应的液晶组合物材料 |
CN114940844A (zh) * | 2022-06-16 | 2022-08-26 | 西北工业大学 | 一种基于光响应的液晶型防伪油墨及其制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0442266A1 (en) * | 1989-11-29 | 1991-08-21 | Seiko Epson Corporation | Tolan derivatives, liquid crystal compositions containing them, and liquid crystal elements using them |
-
2015
- 2015-07-31 CN CN201510460610.4A patent/CN106398714B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0442266A1 (en) * | 1989-11-29 | 1991-08-21 | Seiko Epson Corporation | Tolan derivatives, liquid crystal compositions containing them, and liquid crystal elements using them |
Non-Patent Citations (2)
Title |
---|
彭增辉等: "氟代苯基二苯乙炔基异硫氰酸酯的合成与液晶性质研究", 《液晶与显示》 * |
耿同谋: "二氯硫化碳合成的改进", 《黄淮学刊》 * |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111065712A (zh) * | 2017-09-14 | 2020-04-24 | 默克专利股份有限公司 | 异硫氰酸基二苯乙炔衍生物 |
CN111065712B (zh) * | 2017-09-14 | 2023-07-04 | 默克专利股份有限公司 | 异硫氰酸基二苯乙炔衍生物 |
US11891557B2 (en) * | 2017-09-14 | 2024-02-06 | Merck Patent Gmbh | Isothiocyanato tolane derivatives |
CN112831324A (zh) * | 2020-12-31 | 2021-05-25 | 苏州汉朗光电有限公司 | 一种快速响应的液晶组合物材料 |
CN112831324B (zh) * | 2020-12-31 | 2023-03-10 | 重庆汉朗精工科技有限公司 | 一种快速响应的液晶组合物材料 |
CN114940844A (zh) * | 2022-06-16 | 2022-08-26 | 西北工业大学 | 一种基于光响应的液晶型防伪油墨及其制备方法 |
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