CN1730467A - Novel LCD compound p-isoamoxy cinnamic acid -2-fluoro-4-hydroxy- benzonitrile ester and its preparation method - Google Patents
Novel LCD compound p-isoamoxy cinnamic acid -2-fluoro-4-hydroxy- benzonitrile ester and its preparation method Download PDFInfo
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- CN1730467A CN1730467A CN200510043712.2A CN200510043712A CN1730467A CN 1730467 A CN1730467 A CN 1730467A CN 200510043712 A CN200510043712 A CN 200510043712A CN 1730467 A CN1730467 A CN 1730467A
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- fluoro
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- hydroxy
- isopentyloxy
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- -1 cinnamic acid -2-fluoro-4-hydroxy- benzonitrile ester Chemical class 0.000 title claims description 14
- 239000004973 liquid crystal related substance Substances 0.000 claims abstract description 30
- 238000009833 condensation Methods 0.000 claims abstract description 3
- 230000005494 condensation Effects 0.000 claims abstract description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 12
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- NQBWNECTZUOWID-UHFFFAOYSA-N (E)-cinnamyl (E)-cinnamate Natural products C=1C=CC=CC=1C=CC(=O)OCC=CC1=CC=CC=C1 NQBWNECTZUOWID-UHFFFAOYSA-N 0.000 claims description 10
- 125000005921 isopentoxy group Chemical group 0.000 claims description 7
- NGSWKAQJJWESNS-ZZXKWVIFSA-M 4-Hydroxycinnamate Natural products OC1=CC=C(\C=C\C([O-])=O)C=C1 NGSWKAQJJWESNS-ZZXKWVIFSA-M 0.000 claims description 6
- DFYRUELUNQRZTB-UHFFFAOYSA-N Acetovanillone Natural products COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 claims description 6
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 6
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
- 239000006227 byproduct Substances 0.000 claims description 4
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 4
- 239000012046 mixed solvent Substances 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract description 2
- 229930016911 cinnamic acid Natural products 0.000 abstract description 2
- 235000013985 cinnamic acid Nutrition 0.000 abstract description 2
- 150000001851 cinnamic acid derivatives Chemical class 0.000 abstract description 2
- 230000018044 dehydration Effects 0.000 abstract description 2
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract description 2
- REIVHYDACHXPNH-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzonitrile Chemical class OC1=CC=C(C#N)C(F)=C1 REIVHYDACHXPNH-UHFFFAOYSA-N 0.000 abstract 1
- NAORGNSYBDQEPT-UHFFFAOYSA-N 3-phenylprop-2-enoic acid Chemical group OC(=O)C=CC1=CC=CC=C1.OC(=O)C=CC1=CC=CC=C1 NAORGNSYBDQEPT-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000460 chlorine Chemical group 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000012769 display material Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention relates to a fluorocyano-containing cinnamic ester liquid crystal compound and its preparing process, the compound has a chemical structure of para-isopentyloxy cinnamic acid-2-fluoro-4-hydroxybenzene nitrile ester, the preparation process comprises introducing alkoxy to 4-position of cinnamic acid (3-phenylacrylic acid) through Williamson etherification reaction, then carrying out DCC dehydration condensation, so as to make the substituted cinnamic acid and 2-fluoro-4-hydroxybenzene nitrile condense and produce needed compound. The invention also discloses the use of the compound, which can be used in not only mixed liquid crystal, but also in various LCDs.
Description
Technical field
The present invention relates to technical field of organic synthesis, especially relate to a kind of substituted cinnamic acid ester class organic lcd compound and preparation method and purposes that contains fluorine atom and cyano group.
Background technology
In recent years, liquid crystalline cpd and liquid crystal material become one of focus of applied chemistry and materials chemistry research, obtained widely using in each side such as electronics, optics, acoustics, biotechnology, chemical industry, and wherein the most extensive and the most important thing is its application aspect the electronics demonstration.Along with the development of information industry, to the requirement of liquid crystal material also in continuous raising.Though the report of relevant liquid crystal material aspect is existing a lot, but they all are not suitable in the display device, must satisfy requirements such as broad operating temperature range, lower operating voltage, low-viscosity, response fast, high stability because show the liquid crystal material of usefulness.
With 2-fluoro-4-4-hydroxy-benzonitrile is the advantage that the liquid crystalline cpd of intermediate has fluorinated liquid crystal and cyano group liquid crystal concurrently, be the important liquid crystalline cpd of a class that satisfies above-mentioned condition, represents the liquid crystal development trend, and therefore 2-fluoro-4-4-hydroxy-benzonitrile also become intermediate important in the liquid crystal chemical industry.This intermediate is at first the most synthetic by Japanese Sumitomo Chemical Co.Ltd. as far back as nineteen eighty-two, after this people use this intermediate to synthesize hundreds of liquid crystalline cpds, these compounds all have the advantage of high clearing point, wide liquid crystal working range, low-viscosity, are suitable as the moiety of the demonstration liquid crystal material of excellent property.
Summary of the invention
The purpose of this invention is to provide a kind of substituted cinnamic acid esters liquid crystal compound that contains fluorine atom and cyano group, its structural formula is
This compound has the advantage that chemical property is stable, clearing point is high, liquid crystal range is wide, is the desirable moiety of liquid crystal display material.
This compound is made by organic synthesis technology.The main points of the method for synthetic this compound are:
1) with the ethanol-water solution be mixed solvent, wherein the alcoholic acid volume percent is 70%～95%; Adding soluble alkali metal oxyhydroxide makes the potential of hydrogen of solution reach pH＞10, in solvent, add halo iso-pentane (halogen atom comprises fluorine, chlorine, bromine atoms) and p-Coumaric Acid, the ratio of both amount of substances is 2～5: 1, and the massfraction of p-Coumaric Acid in solution is 5%～30%.Under this condition, make both that condensation reaction take place.Temperature of reaction is 50～80 ℃.
2) after condensation reaction finishes, react, remove the by product that generates in the step 1), make pure the isopentyloxy styracin by hydrolysis reaction with the ethanol-water mixed solvent solution of soluble alkali metal oxyhydroxide mixed solution with previous step reaction gained.The ratio of the amount of substance of employed p-Coumaric Acid is 2～5: 1 in used solubility oxyhydroxide and the step 1), the pH of reaction system＞12, and temperature of reaction is 50～80 ℃, the alcoholic acid volume percent is 60%～80% in the mixed solvent.
X＝Cl，Br，I
3) with DCC (N, the N-dicyclohexylcarbodiimide) is dewatering agent, DMAP (N, the N-Dimethylamino pyridine) is catalyzer, anhydrous tetrahydro furan is a solvent, impel isopentyloxy styracin and 2-fluoro-4-4-hydroxy-benzonitrile are passed through dehydration condensation, generate target compound isopentyloxy styracin-2-fluoro-4-4-hydroxy-benzonitrile ester.DCC, be 1～1.5: 1～2 to the ratio of the amount of substance of isopentyloxy styracin, 2-fluoro-4-4-hydroxy-benzonitrile, DMAP: 1: 0.01～0.02, the initial mass mark of 2-fluoro-4-4-hydroxy-benzonitrile in solution is 5%～20%.Temperature of reaction is 0～30 ℃.
To help to understand the present invention by following experiment, but following experiment does not limit content of the present invention.
Implement 1
1) 0.01mol p-Coumaric Acid and 0.02mol potassium hydroxide are dissolved in 40ml95% (volume fraction) ethanol, speed with about 1ml/min dropwise adds 0.03mol bromo iso-pentane again, back flow reaction 24h, 70% (volume fraction) ethanolic soln meter 14ml that adds 0.02mol potassium hydroxide again continues backflow 2h.Add entry 100ml, concentrated hydrochloric acid 20ml, behind the heating 15min, cold filtration with distilled water wash, drying, with 95% (volume fraction) ethyl alcohol recrystallization, obtains the isopentyloxy styracin again, is the white plates crystal, productive rate 54%.
2) in there-necked flask, add 0.01mol to isopentyloxy styracin and 20ml anhydrous tetrahydro furan, after stirring is dissolved it fully, DCC (the N that adds 0.01mol, the N-dicyclohexylcarbodiimide), after waiting to become turbid, with 0.01mol2-fluoro-4-4-hydroxy-benzonitrile and a small amount of DMAP[4-(N, the N-dimethylamino) pyridine] be dissolved in wiring solution-forming in the 20ml anhydrous tetrahydro furan, slowly splash in the flask, about 10 ℃, stir 24h, after reaction finishes, remove by filter by product N, the N-dicyclohexylurea (DCU), adding distil water is precipitated out product in filtrate, dry back gets pure product 0.55g by column chromatography for separation, productive rate about 15%.
Implement 2
1) 0.02mol p-Coumaric Acid and 0.05mol potassium hydroxide are dissolved in 100ml95% (volume fraction) ethanol, add 0.03mol bromo iso-pentane again, back flow reaction 48h.70% (volume fraction) ethanolic soln meter 35ml that adds 0.03mol potassium hydroxide afterwards continues backflow 2h.Add entry 100ml, concentrated hydrochloric acid 40ml mixes, and behind the heating 20min, cold filtration with distilled water wash, drying, with 95% (volume fraction) ethyl alcohol recrystallization, obtains the isopentyloxy styracin again, is the white plates crystal, productive rate 49%.
2) in there-necked flask, add 0.015mol to isopentyloxy styracin and 50ml anhydrous tetrahydro furan, after stirring is dissolved it fully, DCC (the N that adds 0.01mol, the N-dicyclohexylcarbodiimide), after waiting to become turbid, with 0.015mol2-fluoro-4-4-hydroxy-benzonitrile and a small amount of DMAP[4-(N, the N-dimethylamino) pyridine] be dissolved in wiring solution-forming in the 35ml anhydrous tetrahydro furan fully, slowly splash in the flask, about 20 ℃, stir 24h, after reaction finishes, remove by filter by product N, the N-dicyclohexylurea (DCU), adding distil water is precipitated out product in filtrate, dry back gets pure product 0.85g by column chromatography for separation, productive rate about 17%.
By IR,
1H NMR method characterizes institute's synthetic compound, to confirm its structure.
IR (infrared spectra):
Cyano group (1, the stretching vibration of C ≡ N key, 2231cm
-1)
Phenyl ring (2, the stretching vibration of phenyl ring carbon skeleton, 1602,1572,1515cm
-1)
Carbonyl (3, C=O stretching vibration, 1729cm
-1)
Carbon oxygen singly-bound (4, C-O-C stretching vibration, 1254,1116cm
-1)
1HNMR (proton nmr spectra):
Proton 1: δ=6.74 * 10
-6, s=0.96
Proton 2: δ=7.02 * 10
-6, s=2.01
Proton 3: δ=7.78 * 10
-6, s=1.99
Proton 4: δ=7.35 * 10
-6, s=0.98
Proton 5: δ=7.62 * 10
-6, s=1.0
Proton 6: δ=7.87 * 10
-6, s=0.96
Proton 7: δ=8.05 * 10
-6, s=0.94
Proton 8: δ=0.94 * 10
-6, s=6.09
Proton 9: δ=1.78 * 10
-6, s=1.06
Proton 10: δ=1.63 * 10
-6, s=2.08
Proton 11: δ=4.06 * 10
-6, s=1.98
The structure of confirming institute's synthetic compound thus is consistent with expection.
By DSC (differential calorimetric scanning) and POM (orthogonal polarizing microscope) the liquid crystal phase transition character of institute's synthetic compound is characterized.
The transformation behavior of finding institute's synthetic compound by differential calorimetric scanning analysis is:
K?98.9I(82.4)N(42.3)K
The transformation behavior that meets thermotropic liquid crystal.
By orthogonal polarizing microscope institute's synthetic sample is observed, sample is a needle-like crystal under the normal temperature, is placed on the hot platform of polarizing microscope to heat sample fusion during to about 100 ℃, the visual field presents the even black of a slice, illustrates after crystal fuses directly to become isotropic liquid.Be heated to 120 ℃ it is fully fused, lower the temperature with the speed of 5 ℃/min again.To about 84 ℃, show typical striped texture, and have the point of crossing of sending four black schlierens in a large number, show that having intensity in the mesomorphic phase is+2 point defect.This proves absolutely that this moment, sample presented nematic phase.Be cooled to about 35 ℃, mesomorphic phase generation crystallization.This phase behavior shows that to isopentyloxy styracin-2-fluoro-4-4-hydroxy-benzonitrile ester be monotropic thermotropic liquid crystal.
More than explanation is suitable as the ideal moiety of liquid crystal composite used in the liquid-crystal display, is suitable in the used liquid crystal composite material of liquid-crystal displays such as TN, STN, TFT isopentyloxy styracin-2-fluoro-4-4-hydroxy-benzonitrile ester about the test result of liquid crystal property.
Claims (4)
- One kind novel liquid crystal compound-to isopentyloxy styracin-2-fluoro-4-4-hydroxy-benzonitrile ester, its structural formula is
- 2. a novel liquid crystal compound-, it is characterized in that to the preparation method of isopentyloxy styracin-2-fluoro-4-4-hydroxy-benzonitrile ester1) under the potential of hydrogen of pH＞10,50～80 ℃ temperature, halo iso-pentane and p-Coumaric Acid are condensed into the isopentyloxy styracin by the Williamson condensation reaction,2) after condensation finishes, under 50～80 ℃ of conditions, remove reactions steps 1 by hydrolysis reaction with the solution of highly basic in ethanol-water mixed solvent) in the by product that generates,3) with DCC (N, the N-dicyclohexylcarbodiimide) be dewatering agent, DMAP (N, N-Dimethylamino pyridine) is a catalyzer, 0～30 ℃ of reaction down, impel isopentyloxy styracin and the paired isopentyloxy styracin of 2-fluoro-4-4-hydroxy-benzonitrile dehydrating condensation-2-fluoro-4-4-hydroxy-benzonitrile ester.
- One kind novel liquid crystal compound-to the isopentyloxy styracin-application of 2-fluoro-4-4-hydroxy-benzonitrile ester in the liquid crystal that is mixed, containing with structural formula (1) in the liquid crystal that it is characterized in that being mixed is the compound of feature.
- 4. a kind of novel liquid crystal compound as claimed in claim 3-, it is characterized in that containing with structural formula (1) between the liquid-crystal display electrode pair is the compound of feature to the isopentyloxy styracin-application of 2-fluoro-4-4-hydroxy-benzonitrile ester in the liquid crystal that is mixed.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100437122A CN1315796C (en) | 2005-06-08 | 2005-06-08 | Novel LCD compound p-isoamoxy cinnamic acid -2-fluoro-4-hydroxy- benzonitrile ester and its preparation method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2005100437122A CN1315796C (en) | 2005-06-08 | 2005-06-08 | Novel LCD compound p-isoamoxy cinnamic acid -2-fluoro-4-hydroxy- benzonitrile ester and its preparation method |
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| Publication Number | Publication Date |
|---|---|
| CN1730467A true CN1730467A (en) | 2006-02-08 |
| CN1315796C CN1315796C (en) | 2007-05-16 |
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Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1315796C (en) |
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