CN1229119A - Ferroelectric type fluorine-containing steroid liquid crystal, preparation method and its use - Google Patents
Ferroelectric type fluorine-containing steroid liquid crystal, preparation method and its use Download PDFInfo
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- CN1229119A CN1229119A CN 99113424 CN99113424A CN1229119A CN 1229119 A CN1229119 A CN 1229119A CN 99113424 CN99113424 CN 99113424 CN 99113424 A CN99113424 A CN 99113424A CN 1229119 A CN1229119 A CN 1229119A
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Abstract
A ferroelectric-type fluorine containing setroid kind of liquid crystal, its preparing process and its application are disclosed. Said compound has a special structure described in the specification of present invention.
Description
The present invention relates to a kind of organic steroid, specifically a kind of ferroelectric type fluorine-containing steroid liquid crystal, preparation method and its usage.
Since finding liquid crystal in 1888,, in information display technology, chemical industry, obtained to use widely because liquid crystal has the character of many uniquenesses.With fluorine atom replace one or two hydrogen in the liquid crystal nuclear can effectively reduce liquid crystal viscosity, improve chemistry and light stability, replace atom [JP02,11570 (90,11570) on the flexible side-chains that is connected liquid crystal nuclear two ends with fluorine atom; JP01,283258 (89,283258)], also obtained ideal results.People such as Wen Jianxun once reported the liquid crystalline cpd that contains perfluoro-benzene-ring, and (CN 9210844.7, CN 97106778.3), having that transformation temperature is low, clearing point is high, viscosity is low, liquid crystal phase temperature range is wide, degree of birefringence is high, chemical stability is good and fat-soluble characteristic such as good, is a kind of liquid crystal material with wide application prospect.
The sterol ester liquid crystal is the liquid crystal material of cholesteric phase of excellent performance, is actually used in the dispensing liquid crystal.And in this class liquid crystalline cpd molecule, introduce the phenyl ring contain a fluorine, can improve its performance, once reported the cholesterol neighbour, to and a position single fluorine substituted benzoyl acid esters [Acta Phys.Chem., 1979,25 (3-4), 173-8; JP59,161,399 (1984)].People such as Wen Jianxun have reported a kind of sterol polyfluoro aromatic ester liquid crystal, have following molecular formula:
N=2 or 3 wherein, A=singly-bound or HC=CH, B=5, the two keys or 5 of 6-, 6-dihydro (CN9811084.3).Ferroelectric liquid crystals has advantages such as the good response speed of memory is fast, wherein has chiral smectic C phase (Sc
*) ferroelectric liquid crystals the most common, be the liquid crystal material of present widespread use.But cholesteryl phase all appears in Bao Dao fluorine-containing steroid liquid crystal in phase transition process so far, does not see the report of the fluorine-containing steroid liquid crystal of ferroelectric phase.Because the huge applications potentiality of liquid crystal material, people are still at the liquid crystal material of constantly exploring excellent property.
The purpose of this invention is to provide a kind of ferroelectric type fluorine-containing steroid liquid crystal.
Purpose of the present invention also provides the preparation method of this ferroelectric type fluorine-containing steroid liquid crystal.
Another object of the present invention provides the purposes of this ferroelectric type fluorine-containing steroid liquid crystal.Ferroelectric type fluorine-containing steroid liquid crystal of the present invention has following structural formula:
N=1-12 wherein, m=1 or 2, A=singly-bound, O, S, NH, CH
2CH
2Or CH=CH, B=singly-bound or S, D=5,6-dihydro or 5, the two keys of 6-, R=C
2-12Alkyl, thiazolinyl, alkyl acid methoxycarbonyl or ethoxycarbonyl, X=H, F or Cl.Described R group comprises CH (CH
3) CH
2CH
2CH
2CH (CH
3)
2, CH (CH
3) CH
2CH
2CO
2CH
3, CH (CH
3) CH
2CH
2CO
2C
2H
5, CH (CH
3) CH
2CH
2CH (C
2H
5) CH (CH
3)
2, CH (CH
3) CH=CHCH (CH
3) CH (CH
3)
2Or CH (CH
3) CH=CH
2Deng.Ferroelectric type fluorine-containing steroid liquid crystal of the present invention comprises following structural formula, but is not so limited:
Ferroelectric type fluorine-containing steroid liquid crystal of the present invention can be by 1. to perfluoroalkyl benzoyl chlorine or bromine and sterol or steroid thiol reactant; 2. to perfluoroalkyl phenol, to the perfluoroalkyl thiophenol or to the reaction of Perfluoroalkylanilin and sterol chloro-formic ester; Perhaps, 3. to the perfluoroalkyl phenylformic acid, make with sterol generation esterification to the perfluoroalkyl styracin or to perfluoroalkyl dihydro cinnamon acid, concrete preparation method is described below: (1) to perfluoroalkyl benzoyl chlorine or bromine,
The organic amine compound that has lone-pair electron on the nitrogen-atoms, their mol ratio is followed successively by 1: 0.7-2: during 0.7-10, reacted 10-100 hour under the room temperature in solvent, can generate:
(2) to perfluoroalkyl phenol or thiophenol
Or S-H or to Perfluoroalkylanilin
The sterol chloro-formic ester
The organic amine compound mol ratio that has lone-pair electron on the nitrogen-atoms is 1: 0.7-2: during 0.7-10, reacted 10-60 hour under the room temperature in solvent, can generate:
(3) to the perfluoroalkyl phenylformic acid, to the perfluoroalkyl styracin or to the acid of perfluoroalkyl dihydro cinnamon
Dewatering agent and catalyst molar ratio are followed successively by 1: 0.8-5: 0.5-5: during 0-0.10, in the presence of solvent in room temperature to reflux temperature under reaction can make respectively in 10-80 hour
The organic amine compound that has lone-pair electron on the described nitrogen-atoms can be C
1-24Primary amine, stretch amine or tertiary amine, as Trimethylamine 99, diethylamine, triethylamine, methylbenzylamine, trioctylamine, dilaurylamine etc., also can be pyridine, picoline, bipyridine, Tetramethyl Ethylene Diamine, tetraethylethylenediamine etc.Described dewatering agent is N, N-dicyclohexyl phosphinylidyne diimine (DCC).Described catalyzer is N, N '-dimethyl amine pyridine (DMAP).Wherein A, B, D, R or n are ditto described, E=Dan Jian, CH=CH or CH
2CH
2
Ferroelectric type fluorine-containing steroid liquid crystal of the present invention is simple synthetic method not only, and chiral source is inexpensive, the productive rate height, and present the ferroelectric liquid crystals performance, be a kind of ferroelectric liquid crystal material that is suitable for industrial production and application.
To help to understand the present invention by following embodiment, but not place restrictions on content of the present invention.Embodiment 1.
In a dry egg type bottle, add cholesterol 1g (2.59mmol), right-perfluoro hexyl phenylformic acid 1.4g (3.18mmol), N, N '-dicyclohexyl phosphinylidyne diimine (DCC) 2g (9.71mmol), N, N dimethylamine yl pyridines (DMAP) 0.1g and adjacent chloro-trifluoromethyl benzene 50ml, back flow reaction 48 hours.The reaction solution decompressing and extracting gets product 2g with the silicagel column flash chromatography, productive rate 95.5%.
MS(m/z)：441，368。
IR(KBr)υ(cm
-1)：1710。
1H?NMR(CDCl
3)δ：8.19(d，2H)，7.68(d，2H)，5.55(d，1H)，4.94(m，1H)。
19F?NMR(CDCl
3)δ：3.5(m，3F)，34.0(m，2F)，44.5(m，4F)，48.5(m，4F)。Embodiment 2
In a dry egg type bottle, add Dihydrocholesterol 1g (2.58mmol), right-perfluoro capryl phenylformic acid 1.8g (3.33mmol), DCC 2g (9.71mmol), N, N dimethylamine yl pyridines (DMAP) 0.1g and 1,2-ethylene dichloride 50ml, back flow reaction 48 hours.The reaction solution decompressing and extracting gets product 2.3g with the silicagel column flash chromatography, productive rate 98.1%.
MS(m/z)：541，370。IR(KBr)υ(cm
-1)：1722。
1H?NMR(CDCl
3)δ：8.17(d，2H)，7.67(d，2H)，4.98(m，1H)。
19F?NMR(CDCl
3)δ：3.77(m，3F)，34.22(2F)，44.27(s，2F)，44.90(s，6F)，
45.79(s，2F)，49.19(s，2F)。Embodiment 3
In a dry egg type bottle, add 3 beta-hydroxies-5-cholenic acid methyl esters 0.5g (1.29mmol), right-perfluoro butyl Benzoyl chloride 0.5g (1.46mmol), triethylamine 0.5ml and tetracol phenixin 25ml, room temperature reaction 24 hours.The reaction solution washing, Na
2SO
4Dry back evaporate to dryness.Rapid column chromatography gets product 0.91g, productive rate 99.3%.
MS(m/z)：370，341。
IR(KBr)υ(cm
-1)：1719。
1H?NMR(CDCl
3)δ：8.18(d，2H)，7.68(d，2H)，5.44(d，1H)，4.94(m，1H)。
19F?NMR(CDCl
3)δ：4.9(s，3F)，34.7(s，2F)，46.3(s，2F)，49.2(s，2F)。Embodiment 4
In a dry egg type bottle, add cholesterol chloro-formiate 1.0g (2.23mmol), right-perfluoro hexyl phenol 0.8g (1.94mmol), pyridine 0.3ml and methylene dichloride 20ml, room temperature reaction 36 hours.The reaction solution washing, MgSO
4Dry back decompressing and extracting, rapid column chromatography gets product 1.56g, productive rate 97.6%.
MS(m/z)：368。
IR(KBr)υ(cm
-1)：1760。
1H?NMR(CDCl
3)δ：7.35-7.65(dd，4H)，5.40-5.45(m，1H)，4.55-4.65(m，1H)。
19F?NMR(CDCl
3)δ：3.78(t，3F)，33.26(m，2F)，44.39～44.70(m，4F)，45.73(m，2F)，49.04(m，2F)。Embodiment 5
In a dry egg type bottle, add cholesterol chloro-formiate 0.4g (0.89mmol), right-perfluoro capryl aniline 0.4g (0.78mmol), triethylamine 0.3ml and methylene dichloride 20ml, room temperature reaction 48 hours, reaction solution washing, NaSO
4Dry back decompressing and extracting.Column chromatography gets product 0.7g, productive rate 97%.
MS(m/z)：556，368。
IR(KBr)υ(cm
-1)：3353，1720。
1H?NMR(CDCl
3)δ：7.52(m，4H)，6.77(s，1H)，5.42(d，1H)，4.62(m，1H)。
19F?NMR(CDCl
3)δ：3.76(m，3F)，33.29(m，2F)，44.37(s，2F)，45.01(s，6F)，
45.81(s，2F)，49.21(s，2F)。Embodiment 6
In a dry egg type bottle, add courage steroid mercaptan 100mg (0.25mmol), right-fluorine hexyl benzene formyl chloride 140g (0.31mmol), pyridine 0.1ml and methylene dichloride 10ml, room temperature reaction 50 hours.The reaction solution washing, Na
2SO
4Dry back decompressing and extracting.Column chromatography gets product 190mg, productive rate 92%.
MS(m/z)：456，368。
IR(KBr)υ(cm
-1)：1690。
1H?NMR(CDCl
3)δ：8.17(d，2H)，6.70(d，2H)，5.35(d，1H)，3.28(m，1H)。
19F?NMR(CDCl
3)δ：3.6(t，3F)，33.9(m，2F)，44.5(s，4F)，48.4(m，4F)，
45.81(s，2F)，49.21(s，2F)。Embodiment 7
In a dry egg type bottle, add Dihydrocholesterol 0.5g (1.29mmol), right-perfluoro butyl styracin 0.5g (1.37mmol), DCC0.4g (1.44mmol), DMAP50mg and toluene 30ml, back flow reaction 72 hours, column chromatography gets product 0.89g after the reaction solution decompressing and extracting, productive rate 93.7%.
MS(m/z)：736。
IRKBr)υ(cm
-1)：1710。
1H?NMR(CDCl
3)δ：7.55(d，1H)，7.14(m，4H)，6.38(d，2H)，4.82(m，1H)。
19F?NMR(CDCl
3)δ：3.9(s，3F)，34.3(s，2F)，45.8(s，2F)，49.0(s，2F)。Embodiment 8
In a dry egg type bottle, add β-Gu Zaichun 0.5g (1.21mmol), right-perfluoro hexyl dihydro cinnamon acid 0.6g (1.28mmol), DCC0.4g (1.94mmol), DMAP50mg and 1,2-ethylene dichloride 40ml, back flow reaction 60 hours.Reaction solution decompressing and extracting, column chromatography get product 1.0g, productive rate 95.7%.
MS(m/z)：396，451。
IR(KBr)υ(cm
-1)：1735。
1H?NMR(CDCl
3)δ：7.50(m，4H)，5.44(d，1H)，4.89(m，1H)。
19F?NMR(CDCl
3)δ：4.0(t，3F)，34.1(m，2F)，43.9(m，4F)，48.1(m，4F)。Embodiment 9
In a dry egg type bottle, add cholesterol chloro-formiate 200mg (0.45mmol), right-perfluoro hexyl thiophenol 180mg (0.42mmol), Tetramethyl Ethylene Diamine 0.1ml and methylene dichloride 10ml, 30 ℃ were reacted 50 hours down.The reaction solution washing, Na
2SO
4Dry back decompressing and extracting, column chromatography gets product 320mg, productive rate 90.6%.
MS(m/z)：368，427。
IR(KBr)υ(cm
-1)：1701。
1H?NMR(CDCl
3)δ：7.31(dd，4H)，5.43(d，1H)，4.91(m，1H)。
19F?NMR(CDCl
3)δ：3.79(t，3F)，32.96(m，2F)，44.18-44.60(m，4F)，45.69(m，2F)，
48.95(m，2F)。Embodiment 10
In a dry egg type bottle, add 24-and fall-5,22-cholestadienol 350mg (1.07mmol), right-(6-chlorine perfluoro hexyl) Benzoyl chloride 500mg (1.06mmol), triethylamine 0.25ml and 1,2-methylene dichloride 10ml, room temperature reaction 55 hours.The reaction solution washing, Na
2SO
4Dry back decompressing and extracting.Column chromatography gets product 760mg, productive rate 93.9%.
MS(m/z)：436，310。
IR(KBr)υ(cm
-1)：1721。
1H?NMR(CDCl
3)δ：8.20(d，2H)，7.69(d，2H)，5.67(m，1H)，5.37(d，1H)，4?86(m，
2H)，4.60(m，1H)。
19F?NMR(CDCl
3)δ：-9.3(t，2F)，34.5(m，2F)，44.8(m，4F)，45.9(m，2F)，
49.2(m，2F)。Embodiment 11
In a dry egg type bottle, add cholesterol 0.70g (1.81mmol), right-(6-hydrogen perfluoro butyl) phenylformic acid 0.58g (1.81mmol), DCC 0.50g (2.43mmol), DMAP 5mg and chlorobenzene 20ml, be heated to 100 ℃ of reactions 60 hours.The reaction solution decompressing and extracting.Column chromatography gets product 1.14g, productive rate 91.3%.
MS(m/z)：368，306。
IR(KBr)υ(cm
-1)：1722。
1H?NMR(CDCl
3)δ：8.20(d，2H)，7.67(d，2H)，5.44(d，1H)，4.93(m，1H)，
2.63(m，1H)。
19F?NMR(CDCl
3)δ：35.9(m，2F)，48.0(s，2F)，52.4(s，2F)，59.6(d，2F)。Embodiment 12
In a dry egg type bottle, add Dihydrocholesterol chloro-formic ester 250mg (0.55mmol), right-(4-chlorine perfluoro butyl) phenol 180mg (0.55mmol), pyridine 0.20ml and methylene dichloride 8ml, room temperature reaction 40 hours.The reaction solution washing, MgSO
4Dry back decompressing and extracting.Column chromatography gets product 370mg, productive rate 90.2%.
MS(m/z)：370。
IR(KBr)υ(cm
-1)：1755。
1H?NMR(CDCl
3)δ：7.36～7.69(dd，4H)，4.76(m，1H)。
19F?NMR(CDCl
3)δ：-9.0(m，2F)，36.8(m，2F)，43.7(s，2F)，46.2(s，2F)。Embodiment 13
In a dry egg type bottle, add cholesterol chloro-formiate 120mg (0.267mmol), right-(6-hydrogen perfluoro hexyl) thiophenol 100mg (0.244mmol), Tetramethyl Ethylene Diamine 0.15ml and methylene dichloride 6ml, room temperature reaction 60 hours.The reaction solution washing, Na
2SO
4Dry back decompressing and extracting.Column chromatography gets product 170mg, productive rate 84.8%.
MS(m/z)：368。
IR(KBr)υ(cm
-1)：1705.
1H?NMR(CDCl
3)δ：7.35(dd，4H)，5.42(d，1H)，4.88(m，1H)，2.64(m，1H)。
19F?NMR(CDCl
3)δ：34.9(m，2F)，44.8(m，4F)，45.8(m，2F)，49.5(m，2F)，
59.5(d，2F)。Embodiment 14
The transformation temperature of the fluorine-containing steroid liquid crystal of part and phase are measured with the polarized light microscopy method, and confirm that with dsc (DSC) the results are shown in the table, this class liquid crystal has ferroelectric phase-Sc
*Phase.Right-perfluoro hexyl cholesterol benzoate Cr 121.1 Sc
*134.7 S
A215.8 I211.0
S
A132.0 Sc
*(20.0 not crystallization) right-perfluoro capryl cholesterol benzoate Cr 135.2 Sc
*145.8 S
A220.1 I217.3
S
A142.8 Sc
*74.6 Cr is right-perfluoro hexyl phenylformic acid cholestane alcohol ester Cr 147.2 Sc
*175.9 Ch 176.7 I176.6
Ch 175.6 Sc
*144.4 Cr is right-perfluoro hexyl anilino formic acid cholesterol ester Cr 145.7 Sc 160.3 I154.6
S
A125.0 Cr is right-perfluoro capryl anilino formic acid cholesterol ester Cr 155.9 S
A186.6 I182.6
S
A136.7 Cr (right-perfluoro butyl) phenyl cholesteryl carbonic ether Cr 105.4 S
A112.0 Ch 117.7
I 119.45 Ch 109.8 S
A20 (not crystallization) (right-perfluoro hexyl) phenyl cholesteryl carbonic ether Cr, 100.3 S
A148.3 I146.5
S
A45.5 Sc
*-39 (not crystallization) (right-perfluoro capryl) phenyl cholesteryl carbonic ether Cr 122.4 SA 172.0 I169.8
S
A59.1 Sc
*-30 (not crystallization) (right-trifluoromethyl) phenyl cholesteryl carbonic ether Cr 126 I 117.4 Ch 76.4 Cr are the Cr-crystal wherein, I-isotropic liquid, Ch-cholesteryl phase, Sc
*-chiral smectic C phase, S
A-smectic A phase.
Claims (10)
1. ferroelectric type fluorine-containing steroid liquid crystal is characterized in that having following structural formula:
N=1-12 wherein, m=1 or 2, A=singly-bound, O, S, NH, CH
2CH
2Or CH=CH, B=singly-bound or S, D=5,6-dihydro or 5, the two keys of 6-, R=C
2-12Alkyl, thiazolinyl, alkyl acid methoxycarbonyl or ethoxycarbonyl, X=H, F or Cl.
2. ferroelectric type fluorine-containing steroid liquid crystal as claimed in claim 1 is characterized in that R is CH (CH in the described structure
3) CH
2CH
2CH
2CH (CH
3)
2, CH (CH
3) CH
2CH
2CO
2CH
3, CH (CH
3) CH
2CH
2CO
2C
2H
5, CH (CH
3) CH
2CH
2CH (C
2H
5) CH (CH
3)
2, CH (CH
3) CH=CHCH (CH
3) CH (CH
3)
2Or CH (CH
3) CH=CH
2
3. ferroelectric type fluorine-containing steroid liquid crystal as claimed in claim 1 or 2 is characterized in that having following structural formula:
N wherein, D, R, X is with claim 1.
4. ferroelectric type fluorine-containing steroid liquid crystal as claimed in claim 1 or 2 is characterized in that having following structural formula:
N wherein, D, R, X is with claim 1.
5. ferroelectric type fluorine-containing steroid liquid crystal as claimed in claim 1 or 2 is characterized in that having following structural formula:
N wherein, D, R, X is with claim 1.
6. ferroelectric type fluorine-containing steroid liquid crystal as claimed in claim 1 or 2 is characterized in that having following structural formula:
N wherein, D, R, X is with claim 1.
7. ferroelectric type fluorine-containing steroid liquid crystal as claimed in claim 1 or 2 is characterized in that having following structural formula:
N wherein, D, R, X is with claim 1.
8. ferroelectric type fluorine-containing steroid liquid crystal as claimed in claim 1 or 2 is characterized in that having following structural formula:
N wherein, D, R, X is with claim 1.
9. the preparation method of ferroelectric type steroid liquid crystal as claimed in claim 1 or 2 is characterized in that being made by following method respectively:
With the organic amine compound that has lone-pair electron on the nitrogen-atoms, mol ratio is 1: 0.7-2: 0.7-10, reacted 10-60 hour under the room temperature in solvent;
With the organic amine compound mol ratio that has lone-pair electron on the nitrogen-atoms be 1: 0.7-2: 0.7-10, in solvent under the room temperature reaction 10-60 hour;
Dewatering agent and catalyst molar ratio are 1: 0.8-5: 0.5-5: during 0-0.10, in the presence of solvent in room temperature to reflux temperature under the reaction 10-100 hour;
The organic amine compound that has lone-pair electron on the above-mentioned nitrogen-atoms is C
1-24Primary amine, secondary amine, tertiary amine, Tetramethyl Ethylene Diamine, tetraethyl-two quadrols, picoline, pyridine or bipyridine, described dewatering agent is N, N '-dicyclohexyl phosphinylidyne diimine, catalyzer is N, N-dimethyl amine pyridine, E=singly-bound, CH=CH or CH
2CH
2, described n, D, X or R are with claim 1.
10. the purposes of ferroelectric type fluorine-containing steroid liquid crystal as claimed in claim 1 or 2 is characterized in that being used for liquid crystal material.
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|---|---|---|---|
| CN 99113424 CN1229119A (en) | 1999-01-18 | 1999-01-18 | Ferroelectric type fluorine-containing steroid liquid crystal, preparation method and its use |
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|---|---|---|---|
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ID=5276614
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1111169C (en) * | 1999-12-24 | 2003-06-11 | 中国科学院上海有机化学研究所 | Sterol derivative, synthesis method and its application |
| CN1111167C (en) * | 1999-10-22 | 2003-06-11 | 中国科学院上海有机化学研究所 | 3 beta-hydroxy-5-cholenic acid ester derivant, synthesis process and use thereof |
-
1999
- 1999-01-18 CN CN 99113424 patent/CN1229119A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1111167C (en) * | 1999-10-22 | 2003-06-11 | 中国科学院上海有机化学研究所 | 3 beta-hydroxy-5-cholenic acid ester derivant, synthesis process and use thereof |
| CN1111169C (en) * | 1999-12-24 | 2003-06-11 | 中国科学院上海有机化学研究所 | Sterol derivative, synthesis method and its application |
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