CN1810924A - New liquid crystal compound in mesomorphic structure and its synthesis - Google Patents
New liquid crystal compound in mesomorphic structure and its synthesis Download PDFInfo
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- CN1810924A CN1810924A CNA2005100457982A CN200510045798A CN1810924A CN 1810924 A CN1810924 A CN 1810924A CN A2005100457982 A CNA2005100457982 A CN A2005100457982A CN 200510045798 A CN200510045798 A CN 200510045798A CN 1810924 A CN1810924 A CN 1810924A
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- trans
- cyclohexyl
- cholesteryl ester
- phenoxy group
- group
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- Liquid Crystal Substances (AREA)
Abstract
The present invention discloses one kind of liquid crystal compound in dimesoorphic structure and its preparing process, and the liquid crystal compound is synthesized with corresponding trans-alkylcyclohexyl phenol and cholesterol bromate through reaction in the presence of alkali through heating and stirring inside proper solvent, and contains both cyclohexyl phenol mesoorphic unit ad cholestene base mesoorphic unit. The general expression of the liquid crystal compound is shown. The liquid crystal compound has low and wide-range phase change temperature, simple cholestene phase and high physical and chemical stability, and may be used as liquid crystal material or liquid crystal material component.
Description
Technical field:
The present invention relates to a kind of liquid crystal compound in mesomorphic structure that contains cholesteryl and trans alkyl-cyclohexyl phenoxy group, and in the presence of alkali, adopt appropriate solvent to react by the bromo acid esters that corresponding alkyl replaces trans cyclohexylphenol and cholesterol and synthesize the preparation method who contains mesomorphic unit of trans alkyl-cyclohexyl phenyl and the mesomorphic unitary liquid crystal compound in mesomorphic structure of cholesteryl.
Background technology:
Liquid crystal compound in mesomorphic structure is meant and contains the compound that is connected two same mesomorphic structure unit (symmetry) or different mesomorphic structure unit (asymmetric) by the spacer of flexibility in the molecule.The liquid crystal compound in mesomorphic structure that contains Cholesteryl Group can form cholesteryl phase and causes extensive concern owing to containing the mesomorphic unit of chirality.Because its chiral additives that can be used as long pitch is doped to and makes it be converted into cholesteryl phase in the nematic liquid crystal, therefore significant with an inclined to one side doping agent that is used for liquid-crystal display to the exploitation novel liquid crystal, broad prospect of application is arranged in IT industry.
Done number of research projects for the liquid crystal compound in mesomorphic structure people that contain Cholesteryl Group, but it is higher to present complicated liquid crystal state and transformation temperature mostly, phase transformation range is narrower.(Marcelis?A?T?M，Koudijs?A，Sudholter?E?J?R.Odd-even?effects?in?thethermotropic?and?optical?properties?of?three?series?of?chiral?twin?liquidcrystals[J].Liq?Cryst，1995，18：843-850；Marcelis?A?T?M，Koudijs?A，Sudhlter?E?J?R.Dimer?liquid?crystals?with?bent?mesogenic?units[J].LiqCryst，2000，27(11)：1515-1523)；Lee?D?W，Jin?J?I.M.Laguerre.etal.Dimesogenic?compounds?swith?an?electron-attracting?terminal?group[J].Liq?Cryst，2000，27：145-152；Yelamaggad?C?V，Manoj?M.Unsymmetricaldimmers?possessing?a?cholesteryl?ester?moiety?and?a?difluoro-substitutedbiphenyl?core：synthesis?and?mesomorphic?behavior[J].Liq?Cryst，2003，30：125-133)。The material require low viscosity this and the time of response that are used for liquid-crystal display are closely related, will have good physical and chemical stability simultaneously.Trans phenylcyclohexane class liquid crystal and other as the phenol benzoate class, the biphenyl class, Schiff basess etc. have superior physical and chemical stability and lower viscosity.(Eidenschink?R.，Krause?J.，Pohl?L.，1978，US?Patent4130502)。
Summary of the invention:
The purpose of this invention is to provide a kind of liquid crystal compound in mesomorphic structure that contains cholesteryl and trans alkyl-cyclohexyl phenyl and preparation method thereof.This compounds has quite low transformation temperature and wide phase transformation range than corresponding benzoic acid cholesterol ester class liquid crystalline cpd, has good physics and chemical stability simultaneously.This compounds major part presents the liquid crystal state of single and low and wide cholesteryl phase, and part of compounds presents smectic A phase simultaneously.
Provided by the present invention is the compound of general formula (I):
R is the alkyl of 3-9 carbon atom in the formula, n=3-5,7
Specifically, the compound of general formula (I) is a kind of of following member:
4-(4-trans-(4-propyl group cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
01)
5-(4-trans-(4-propyl group cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
02)
6-(4-trans-(4-propyl group cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
03)
Sad cholesteryl ester (the I of 8-(4-trans-(4-propyl group cyclohexyl) phenoxy group)
04)
4-(4-trans-(4-butyl cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
05)
5-(4-trans-(4-butyl cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
06)
6-(4-trans-(4-butyl cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
07)
Sad cholesteryl ester (the I of 8-(4-trans-(4-butyl cyclohexyl) phenoxy group)
08)
4-(4-trans-(4-amyl group cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
09)
5-(4-trans-(4-amyl group cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
10)
6-(4-trans-(4-amyl group cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
11)
Sad cholesteryl ester (the I of 8-(4-trans-(4-amyl group cyclohexyl) phenoxy group)
12)
4-(4-trans-(4-hexyl cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
13)
5-(4-trans-(4-hexyl cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
14)
6-(4-trans-(4-hexyl cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
15)
Sad cholesteryl ester (the I of 8-(4-trans-(4-hexyl cyclohexyl) phenoxy group)
16)
4-(4-trans-(4-heptyl cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
17)
5-(4-trans-(4-heptyl cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
18)
6-(4-trans-(4-heptyl cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
19)
Sad cholesteryl ester (the I of 8-(4-trans-(4-heptyl cyclohexyl) phenoxy group)
20)
4-(4-trans-(4-octyl group cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
21)
5-(4-trans-(4-octyl group cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
22)
6-(4-trans-(4-octyl group cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
23)
Sad cholesteryl ester (the I of 8-(4-trans-(4-octyl group cyclohexyl) phenoxy group)
24)
4-(4-trans-(4-nonyl cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
25)
5-(4-trans-(4-nonyl cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
26)
6-(4-trans-(4-nonyl cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
27)
Sad cholesteryl ester (the I of 8-(4-trans-(4-nonyl cyclohexyl) phenoxy group)
28)
Second purpose of the present invention provides a kind of method for preparing general formula (I) compound.Be to realize this purpose, the present invention by the following technical solutions: bromo acid esters that will corresponding trans alkyl substituted cyclohexyl phenol and cholesterol adopts the appropriate solvent heated and stirred to react in the presence of alkali can have general formula (I) compound.Wherein alkyl contains 3-9 carbon atom, n=3-5,7.
Compound of the present invention has the lower transformation temperature and the phase transformation range of broad, has good physics and chemical stability simultaneously.This compounds major part presents the liquid crystal state of single and low and wide cholesteryl phase, and part of compounds presents smectic A phase simultaneously.Have broad application prospects at aspects such as liquid-crystal display and temperature sensing.
The present invention will be further described below in conjunction with specific embodiment.
Embodiment:
Embodiment 1:6-(4-trans (4-amyl group cyclohexyl) phenoxy group) caproic acid cholesteryl ester
In round-bottomed flask, add 4-trans (4-amyl group cyclohexyl) phenol (0.272g), 6-bromonexanoic acid cholesteryl ester (0.563g), Anhydrous potassium carbonate (0.138g), butanone (50ml) reflux 24 hours, filter, washing, dry, sherwood oil=1: 1), decompression desolventizes and obtain white solid 0.618g, productive rate 85% decompression desolventizes, silica gel column chromatography (eluent trichloromethane:.
1HNMR(CDCl3，300MHz)7.12(d，2H，J＝8.6Hz，Ar-
H)，6.82(d，2H，J＝8.6Hz，Ar-
H)，5.39(m，1H，olefinic)，4.61-4.64(m，1H，-OCH-)，3.95(t，2H，J＝6Hz，-OCH
2CH
2-)，2.41(t，1H，J＝10.5Hz，-H
a)，2.33(t，2H，J＝7.2Hz，-COCH
2CH
2-)，2.31-0.87(m，66H，-CH-，CH
2-，-CH
3)，0.69(s，3H，-CH
3).
FTIR(KBr，cm
-1)2926(aliphatic?C-H?stretching)，1737(C＝O?stretching)，1249?and1172(C-O?stretching).
MS：m/z?729[M+1]
+?calculated?for?C
50H
80O
3
DSC：Cr?21.4 N
*171.8
Same method can prepare Compound I
01-I
28
Claims (3)
1. require the patent protection compound to have the following general formula I structure:
R is the alkyl of 3-9 carbon atom in the formula, n=3-5,7
2. compound according to claim 1 is characterized in that: this compound is a kind of of following member:
4-(4-trans-(4-propyl group cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
01)
5-(4-trans-(4-propyl group cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
02)
6-(4-trans-(4-propyl group cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
03)
Sad cholesteryl ester (the I of 8-(4-trans-(4-propyl group cyclohexyl) phenoxy group)
04)
4-(4-trans-(4-butyl cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
05)
5-(4-trans-(4-butyl cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
06)
6-(4-trans-(4-butyl cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
07)
Sad cholesteryl ester (the I of 8-(4-trans-(4-butyl cyclohexyl) phenoxy group)
08)
4-(4-trans-(4-amyl group cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
09)
5-(4-trans-(4-amyl group cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
10)
6-(4-trans-(4-amyl group cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
11)
Sad cholesteryl ester (the I of 8-(4-trans-(4-amyl group cyclohexyl) phenoxy group)
12)
4-(4-trans-(4-hexyl cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
13)
5-(4-trans-(4-hexyl cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
14)
6-(4-trans-(4-hexyl cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
15)
Sad cholesteryl ester (the I of 8-(4-trans-(4-hexyl cyclohexyl) phenoxy group)
16)
4-(4-trans-(4-heptyl cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
17)
5-(4-trans-(4-heptyl cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
18)
6-(4-trans-(4-heptyl cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
19)
Sad cholesteryl ester (the I of 8-(4-trans-(4-heptyl cyclohexyl) phenoxy group)
20)
4-(4-trans-(4-octyl group cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
21)
5-(4-trans-(4-octyl group cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
22)
6-(4-trans-(4-octyl group cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
23)
Sad cholesteryl ester (the I of 8-(4-trans-(4-octyl group cyclohexyl) phenoxy group)
24)
4-(4-trans-(4-nonyl cyclohexyl) phenoxy group) butyric acid cholesteryl ester (I
25)
5-(4-trans-(4-nonyl cyclohexyl) phenoxy group) valeric acid cholesteryl ester (I
26)
6-(4-trans-(4-nonyl cyclohexyl) phenoxy group) caproic acid cholesteryl ester (I
27)
Sad cholesteryl ester (the I of 8-(4-trans-(4-nonyl cyclohexyl) phenoxy group)
28)
3. a method for preparing the described compound of claim 1 is that bromo acid esters with corresponding trans alkyl substituted cyclohexyl phenol and cholesterol adopts the reaction of appropriate solvent heated and stirred to obtain in the presence of alkali.Wherein R is the alkyl of 3-9 carbon atom, n=3-5,7.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2005100457982A CN1810924A (en) | 2005-01-28 | 2005-01-28 | New liquid crystal compound in mesomorphic structure and its synthesis |
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|---|---|---|---|
| CNA2005100457982A CN1810924A (en) | 2005-01-28 | 2005-01-28 | New liquid crystal compound in mesomorphic structure and its synthesis |
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|---|---|
| CN1810924A true CN1810924A (en) | 2006-08-02 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104159996A (en) * | 2012-03-07 | 2014-11-19 | 富士胶片株式会社 | Compound, liquid crystal composition, polymer material and film |
| CN104822800A (en) * | 2012-12-10 | 2015-08-05 | 默克专利股份有限公司 | BImesogenic compounds and mesogenic media |
| RU170758U1 (en) * | 2016-05-23 | 2017-05-05 | Федеральное государственное автономное научное учреждение "Центральный научно-исследовательский и опытно-конструкторский институт робототехники и технической кибернетики" (ЦНИИ РТК) | OBSTACLE TO MOBILE MECHANISM |
-
2005
- 2005-01-28 CN CNA2005100457982A patent/CN1810924A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104159996A (en) * | 2012-03-07 | 2014-11-19 | 富士胶片株式会社 | Compound, liquid crystal composition, polymer material and film |
| CN104159996B (en) * | 2012-03-07 | 2016-01-20 | 富士胶片株式会社 | Compound, liquid-crystal composition, macromolecular material and film |
| CN104822800A (en) * | 2012-12-10 | 2015-08-05 | 默克专利股份有限公司 | BImesogenic compounds and mesogenic media |
| RU170758U1 (en) * | 2016-05-23 | 2017-05-05 | Федеральное государственное автономное научное учреждение "Центральный научно-исследовательский и опытно-конструкторский институт робототехники и технической кибернетики" (ЦНИИ РТК) | OBSTACLE TO MOBILE MECHANISM |
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