JPH01180858A - Optically active biphenyl ester compound - Google Patents
Optically active biphenyl ester compoundInfo
- Publication number
- JPH01180858A JPH01180858A JP222688A JP222688A JPH01180858A JP H01180858 A JPH01180858 A JP H01180858A JP 222688 A JP222688 A JP 222688A JP 222688 A JP222688 A JP 222688A JP H01180858 A JPH01180858 A JP H01180858A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- compound
- acid
- chlorine
- liquid crystal
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 biphenyl ester compound Chemical class 0.000 title claims abstract description 14
- 235000010290 biphenyl Nutrition 0.000 title claims abstract description 6
- 239000004305 biphenyl Substances 0.000 title claims abstract description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 5
- 239000005262 ferroelectric liquid crystals (FLCs) Substances 0.000 abstract description 5
- 230000010287 polarization Effects 0.000 abstract description 4
- 230000002269 spontaneous effect Effects 0.000 abstract description 4
- 239000004990 Smectic liquid crystal Substances 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 6
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 210000002858 crystal cell Anatomy 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
- NVAYQEDPGCVWSF-UHFFFAOYSA-N 2-(2-hydroxyphenyl)-4-octoxyphenol Chemical compound CCCCCCCCOC1=CC=C(O)C(C=2C(=CC=CC=2)O)=C1 NVAYQEDPGCVWSF-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 1
- BVLVGYXYGXOSOG-UHFFFAOYSA-N 2-hexoxybenzoic acid Chemical compound CCCCCCOC1=CC=CC=C1C(O)=O BVLVGYXYGXOSOG-UHFFFAOYSA-N 0.000 description 1
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 1
- AZYTZQYCOBXDGY-UHFFFAOYSA-N 2-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=CC=N1 AZYTZQYCOBXDGY-UHFFFAOYSA-N 0.000 description 1
- IONOBWJYMNPSLH-GICMACPYSA-N 4-[(4R)-6-chloro-4-methyldecoxy]phenol Chemical compound CCCCC(Cl)C[C@H](C)CCCOC1=CC=C(O)C=C1 IONOBWJYMNPSLH-GICMACPYSA-N 0.000 description 1
- IEKOCLQHTNIIGH-UHFFFAOYSA-N 5-octoxy-2-phenylbenzoic acid Chemical compound OC(=O)C1=CC(OCCCCCCCC)=CC=C1C1=CC=CC=C1 IEKOCLQHTNIIGH-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は強誘電性液晶化合物として有用な光学活性ビフ
ェニルエステル化合物に関し、詳しくは、含塩素アルコ
キシ基を有する光学活性ビフェニルエステル化合物に関
する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an optically active biphenyl ester compound useful as a ferroelectric liquid crystal compound, and more particularly to an optically active biphenyl ester compound having a chlorine-containing alkoxy group.
不斉炭素原子を有するアルコキシヘンゼン誘導体は液晶
化学物質用中間体として近年特に注目を集めており、特
に、アルコキシビフェニル化合物、アルコキシフェニル
ピリミジン化合物、アルコキシ安息香酸誘導体等は強誘
電性スメクチック液晶化学物質として知られている。Alkoxyhensen derivatives having asymmetric carbon atoms have attracted particular attention in recent years as intermediates for liquid crystal chemicals, and in particular, alkoxybiphenyl compounds, alkoxyphenylpyrimidine compounds, alkoxybenzoic acid derivatives, etc. are used as ferroelectric smectic liquid crystal chemicals. known as.
これらの液晶化合物におけるアルコキシ基としては、６
−メチルオクトキシ基、２−メチルブトキシ基等が知ら
れているが、これらの化合物は使用可能温度範囲が適切
でなかったり、あるいは配向安定性が劣ったりする問題
を有しており、実用的なものではなかった。The alkoxy group in these liquid crystal compounds is 6
-Methyloctoxy group, 2-methylbutoxy group, etc. are known, but these compounds have problems such as an inappropriate usable temperature range or poor orientation stability, making them impractical. It wasn't something.
このため、化合物の基本骨格を含め、現在強誘電性液晶
化合物について種々の検討が続けられていた。For this reason, various studies have been ongoing regarding ferroelectric liquid crystal compounds, including the basic skeleton of the compound.
本発明者等は、不斉炭素原子を有するアルコキシビフェ
ニル化合物について鋭意検討を重ねた結果、次の一般式
で表される化合物が優れた液晶性を有していることを見
出した。As a result of intensive studies on alkoxybiphenyl compounds having an asymmetric carbon atom, the present inventors found that a compound represented by the following general formula has excellent liquid crystallinity.
（式中、Ｒは炭素原子数１ないし１８の直鎖アルキル基
を示し、Ｒ゛は塩素含有アルキル基を示し、Ｘは−ＣＯ
−０−または一〇−ＣＯ−を示し、ｐおよびｑはそれぞ
れＯまたは１を示し、ｐ＋ｑ＝１を示し、ｎは２〜５を
示し、＊は不斉炭素原子を示す。）上記−最大で示され
る化合物において、Ｒ”で示される塩素含有アルキル基
としては、２−クロロエチル、３−クロロプロピル、２
−クロロプロピル、２−クロロブチル、３−クロロペン
チル、２−クロロオクチル、３−クロロデシル、２−ク
ロロドテシル等の基があげられる。(In the formula, R represents a straight-chain alkyl group having 1 to 18 carbon atoms, R' represents a chlorine-containing alkyl group, and X represents -CO
-0- or 10-CO-, p and q each represent O or 1, p+q=1, n represents 2 to 5, and * represents an asymmetric carbon atom. ) In the compounds shown above - maximum, the chlorine-containing alkyl group represented by R'' includes 2-chloroethyl, 3-chloropropyl, 2-chloropropyl,
Examples thereof include groups such as -chloropropyl, 2-chlorobutyl, 3-chloropentyl, 2-chlorooctyl, 3-chlorodecyl, and 2-chlorodotecyl.
上記−最大で表される化合物は、例えば、アルコキシビ
フェニルカルボン酸と光学活性な含塩素アルコキシフェ
ノールとを反応させるか、あるいは光学活性な含塩素ア
ルコキシ安息香酸とアルコキシビフェノールとを脱水剤
の存在下に反応させることにより容易に製造することが
できる。The compound represented by the maximum above can be obtained by, for example, reacting an alkoxybiphenylcarboxylic acid with an optically active chlorine-containing alkoxyphenol, or reacting an optically active chlorine-containing alkoxybenzoic acid with an alkoxybiphenol in the presence of a dehydrating agent. It can be easily produced by reaction.
次に、本発明を実施例によって説明する。Next, the present invention will be explained by examples.
実施例 １
０．６５ｇの４−ｎ−オクチルオキシビフェニルカルボ
ン酸、０．６０ｇの（Ｒ）−４〜（６゛−クロロ−４゛
−メチルデシルオキシ）フェノール、０．０４ｇのＮ、
Ｎ’−ジシクロへキシルカルボジイミド及び０．０４ｇ
の４−ピロリジノピリジンをジクロルメタン２０１ｄに
加え、室温で３時間反応した。析出したジシクロヘキシ
ル尿素をろ別後、ろ液を脱溶媒した。得られた粗生成物
をエタノール／アセトン（７／３）混合溶媒から再結晶
を繰り返して、目的の（Ｒ）−４−ｎ−オクチルオキシ
ビフェニルカルボン酸−４−（６”−クロロ−４゛−メ
チルデシルオキシ）フェニルエステルを得た。Example 1 0.65 g of 4-n-octyloxybiphenylcarboxylic acid, 0.60 g of (R)-4-(6'-chloro-4'-methyldecyloxy)phenol, 0.04 g of N,
N'-dicyclohexylcarbodiimide and 0.04g
4-pyrrolidinopyridine was added to dichloromethane 201d and reacted at room temperature for 3 hours. After separating the precipitated dicyclohexylurea by filtration, the filtrate was desolvented. The obtained crude product was repeatedly recrystallized from a mixed solvent of ethanol/acetone (7/3) to obtain the desired (R)-4-n-octyloxybiphenylcarboxylic acid-4-(6''-chloro-4゛). -methyldecyloxy)phenyl ester was obtained.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
３０８０ｃｍ−’ （ｖｗ）、２９５０ｃｍ−’ （
ｓ）、２８８０ｃｍ−’ （ｍ）、１７３５ｃｍ−’
（ｓ）、１６１０ｃｍ−’ （ｓ）、１５８５ｃ
ｍ−’（ｖｗ）、１５１０ｃｍ−’ （ｓ）、１４７
０ｃｍ−’ （ｍ）、１４００ｃｎ＋−’ （ｗ）
、１２８０ｃｍ−’ （ｓ）、１２５０ｃｍ−’
（ｓ）、１２００ｃｍ−’ （ｓ）、１０８５ｃｍ’
−’ （ｓ）、１０４１０４Ｏ’ （ｗ）、１０２
１０２Ｏ’ （ｗ）、８７５ｃｍ”’ （ｗ）、
８３５ｃｍ ’ （ｍ）、 ７７０ｃｍ−’ （
ｍ）、７２５ｃｍ−’ （ｗ）、 ７００ｃｍ−’
（ｗ） ５３０ｃｍ−’ 軸）この化合物を二
枚のガラス板に挟み、偏光顕微鏡による相形態観察を行
った結果、以下の相転移を確認した。3080cm-' (vw), 2950cm-' (
s), 2880cm-' (m), 1735cm-'
(s), 1610cm-' (s), 1585c
m-' (vw), 1510 cm-' (s), 147
0cm-' (m), 1400cn+-' (w)
, 1280cm-' (s), 1250cm-'
(s), 1200cm-' (s), 1085cm'
-' (s), 104104O' (w), 102
102O' (w), 875cm'' (w),
835cm' (m), 770cm-' (
m), 725cm-' (w), 700cm-'
(w) 530 cm-' axis) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
この化合物を、ラビングにより配向処理を施した厚さ２
μｍのガラス透明電極セルに注入した後に、１８０″Ｃ
に加熱して等方性液体とした。この液晶セルを１５０°
Ｃまで徐冷し、直交ニコル下で±１５Ｖ、ＩＨｚの短形
波を印加したところ、明瞭なスイッチング動作が確認さ
れた。また三角波法を用いて自発分極を測定したところ
、１．７ ｎＣ／ｃＩ１１２であった。また１１０℃で
の応答速度（電界印加から９０％立ち上がりまでの時間
）は２００μｓｅｃであった・
実施例 ２
０．３５ｇの（Ｒ）−４−（６’−クロロ−３°−メチ
ルへキシルオキシ）ビフェニルカルボン酸、０．２５ｇ
の４−〇−デシルオキシフェノール、０．２１ｇのＮ、
Ｎ’−ジシクロへキシルカルボジイミドおよび０．０
２ｇの４−ピロリジノピリジンをジクロルメタン１０Ｉ
Ｒ１に加え、実施例１と同様の操作を行った。得られた
粗生成物をヘキサン／ジクロルメタン（１／１）を展開
溶媒としてシリカゲルカラムを用いて精製し、目的の（
Ｒ）−４−（６’−クロロ−３゛−メチルヘキシルオキ
シ
シフェニルエステルを得た。This compound was oriented by rubbing to a thickness of 2.
After injection into μm glass transparent electrode cell, 180″C
It was heated to an isotropic liquid. This liquid crystal cell is 150°
After cooling slowly to C, a rectangular wave of ±15 V and IHz was applied under crossed nicols, and a clear switching operation was confirmed. Further, when the spontaneous polarization was measured using the triangular wave method, it was found to be 1.7 nC/cI112. In addition, the response speed (time from application of electric field to 90% rise) at 110°C was 200 μsec. Example 2 0.35 g of (R)-4-(6'-chloro-3°-methylhexyloxy) Biphenylcarboxylic acid, 0.25g
of 4-0-decyloxyphenol, 0.21 g of N,
N'-dicyclohexylcarbodiimide and 0.0
2g of 4-pyrrolidinopyridine in dichloromethane 10I
In addition to R1, the same operations as in Example 1 were performed. The obtained crude product was purified using a silica gel column using hexane/dichloromethane (1/1) as a developing solvent to obtain the desired (
R)-4-(6'-chloro-3'-methylhexyloxycyphenyl ester was obtained.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
３０８０ｃｍ−’ （ｖｗ）、２９５０ｃｍ−’ （ｓ
）、２８８０ｃｍ−’ （ｍ）、１７４０ｃｍ”’ （
ｓ）、１６１０ｃｍ−’ （ｍ）、１５８５ｃｍ−’
（ｖｗ）、１５１５ｃｍ−’ （ｓ）、１４８０ｃｍ−
’ （ｍ）、１４００ｃｍ−’ （ｗ）、１３００ｃｍ
−’ （ｓ）、１２６０ｃｍ−’ （ｓ）、１２１５ｃ
ｍ−’ （ｓ）、１０９１０９Ｏ’ （ｍ）、１０３５
ｃｍ−’ （ｗ）、８８０ｃｍ−’ （ｗ）、８３５ｃ
ｍ−’ （ｍ）、７７５ｃｍ−’ （ｍ）、７２５ｃｍ
−’ （ｗ）、７００ｃｍ−’ （ｗ）、５３０ｃｍ−
’ （ｗ）この化合物を二枚のガラス板間に挟み、偏光
顕微鏡による相形態観察を行った結果、以下の相転移を
確認した。3080cm-' (vw), 2950cm-' (s
), 2880cm-' (m), 1740cm"' (
s), 1610cm-' (m), 1585cm-'
(vw), 1515cm-' (s), 1480cm-
' (m), 1400cm-' (w), 1300cm
-' (s), 1260cm-' (s), 1215c
m-' (s), 109109O' (m), 1035
cm-' (w), 880cm-' (w), 835c
m-' (m), 775cm-' (m), 725cm
-' (w), 700cm-' (w), 530cm-
(w) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
実施例 ３
０．６０ｇの（Ｒ） −４−（６’−クロロ−４“−メ
チルオクチルオキシ）安息香酸、０．６０ｇの４−ｎ−
オクチルオキシビフェノール、０．４１ｇのＮ、Ｎ”−
ジシクロヘキシルカルボジイミドおよび０．０４ｇの４
−ピロリジノピリジンをジクロルメタン２０ｄに加え、
実施例１と同様の操作を行い、目的の（Ｒ）−４−（６
”−クロロ−４゛−メチルオキシノ安息香酸−４−ｎ−
オクチルオキシビフェニルエステルを得た。Example 3 0.60 g of (R)-4-(6'-chloro-4"-methyloctyloxy)benzoic acid, 0.60 g of 4-n-
Octyloxybiphenol, 0.41g N,N”-
dicyclohexylcarbodiimide and 0.04 g of 4
- add pyrrolidinopyridine to 20d dichloromethane,
The same operation as in Example 1 was performed to obtain the desired (R)-4-(6
"-Chloro-4'-methyloxynobenzoic acid-4-n-
Octyloxybiphenyl ester was obtained.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
３０６０ｃｍ−’ （ｖｗ）、２９５０ｃｍ−’ （ｓ
）、２８７５ｃ＋ａ−’ （ｍ）、１７３０ｃｍ−’
（ｓ）、１６１０ｃｍ−’ （ｓ）、１５８０ｃｍ−’
（ｗ）、１５１０ｃｍ−’ （ｍ）、１５００ｃｍ
−’ 軸）、１４７０ｃｍ−’ （ｍ）、１４２５
ｃｍ−’ （ｗ）、１３８５ｃｍ−’ （ｗ）、１２６
０ｃｍ−’ （ｓ）、１２１５ｃｍ−’ （ｓ）、１１
７５ｃｍ−’ （ｓ）、１０８１０８Ｏ’ （ｍ）、１
００１０Ｏ５’ （ｗ）、９７０ｃｍ−’ （ｗ）、８
９０ｃｍ−’ （ｗ）、８５０ｃｍ−’ （ｍ）、８
１０ｃｍ−’ 軸）、 ７７０ｃｍ−’ （ｍ）、
７００ｃｍ−’ （ｗ）、６５５ｃｍ−’ （ｗ）
５２０ｃｍ−’ （ｗ）この化合物を二枚のガラス板間
に挟み、偏光顕微鏡による相形態観察を行った結果、以
下の相転移を確認した。3060cm-' (vw), 2950cm-' (s
), 2875c+a-' (m), 1730cm-'
(s), 1610cm-' (s), 1580cm-'
(w), 1510cm-' (m), 1500cm
-' axis), 1470cm-' (m), 1425
cm-' (w), 1385 cm-' (w), 126
0cm-' (s), 1215cm-' (s), 11
75cm-' (s), 108108O' (m), 1
0010O5' (w), 970cm-' (w), 8
90cm-' (w), 850cm-' (m), 8
10cm-' axis), 770cm-' (m),
700cm-' (w), 655cm-' (w)
520 cm-' (w) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
この化合物を、ラビングにより配向処理を施した厚さ２
μｍのガラス透明電極セルに注入した後に、１８０°Ｃ
に加熱して等方性液体とした。この液晶セルを１００°
Ｃまで徐冷し、直交ニコル下で±１５Ｖ、ＩＨｚの短形
波を印加したところ、明瞭なスイッチング動作が確認さ
れた。その時の応答速度は３５０μｓｅｃであった。三
角波法を用いて自発分極を測定したところ、１２．８
ｎＣ／ｃｍ”であった。This compound was oriented by rubbing to a thickness of 2.
180°C after injection into a μm glass transparent electrode cell.
It was heated to an isotropic liquid. This liquid crystal cell is 100°
After cooling slowly to C, a rectangular wave of ±15 V and IHz was applied under crossed nicols, and a clear switching operation was confirmed. The response speed at that time was 350 μsec. When the spontaneous polarization was measured using the triangular wave method, it was found to be 12.8.
nC/cm".
実施例 ４
０．４４ｇのｎ−ヘキシルオキシ安息香酸、０．６４ｇ
の（Ｒ）−４−（６’−り四ロー４゛−メチルへキシル
オキシ）ビフェノール、０．４１ｇのＮ、Ｎ”−ジシク
ロヘキシルシルポジイミドおよび０．０４ｇの４−ピロ
リジノピリジンをジクロルメタン２０戚に加え、実施例
１と全く同様の操作を行い、目的の（Ｒ）−４−ｎ−ヘ
キシルオキシ安息香酸−４−（６’−クロロ−４′−メ
チルへキシルオキシ）ビフェニルエステルを得た。Example 4 0.44g n-hexyloxybenzoic acid, 0.64g
of (R)-4-(6'-ly-4'-methylhexyloxy)biphenol, 0.41 g of N,N"-dicyclohexylsilposiimide and 0.04 g of 4-pyrrolidinopyridine in dichloromethane 20. In addition, the same operation as in Example 1 was performed to obtain the target (R)-4-n-hexyloxybenzoic acid-4-(6'-chloro-4'-methylhexyloxy)biphenyl ester.
赤外分光分析の結果、得られた生成物は次の特性吸収を
有しており、目的物であることを確認した。As a result of infrared spectroscopic analysis, the obtained product had the following characteristic absorption, and was confirmed to be the desired product.
３０６０ｃｍ−’ （ｖｉｙ）、２９５０ｃｍ−’ （
ｍ）、２８９０ｃｍ−’ （ｗ）、１７３０ｃｍ−’
（ｓ）、１６１０ｃｍ−’ （ｓ）、１５８０ｃｍ−’
（ｗ）、１５００ｃｍ−’ （ｓ）、１４７０ｃｍ−
’ （ｍ）、１４２５ｃｍ−’ （ｗ）、１３９０ｃｍ
−’ （ｗ）、１２６０ｃｍ−’ （ｓ）、１２１５ｃ
ｍ−’ （ｓ）、１１７５ｃｍ−’ （ｓ）、１０８１
０８Ｏ’ （ｍ）、１００１０Ｏ５’ （ｍ）、９４０
ｃｍ−’ （ｗ＞、８８５ｃｍ−’ （ｗ）、８５０ｃ
ｍ−’ （ｍ）、８１５ｃｍ−’ （ｍ）、７７０ｃｍ
−’ （ｍ）、７００ｃｍ−’ （ｗ）、６５５ｃｒ’
（ｍ）、５２０ｃｍ−’ （ｗ）この化合物を二枚の
ガラス板間に挟み、偏光顕微鏡による相形態観察を行っ
た結果、以下の相転移を確認した。3060cm-' (viy), 2950cm-' (
m), 2890cm-' (w), 1730cm-'
(s), 1610cm-' (s), 1580cm-'
(w), 1500cm-' (s), 1470cm-
' (m), 1425cm-' (w), 1390cm
-' (w), 1260cm-' (s), 1215c
m-' (s), 1175 cm-' (s), 1081
08O' (m), 10010O5' (m), 940
cm-'(w>,885cm-' (w), 850c
m-' (m), 815cm-' (m), 770cm
-' (m), 700cm-' (w), 655cr'
(m), 520 cm-' (w) This compound was sandwiched between two glass plates, and the phase morphology was observed using a polarizing microscope. As a result, the following phase transition was confirmed.
これらの化合物群は、高温で広いスメクチ、７り相を示
し、ＳｍＣ”相の自発分極は大きいので強誘電性液晶の
一成分として用いるのに適している。These compound groups exhibit wide smectic and heptagonal phases at high temperatures, and the spontaneous polarization of the SmC'' phase is large, making them suitable for use as a component of ferroelectric liquid crystals.
Claims (1)
物。 ▲数式、化学式、表等があります▼ （式中、Ｒは炭素原子数１ないし１８の直鎖アルキル基
を示し、Ｒ’は塩素含有アルキル基を示し、Ｘは−ＣＯ
−Ｏ−または−Ｏ−ＣＯ−を示し、ｐおよびｑはそれぞ
れ０または１を示し、ｐ＋ｑ＝１を示し、ｎは２〜５を
示し、＊は不斉炭素原子を示す。）[Claims] An optically active biphenyl ester compound represented by the following general formula. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (In the formula, R represents a straight-chain alkyl group having 1 to 18 carbon atoms, R' represents a chlorine-containing alkyl group, and X represents -CO
-O- or -O-CO-, p and q each represent 0 or 1, p+q=1, n represents 2 to 5, and * represents an asymmetric carbon atom. )
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP222688A JPH0830037B2 (en) | 1988-01-08 | 1988-01-08 | Optically active biphenyl ester compound |
| US07/242,177 US4959173A (en) | 1987-09-29 | 1988-09-08 | Optically active ester compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP222688A JPH0830037B2 (en) | 1988-01-08 | 1988-01-08 | Optically active biphenyl ester compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01180858A true JPH01180858A (en) | 1989-07-18 |
| JPH0830037B2 JPH0830037B2 (en) | 1996-03-27 |
Family
ID=11523442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP222688A Expired - Lifetime JPH0830037B2 (en) | 1987-09-29 | 1988-01-08 | Optically active biphenyl ester compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0830037B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009117387A (en) * | 2009-02-23 | 2009-05-28 | Railway Technical Res Inst | Conductive structure |
-
1988
- 1988-01-08 JP JP222688A patent/JPH0830037B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009117387A (en) * | 2009-02-23 | 2009-05-28 | Railway Technical Res Inst | Conductive structure |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0830037B2 (en) | 1996-03-27 |
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