JPH0759527B2 - Novel compound and liquid crystal composition containing the same - Google Patents
Novel compound and liquid crystal composition containing the sameInfo
- Publication number
- JPH0759527B2 JPH0759527B2 JP61266572A JP26657286A JPH0759527B2 JP H0759527 B2 JPH0759527 B2 JP H0759527B2 JP 61266572 A JP61266572 A JP 61266572A JP 26657286 A JP26657286 A JP 26657286A JP H0759527 B2 JPH0759527 B2 JP H0759527B2
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- compound
- temperature
- novel compound
- crystal composition
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims description 30
- 239000004973 liquid crystal related substance Substances 0.000 title description 25
- 239000000203 mixture Substances 0.000 title description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- -1 cyanophenyl ester Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 230000005526 G1 to G0 transition Effects 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- STBMZSJLFYGOJU-UHFFFAOYSA-N 1,1-dibromooctane Chemical compound CCCCCCCC(Br)Br STBMZSJLFYGOJU-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- QTBUMYNRHRINGJ-HZCBDIJESA-N C(CCCCCCC)OC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC Chemical compound C(CCCCCCC)OC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC QTBUMYNRHRINGJ-HZCBDIJESA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
Landscapes
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は、高温領域で使用可能な液晶材料あるいはガス
クロマトグラフィー固定相材料等に利用できる新規な化
合物に関する。TECHNICAL FIELD The present invention relates to a novel compound that can be used as a liquid crystal material or a gas chromatography stationary phase material that can be used in a high temperature range.
［従来の技術］ 現在、各種の液晶材料が提案されているが、その大半
は、中央部にリジットな基、例えば、ベンゼン環等の６
員環が１つか、又は、２つ直結、或いは、結合子を介し
て結合した基を有し、その両端、或いは一端にアルキル
基等のフレキシブルな基を有する化合物である。[Prior Art] Various liquid crystal materials have been proposed at present, most of which are rigid groups in the central part, such as benzene ring.
It is a compound having one or two member rings, a group directly bonded to each other, or a group bonded through a bond, and a flexible group such as an alkyl group at both ends or one end thereof.
ところが、最近、両端にリジットな基を有し、中央部に
フレキシブルな基を持つ液晶化合物が、ツイン（TWIN）
型液晶として注目されている。これらのツイン型液晶
は、液晶温度範囲が、広く高温で安定であり、形状効
果、例えば、フレキシブルな基の奇遇効果（炭素数が奇
数か偶数かによって液晶範囲温度が大幅に異なる現象
等）が大きいことが知られている。このような化合物と
して、両端にシアノビフェニル基 を有し、中央部に炭素数２〜10のアルキル鎖が酸素を介
して、いわゆるエーテル結合により化合したシアノビフ
ェニル系、同様に両端にシアノフェニルエステル基 を有したシアノフェニルエステル系、同様にシアノシッ
フ基 を有したシアノシッフ系、或いは、アルコキシシッフ基 を有したアルコキシシッフ系液晶化合物等が知られてい
る〔A.C.グリフィン（Griffin）他、モレキュラー、ク
リスタルス、アンド、リキッド、クリスタルス、レター
（Molecular Crystals and Liquid Crystals Lettars）
１巻５号131頁、或いはJ.I.ジン（Jin）他、モレキュラ
ー、クリスタルス、アンド、リキッド、クリスタルス
（Molecular Crystals and Li−quid Crystals）110巻2
93頁〕。However, recently, a liquid crystal compound that has a rigid group at both ends and a flexible group at the center has become twin (TWIN).
It is drawing attention as a type liquid crystal. These twin-type liquid crystals have a wide liquid crystal temperature range and are stable at high temperatures, and have a shape effect, for example, an odd effect of a flexible group (a phenomenon in which the liquid crystal range temperature greatly differs depending on whether the carbon number is an odd number or an even number). It is known to be great. As such a compound, a cyanobiphenyl group at both ends Cyanobiphenyl system in which an alkyl chain having 2 to 10 carbon atoms is compounded by oxygen bond in the central part through oxygen, so that cyanophenyl ester groups are similarly formed at both ends. A cyanophenyl ester system, also having a cyanoschiff group Cyano-schiff type or alkoxy-schiff group having Alkoxy Schiff-based liquid crystal compounds and the like are known [AC Griffin (Mriffin), Molecular, Crystals, And, Liquid, Crystals, Letter (Molecular Crystals and Liquid Crystals Lettars)
Vol. 1, No. 5, page 131, or JI Jin et al., Molecular Crystals and Li-quid Crystals 110 Vol. 2
Page 93].
［発明が解決しようとする問題点］ 上記化合物を液晶材料として用いる場合は、できるだけ
広い範囲で、液晶をとりうるものが好ましいが、一種の
化合物のみではそれを達成することが困難である。従っ
て、一般には、数種の化合物が混合して用いられるが、
上記性質を有するツイン型液晶として知られている化合
物は現在のところ非常に少ない。[Problems to be Solved by the Invention] When the above compound is used as a liquid crystal material, it is preferable that the compound can form a liquid crystal in a wide range as much as possible, but it is difficult to achieve it with only one compound. Therefore, generally, a mixture of several compounds is used,
At present, there are very few compounds known as twin type liquid crystals having the above properties.
本発明者は、かかる問題に鑑み、鋭意研究を進めた結
果、ツイン型液晶を採りうる新たな化合物を見い出し、
本発明に至ったものである。The present inventor, as a result of intensive studies in view of such problems, found a new compound that can adopt a twin type liquid crystal,
The present invention has been achieved.
すなわち、本発明の目的は、ツイン型液晶の性質を有す
る新規な化合物を提供することにある。That is, an object of the present invention is to provide a novel compound having twin type liquid crystal properties.
［問題点を解決するための手段］ 本発明は、下記式（Ｉ） Ｘ−Ｏ−（CH2）ｎ−Ｏ−Ｘ′ （Ｉ） （上記式中、Ｘ、Ｘ′は、 のいずれか、尚、ここでＲは炭素数２〜６のアルキル
基、又、上記ｎは、４〜10）で表される新規化合物、及
びこの新規化合物を含有することから成る液晶組成物で
ある。[Means for Solving Problems] The present invention provides the following formula (I) X—O— (CH 2 ) n— O—X ′ (I) (wherein X and X ′ are Wherein R is an alkyl group having 2 to 6 carbon atoms, the above n is 4 to 10), and a liquid crystal composition containing the novel compound. is there.
尚、上記記載中、 シクロヘキシル環を、 ベンゼン環を示す。In the above description, The cyclohexyl ring, Indicates a benzene ring.
上記式（Ｉ）の代表的化合物の例とその理化学的性質を
示すと次ぎのとおりである。Examples of typical compounds of the above formula (I) and their physicochemical properties are as follows.
α，ω−ビス｛ｐ−（トランス−４−ｎ−ブチルシクロ
ヘキシル）フェノキシ｝オクタン 1H−NMR（CDCl3,ppm）:7.1（ABq,4H）、6.8（ABq,4
H）、3.9（t,4H）、2.4（t,4H）0.9〜2.0（m,48H） この化合物は、偏光顕微鏡の観察下に加熱或いは冷却
すると次のような状態変化が生じる。加熱すると80℃の
温度で液晶相と成り、94℃の温度で大きめの粒々模様の
液晶相となり、100℃の温度でネマテイック相になり、1
24.5℃の温度で等方性液体となる。また、冷却すると、
123.6℃の温度でネマティック相となり、98℃の温度で
一瞬鮮やかなすじ模様がで、80℃の温度で模様が黒っぽ
くなり、69℃の温度で結晶化する。α, ω-bis {p- (trans-4-n-butylcyclohexyl) phenoxy} octane 1 H-NMR (CDCl 3 , ppm): 7.1 (ABq, 4H), 6.8 (ABq, 4
H), 3.9 (t, 4H), 2.4 (t, 4H) 0.9-2.0 (m, 48H) This compound undergoes the following state changes when heated or cooled under observation with a polarizing microscope. When heated, it becomes a liquid crystal phase at a temperature of 80 ° C, becomes a large grainy liquid crystal phase at a temperature of 94 ° C, and becomes a nematic phase at a temperature of 100 ° C.
It becomes an isotropic liquid at a temperature of 24.5 ° C. Also, when cooled,
It turns into a nematic phase at a temperature of 123.6 ° C, a bright streak pattern at a temperature of 98 ° C for a moment, turns dark at 80 ° C, and crystallizes at a temperature of 69 ° C.
α，ω−ビス（４′−ｎ−ブチルフェニルアゾ−４−フ
ェノキシ）オクタン 1H−NMR（CDCl3,ppm）:7.9（ABq,4H）、7.8（ABq,4
H）、7.3（ABq,4H）6.99（ABq,4H）、4.0（t,4H）、2.7
（t,4H）、1.1〜2.0（m,20H）、0.9（t,6H） この化合物は、偏光顕微鏡の観察下に加熱或いは冷却
すると次のような状態変化が生じる。加熱すると133.4
℃の温度で均一な液晶模様となり、135℃の温度でネマ
ティック相になり、流動性となり、169.1℃の温度で等
方性液体となる。また、冷却すると、168.7℃の温度で
ネマティック相となり、134℃の温度で模様にすじが入
り、暗くなる。132.5℃の温度で結晶化する。α, ω-bis (4'-n-butylphenylazo-4-phenoxy) octane 1 H-NMR (CDCl 3 , ppm): 7.9 (ABq, 4H), 7.8 (ABq, 4
H), 7.3 (ABq, 4H) 6.99 (ABq, 4H), 4.0 (t, 4H), 2.7
(T, 4H), 1.1 to 2.0 (m, 20H), 0.9 (t, 6H) This compound undergoes the following state changes when heated or cooled under observation with a polarizing microscope. 133.4 when heated
It becomes a uniform liquid crystal pattern at a temperature of ℃, becomes a nematic phase at a temperature of 135 ℃, becomes fluid, and becomes an isotropic liquid at a temperature of 169.1 ℃. Also, when cooled, it becomes a nematic phase at a temperature of 168.7 ° C, and streaks appear in the pattern at a temperature of 134 ° C, and it becomes dark. Crystallize at a temperature of 132.5 ° C.
上記例示化合物から、一般式（Ｉ）で示した化合物が液
晶化合物となり得ることは自明である。From the above exemplified compounds, it is obvious that the compound represented by the general formula (I) can be a liquid crystal compound.
尚、一般式（Ｉ）で示した化合物中のｎの数及びＲのア
ルキルの炭素鎖の長さは、その化合物が、液晶を取りう
る温度領域に影響を持つものであり、目的によって適宜
選定され得るもである。この化合物は、単独で用いるこ
とは勿論、他の液晶材料と混合して用いることができる
ことはいうまでもない。The number of n in the compound represented by the general formula (I) and the length of the alkyl carbon chain of R have an influence on the temperature range in which the compound can form a liquid crystal, and are appropriately selected depending on the purpose. It can also be done. It goes without saying that this compound can be used alone or as a mixture with another liquid crystal material.
上記式（Ｉ）の化合物は、 または と炭素数が４〜10のポリメチレンジハライドとをアルカ
リ金属化合物の存在下に反応させることによって得るこ
とができる。The compound of formula (I) above is Or And polymethylene dihalide having 4 to 10 carbon atoms in the presence of an alkali metal compound.
［実施例］ （実施例１） α，ω−ビス｛トランス−４−ｎ−ブチルシクロヘキシ
ル）フェノキシ｝オクタンの合成 ｐ−（トランス−４−ｎ−ブチルシクロヘキシル）フェ
ノール4.72g（20.4m mol）をシクロヘキサン100mlに溶
解し、無水炭酸ナトリウム14g（101.2m mol）及び1,8−
ジブロモオクタン2.72g（10m mol）を加え、18時間40分
還流した。冷却後、400mlの水を加えて振盪し、白色沈
殿物を別、水洗いした。この生成物を沸騰している酢
酸エチルエステル100mlに溶かして不溶分を除いた後、
再結晶させ、冷酢酸エチルエステル100mlで洗浄し、白
色針結晶4.41g（収率76.8％）を得た。この化合物は、
前述した理化学的性質を有していた。EXAMPLES Example 1 Synthesis of α, ω-bis {trans-4-n-butylcyclohexyl) phenoxy} octane p- (trans-4-n-butylcyclohexyl) phenol 4.72 g (20.4 mmol) Dissolved in 100 ml of cyclohexane, 14 g (101.2 mmol) of anhydrous sodium carbonate and 1,8-
2.72 g (10 mmol) of dibromooctane was added, and the mixture was refluxed for 18 hours and 40 minutes. After cooling, 400 ml of water was added and shaken, and a white precipitate was separated and washed with water. After dissolving this product in 100 ml of boiling ethyl acetate to remove the insoluble matter,
The crystals were recrystallized and washed with 100 ml of cold acetic acid ethyl ester to obtain 4.41 g (yield 76.8%) of white needle crystals. This compound is
It had the physicochemical properties described above.
（実施例２） α，ω−ビス（４′−ｎ−ブチルフェニルアゾ−４−フ
ェノキシ）オクタンの合成 ４′−ｎ−ブチルフェニルアゾ−４−フェノール5.2g
（20.4m mol）をシクロヘキサン100mlに溶解し、無水炭
酸ナトリウム14g（101.2m mol）及び1,8−ジブロモオク
タン2.72g（10m mol）を加え、17時間40分還流した。冷
却後、400mlの水を加えて振盪し、橙色沈殿物を別、
水洗いした。この生成物を沸騰している酢酸エチルエス
テル300mlに溶かして不溶分を除いた後、再結晶させ、
冷酢酸エチルエステル50mlで洗浄し、橙色結晶4.44g
（収率72％）を得た。この化合物は、前述した理化学的
性質を有していた。Example 2 Synthesis of α, ω-bis (4′-n-butylphenylazo-4-phenoxy) octane 4′-n-butylphenylazo-4-phenol 5.2 g
(20.4 mmol) was dissolved in 100 ml of cyclohexane, 14 g (101.2 mmol) of anhydrous sodium carbonate and 2.72 g (10 mmol) of 1,8-dibromooctane were added, and the mixture was refluxed for 17 hours and 40 minutes. After cooling, add 400 ml of water and shake to separate the orange precipitate,
I washed it with water. This product was dissolved in 300 ml of boiling ethyl acetate to remove the insoluble matter, and then recrystallized.
Wash with cold acetic acid ethyl ester 50ml, orange crystals 4.44g
(Yield 72%) was obtained. This compound had the physicochemical properties described above.
［発明の効果］ 本発明の化合物は、ツイン型液晶をとりうる新たな化合
物であり、高温領域で使用される液晶組成物の作成に際
し、液晶材料としての選択上の幅を広げ、また、ガスク
ロマトグラフィー固定相材料等に利用できる等格別の効
果を奏するものである。[Effects of the Invention] The compound of the present invention is a new compound capable of forming a twin type liquid crystal, and when the liquid crystal composition used in a high temperature region is prepared, the selection range as a liquid crystal material is widened, and a gas is used. It is particularly effective for chromatography stationary phase materials and the like.
───────────────────────────────────────────────────── フロントページの続き (56)参考文献 米国特許3883653（ＵＳ，Ａ) 英国特許749923（ＧＢ，Ａ) Ａｒｚｎｅｉｍｉｔｔｅｌ−Ｆｏｒｓｃ ｈｕｎｇ，35〔７〕（1985）ｐ．1009− 1014 Ｊｏｕｒｎａｌ ｏｆ Ｍｅｄｉｃｉｎ ａｌ Ｃｈｅｍｉｓｔｒｙ，16〔９〕 （1973）ｐ．970−975 Ｂｕｌｌｅｔｉｎ ｄｅ ｌａ Ｓｏｃ ｉｅｔｅ Ｃｈｉｍｉｇｎｅ ｄｅ Ｆｒ ａｎｃｅ，〔12〕（1964）ｐ．3155−3158 ─────────────────────────────────────────────────── --Continued Front Page (56) References US Patent 3883853 (US, A) UK Patent 749923 (GB, A) Arzneimitel-Forsc hung, 35 [7] (1985) p. 1009-1014 Journal of Medicinal Chemistry, 16 [9] (1973) p. 970-975 Bulletin de la Societe Chimigne de France, [12] (1964) p. 3155-3158
Claims (2)
基、また、上記ｎは、４〜10）で表される新規化合物。1. The following formula (I) X—O— (CH 2 ) n— O—X ′ (I) (wherein X and X ′ are: Any of the above, wherein R is an alkyl group having 2 to 6 carbon atoms, and the above n is a novel compound represented by 4 to 10).
基、また、上記ｎは、４〜10）で表される化合物を含有
することを特徴とする液晶組成物。2. The following formula (I) X—O— (CH 2 ) n— O—X ′ (I) (wherein X and X ′ are: Any one of the above, wherein R is an alkyl group having 2 to 6 carbon atoms, and the above n is a compound represented by 4 to 10).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61266572A JPH0759527B2 (en) | 1986-11-11 | 1986-11-11 | Novel compound and liquid crystal composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61266572A JPH0759527B2 (en) | 1986-11-11 | 1986-11-11 | Novel compound and liquid crystal composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63122640A JPS63122640A (en) | 1988-05-26 |
| JPH0759527B2 true JPH0759527B2 (en) | 1995-06-28 |
Family
ID=17432677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61266572A Expired - Lifetime JPH0759527B2 (en) | 1986-11-11 | 1986-11-11 | Novel compound and liquid crystal composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0759527B2 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB749923A (en) | 1953-01-14 | 1956-06-06 | Wellcome Found | Bis-(ú-aminophenoxy) alkanes |
| US3883653A (en) | 1972-10-24 | 1975-05-13 | Pfizer | Method of preventing asthmatic symptoms |
-
1986
- 1986-11-11 JP JP61266572A patent/JPH0759527B2/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB749923A (en) | 1953-01-14 | 1956-06-06 | Wellcome Found | Bis-(ú-aminophenoxy) alkanes |
| US3883653A (en) | 1972-10-24 | 1975-05-13 | Pfizer | Method of preventing asthmatic symptoms |
Non-Patent Citations (3)
| Title |
|---|
| Ａｒｚｎｅｉｍｉｔｔｅｌ−Ｆｏｒｓｃｈｕｎｇ，３５〔７〕（１９８５）ｐ．１００９−１０１４ |
| ＢｕｌｌｅｔｉｎｄｅｌａＳｏｃｉｅｔｅＣｈｉｍｉｇｎｅｄｅＦｒａｎｃｅ，〔１２〕（１９６４）ｐ．３１５５−３１５８ |
| ＪｏｕｒｎａｌｏｆＭｅｄｉｃｉｎａｌＣｈｅｍｉｓｔｒｙ，１６〔９〕（１９７３）ｐ．９７０−９７５ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS63122640A (en) | 1988-05-26 |
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