JPH08157456A - Inonic liquid crystal compound - Google Patents
Inonic liquid crystal compoundInfo
- Publication number
- JPH08157456A JPH08157456A JP32922894A JP32922894A JPH08157456A JP H08157456 A JPH08157456 A JP H08157456A JP 32922894 A JP32922894 A JP 32922894A JP 32922894 A JP32922894 A JP 32922894A JP H08157456 A JPH08157456 A JP H08157456A
- Authority
- JP
- Japan
- Prior art keywords
- liquid crystal
- nitro
- crystal compound
- trans
- stilbazolium
- 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.)
- Pending
Links
Landscapes
- Pyridine Compounds (AREA)
- Liquid Crystal Substances (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明はスチルバゾリウム基を有
する新規なイオン性液晶化合物に関する。FIELD OF THE INVENTION The present invention relates to a novel ionic liquid crystal compound having a stilbazolium group.
【０００２】[0002]
【従来の技術】従来から新規な液晶化合物を開発すべく
多大な努力が重ねられている。本発明者等も新規な液晶
化合物を開発すべく鋭意検討した結果スチルバゾリウム
基を有する化合物が安定な液晶相を形成し得る液晶化合
物であることを見出すに至った。2. Description of the Related Art A great deal of effort has been made to develop new liquid crystal compounds. The inventors of the present invention have conducted extensive studies to develop a novel liquid crystal compound, and have found that a compound having a stilbazolium group is a liquid crystal compound capable of forming a stable liquid crystal phase.
【０００３】[0003]
【発明が解決しようとする課題】本発明の目的は新規な
液晶化合物を提供することである。An object of the present invention is to provide a novel liquid crystal compound.
【０００４】[0004]
【課題を解決するための手段】本発明によれば、下記一
般式（Ｉ）で表されるイオン性液晶化合物が提供され
る。 （式中のＲ１は炭素数が５〜２２の分岐を有していても
よいアルキル基を、Ｘは塩素又は臭素をそれぞれ表
す。）According to the present invention, there is provided an ionic liquid crystal compound represented by the following general formula (I). (R 1 in the formula represents an optionally branched alkyl group having 5 to 22 carbon atoms, and X represents chlorine or bromine, respectively.)
【０００５】[0005]
【好ましい実施態様】以下に好ましい実施態様を挙げて
本発明を説明する。本発明の液晶化合物は上記の一般式
（Ｉ）で表されるイオン性化合物であり、式中のＲ１は
炭素数が５〜２２の分岐を有していてもよいアルキル基
であり、Ｘは塩素又は臭素である。Ｘがいずれの場合も
アルキル基Ｒ1の炭素数に応じて種々の温度範囲におい
てスメクチック相を呈する。アルキル基Ｒ1の好ましい
炭素数は、Ｘが塩素の場合には５〜２２であり、Ｘが臭
素の場合には７〜２２である。BEST MODE FOR CARRYING OUT THE INVENTION The present invention will be described below with reference to preferred embodiments. The liquid crystal compound of the present invention is an ionic compound represented by the above general formula (I), wherein R 1 is an optionally branched alkyl group having 5 to 22 carbon atoms, and X Is chlorine or bromine. In any case of X, a smectic phase is exhibited in various temperature ranges depending on the carbon number of the alkyl group R 1 . The preferred carbon number of the alkyl group R 1 is 5 to 22 when X is chlorine, and 7 to 22 when X is bromine.
【０００６】本発明の液晶化合物は公知の方法によって
容易に合成することができるが、合成法の一例を次に示
す。 （１）トランス−４−ニトロ−スチルバゾールの合成 ４−ニトロ−ベンズアルデヒドと４−ピコロンを無水酢
酸の存在下に加熱反応させる。 （２）トランス−Ｎ−アルキル−４−ニトロ−４′−ス
チルバゾリウム クロライド又はブロマイドの合成 （１）の生成物と１−アルキルクロライド（又はブロマ
イド）をジメチルホルムアミド中で加熱下に反応させ
る。この際、種々の炭素数のアルキルハロライド（又は
ブロマイド）を用いることにより上記一般式（Ｉ）で表
されるイオン性液晶化合物が得られる。The liquid crystal compound of the present invention can be easily synthesized by a known method. An example of the synthetic method is shown below. (1) Synthesis of trans-4-nitro-stilbazole 4-nitro-benzaldehyde and 4-picolone are heated and reacted in the presence of acetic anhydride. (2) Synthesis of trans-N-alkyl-4-nitro-4'-stilbazolium chloride or bromide The product of (1) is reacted with 1-alkyl chloride (or bromide) in dimethylformamide under heating. At this time, an ionic liquid crystal compound represented by the above general formula (I) can be obtained by using an alkyl halide (or bromide) having various carbon numbers.
【０００７】[0007]
【実施例】以下に実施例により本発明を具体的に説明す
る。 製造例（トランス−Ｎ−ペンチル−４−ニトロ−４′−
スチルバゾリウム クロライドの合成） （１）４−ニトロ−ベンズアルデヒド１５．１ｇ（０．
１ｍｏｌ）と４−ピコリン１１．２ｇ（０．１２ｍｏ
ｌ）とを無水酢酸２０ｍｌ中で乾燥窒素ガス雰囲気下７
０℃で４８時間反応させた。反応終了後、冷却させた反
応混合物を冷水中に注ぎ、生成物を沈殿させ、フィルタ
ー濾過により生成物を回収した。生成物をクロロホルム
／メタノール（２０／１）を展開液としてシリカゲルカ
ラムを通し精製した。更に、精製物をメタノール溶液か
ら再結晶させた。収率は３８％であった。生成物の融点
は１７１．９℃（文献値１７１〜１７２℃）であり、
又、ＣＤＣｌ３を溶剤とする１Ｈ−ＮＭＲ分析の結果か
ら、生成物はトランス−４−ニトロ−スチルバゾールで
あることが確認された。EXAMPLES The present invention will be specifically described below with reference to examples. Production Example (trans-N-pentyl-4-nitro-4'-
(Synthesis of stilbazolium chloride) (1) 15.1 g of 4-nitro-benzaldehyde (0.
1 mol) and 4-picoline 11.2 g (0.12 mo)
l) and 7 in 20 ml of acetic anhydride under a dry nitrogen gas atmosphere.
The reaction was carried out at 0 ° C for 48 hours. After completion of the reaction, the cooled reaction mixture was poured into cold water to precipitate the product, and the product was collected by filtration with a filter. The product was purified by passing through a silica gel column using chloroform / methanol (20/1) as a developing solution. Further, the purified product was recrystallized from a methanol solution. The yield was 38%. The melting point of the product is 171.9 ° C. (literature values 171-172 ° C.),
In addition, the result of 1 H-NMR analysis using CDCl 3 as a solvent confirmed that the product was trans-4-nitro-stilbazole.
【０００８】（２）トランス−４−ニトロ−スチルバゾ
ール（２ｍｍｏｌ）と１−ペンチルクロライド（１０ｍ
ｍｏｌ）とをジメチルホルムアミド（ＤＭＦ）５ｍｌ中
で７０℃で７２時間反応させた。反応終了後、反応混合
物を冷却し、これを酢酸エチル５０ｍｌ中に注ぎ、生成
物を沈殿させ、沈澱物をフィルター濾過し、酢酸エチル
で洗浄した。生成物のクロロホルム溶液に酢酸エチルを
注ぎ生成物を再沈殿させて精製した。収率は１６％であ
った。ＵＶ分光分析及び１Ｈ−ＮＭＲ分析の結果、生成
物はトランス−Ｎ−ペンチル−４−ニトロ−４′−スチ
ルバゾリウム クロライドであることが確認された。
又、１−ペンチルクロライドを１−ペンチルブロマイド
に代えた以外は上記と同様にしてトランス−Ｎ−ペンチ
ル−４−ニトロ−４′−スチルバゾリウム ブロマイド
を得た。収率は９３％であった。(2) trans-4-nitro-stilbazole (2 mmol) and 1-pentyl chloride (10 m
was reacted with 5 ml of dimethylformamide (DMF) at 70 ° C. for 72 hours. After the reaction was completed, the reaction mixture was cooled, poured into 50 ml of ethyl acetate to precipitate the product, and the precipitate was filtered and washed with ethyl acetate. Ethyl acetate was poured into a chloroform solution of the product to reprecipitate the product for purification. The yield was 16%. As a result of UV spectroscopic analysis and 1 H-NMR analysis, it was confirmed that the product was trans-N-pentyl-4-nitro-4′-stilbazolium chloride.
Also, trans-N-pentyl-4-nitro-4'-stilbazolium bromide was obtained in the same manner as above except that 1-pentyl chloride was replaced with 1-pentyl bromide. The yield was 93%.
【０００９】実施例１ 上記の方法で合成したトランス−Ｎ−ペンチル−４−ニ
トロ−４′−スチルバゾリウム クロライド、トランス
−Ｎ−ペンチル−４−ニトロ−４′−スチルバゾリウム
ブロマイド及び上記方法に準じて合成した種々の炭素
数を有するトランス−Ｎ−アルキル−４−ニトロ−４′
−スチルバゾリウム クロライド及びブロマイドの相転
移温度をＤＳＣ（パーキンエルマー社製 ＤＳＣ７：昇
温及び冷却速度１０℃／分）により測定した。又、ホッ
トステージ（；コントロールユニット：ＭＥＴＴＬＥＲ
社製 ＦＰ８２ＨＴ）付きの偏光顕微鏡（オリンパス光
学社製 ＢＨＳ−７５１Ｐ）観察により相転移を確認し
た。相転移温度はこれらの化合物を室温から２５０℃ま
で昇温させてから室温迄冷却した後、再度昇温させなが
ら測定した。結果を表１に示す。尚、表１においては、
上記化合物をクロライドの場合をｎＣｌＳｚＮＯ２で、
ブロマイドの場合をｎＢｒＳｚＮＯ２で示す。ｎはアル
キル基の炭素数を示す。Example 1 Trans-N-pentyl-4-nitro-4'-stilbazolium chloride synthesized by the above method, trans-N-pentyl-4-nitro-4'-stilbazolium bromide and the above-mentioned method. -N-alkyl-4-nitro-4 'having various carbon numbers
The phase transition temperature of stilbazolium chloride and bromide was measured by DSC (DSC7 manufactured by Perkin Elmer Co., Ltd .: temperature rising and cooling rate 10 ° C./min). In addition, hot stage (; control unit: METLER
The phase transition was confirmed by observation with a polarizing microscope (BHS-751P manufactured by Olympus Optical Co., Ltd.) equipped with FP82HT manufactured by Co., Ltd. The phase transition temperature was measured by raising the temperature of these compounds from room temperature to 250 ° C., cooling to room temperature, and then raising the temperature again. The results are shown in Table 1. In addition, in Table 1,
When the above compound is chloride, nClSzNO 2 is used,
The case of bromide is indicated by nBrSzNO 2 . n represents the carbon number of the alkyl group.
【００１０】表１ Ｋ：結晶相 Ｓ：スメクチック相 Ｉ：アイソトロピック相Table 1 K: Crystalline phase S: Smectic phase I: Isotropic phase
【００１１】[0011]
【発明の効果】本発明の液晶化合物はイオン性を有する
液晶化合物であり、スメクチック相を誘起するからメモ
リー材料等として有用である。INDUSTRIAL APPLICABILITY The liquid crystal compound of the present invention is a liquid crystal compound having ionicity and induces a smectic phase, and is useful as a memory material or the like.
Claims (1)
晶化合物。 （式中のＲ１は炭素数が５〜２２の分岐を有していても
よいアルキル基を、Ｘは塩素又は臭素をそれぞれ表
す。）1. An ionic liquid crystal compound represented by the following general formula (I). (R 1 in the formula represents an optionally branched alkyl group having 5 to 22 carbon atoms, and X represents chlorine or bromine, respectively.)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32922894A JPH08157456A (en) | 1994-12-05 | 1994-12-05 | Inonic liquid crystal compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32922894A JPH08157456A (en) | 1994-12-05 | 1994-12-05 | Inonic liquid crystal compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08157456A true JPH08157456A (en) | 1996-06-18 |
Family
ID=18219089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP32922894A Pending JPH08157456A (en) | 1994-12-05 | 1994-12-05 | Inonic liquid crystal compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH08157456A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004065523A1 (en) * | 2003-01-24 | 2004-08-05 | Merck Patent Gmbh | Ionic mesogenic compounds |
-
1994
- 1994-12-05 JP JP32922894A patent/JPH08157456A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004065523A1 (en) * | 2003-01-24 | 2004-08-05 | Merck Patent Gmbh | Ionic mesogenic compounds |
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