JPH0262874A - Benzothiopyrylium-based compound - Google Patents
Benzothiopyrylium-based compoundInfo
- Publication number
- JPH0262874A JPH0262874A JP21165788A JP21165788A JPH0262874A JP H0262874 A JPH0262874 A JP H0262874A JP 21165788 A JP21165788 A JP 21165788A JP 21165788 A JP21165788 A JP 21165788A JP H0262874 A JPH0262874 A JP H0262874A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- benzothiopyrylium
- compound expressed
- alkoxy
- 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
- 150000001875 compounds Chemical class 0.000 title abstract description 9
- NASMJMJQAAQVHI-UHFFFAOYSA-N thiochromenylium Chemical compound [S+]1=CC=CC2=CC=CC=C21 NASMJMJQAAQVHI-UHFFFAOYSA-N 0.000 title abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 150000001450 anions Chemical class 0.000 claims abstract description 3
- -1 benzothiopyrylium compound Chemical class 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 8
- 238000004040 coloring Methods 0.000 abstract description 4
- 239000004065 semiconductor Substances 0.000 abstract description 3
- 230000001476 alcoholic effect Effects 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000006606 n-butoxy group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- RUKJCCIJLIMGEP-ONEGZZNKSA-N 4-dimethylaminocinnamaldehyde Chemical compound CN(C)C1=CC=C(\C=C\C=O)C=C1 RUKJCCIJLIMGEP-ONEGZZNKSA-N 0.000 description 1
- YUUDIRJHGJPFBO-UHFFFAOYSA-N [O-]Cl(=O)(=O)=O.C=1C(C)[SH+]C2=CC=CC=C2C=1C1=CC=CC=C1 Chemical compound [O-]Cl(=O)(=O)=O.C=1C(C)[SH+]C2=CC=CC=C2C=1C1=CC=CC=C1 YUUDIRJHGJPFBO-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006608 n-octyloxy group Chemical group 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Landscapes
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は新規なベンゾチオピリリウム系化合物に関する
ものであり、詳しくは、染料、高分子の着色材料又は液
晶用二色性色素、電子写真プリンターの電子写真感光材
料、光デイスク用記録材料、近赤外線カットフィルター
用材料等の半導体レーザー利用分野等で有用なベンゾチ
オピリリウム系化合物及びその製造原料となるベンゾチ
オピリリウム系化合物に関するものである。Detailed Description of the Invention [Industrial Application Field] The present invention relates to a new benzothiopyrylium compound, and more specifically, it is used in dyes, polymeric coloring materials, dichroic dyes for liquid crystals, and electrophotography. This article relates to benzothiopyrylium compounds that are useful in semiconductor laser application fields such as electrophotographic materials for printers, recording materials for optical disks, and materials for near-infrared cut filters, and benzothiopyrylium compounds that are raw materials for their production. be.
［従来の技術及び発明が解決しようとする課題］従来よ
り、着色材料あるいは記録素材として有用な化合物につ
いては、種々提案がなされているが、未だ要求特性を十
分に満足し得るものは提供されておらず、各方面におい
て研究が続けられているのが現状である。[Prior Art and Problems to be Solved by the Invention] Various proposals have been made for compounds useful as coloring materials or recording materials, but no one has yet been provided that fully satisfies the required properties. Currently, research is continuing in various fields.
本発明は、新規な着色・記録素材として有用な新規ベン
ゾチオピリリウム系化合物を提供することを目的とする
。An object of the present invention is to provide a new benzothiopyrylium compound useful as a new coloring/recording material.
［課題を解決するための手段］ 本発明で提供されるベンゾチオピリリウム系化合物は、 一般式［１］ で表されるものである。[Means to solve the problem] The benzothiopyrylium compound provided by the present invention is General formula [1] It is expressed as
以下に本発明の詳細な説明する。The present invention will be explained in detail below.
上記一般式［Ｉ］において、ＲＩで示されるアルキル基
の具体例としては、メチル基、エチル基、ｎ−プロピル
基、ｎ−ブチル基、ｔｅｒｔ−ブチル基、ｎ−へブチル
基又はｎ−オクチル基等の直鎖状又は分岐状の炭素数１
〜８のアルキル基を挙げることができる。また、ＲＩで
示されるアルコキシ基の具体例としては、メトキシ基、
エトキシ基、ｎ−ブトキシ基、ｎ−へブチルオキシ基、
ｎ−オクチルオキシ基等の直鎮状又は分岐状の炭素数１
〜８のアルコキシ基を挙げることができる。In the above general formula [I], specific examples of the alkyl group represented by RI include methyl group, ethyl group, n-propyl group, n-butyl group, tert-butyl group, n-hebutyl group, or n-octyl group. Linear or branched group with 1 carbon number
-8 alkyl groups may be mentioned. Further, specific examples of the alkoxy group represented by RI include methoxy group,
Ethoxy group, n-butoxy group, n-hebutyloxy group,
Straight or branched carbon number 1 such as n-octyloxy group
-8 alkoxy groups may be mentioned.
Ｒ２で示されるアルコキシ基の具体例としては、メトキ
シ基、エトキシ基、ｎ−ブトキシ基、ｎ−へブチルオキ
シ基等の直鎖状又は分岐状の炭素数１〜９のアルコキシ
基を挙げることができる。Specific examples of the alkoxy group represented by R2 include linear or branched alkoxy groups having 1 to 9 carbon atoms such as methoxy group, ethoxy group, n-butoxy group, and n-hebutyloxy group. .
Ｒ３Ｒ４で示されるアルキル基の具体例としては、メチ
ル基、エチル基、ｎ−ブチル基、ｎ−ヘプチル基、ｎ−
オクチル基、ｎ−デシル基等の直鎖状又は分岐状の炭素
数１〜１０のアルキル基を挙げることができる。また、
Ｒ３、Ｒ４で示されるアルコキシ基で置換されたアルキ
ル基の具体例としては、メトキシエチル基、エトキシエ
チル基、ｎ−ブトキシエチル基、ｔａｒｔ−ブトキシエ
チル基等の直鎮状又は分岐状の炭素数２〜１０のアルコ
キシアルキル基を挙げることができる。Specific examples of the alkyl group represented by R3R4 include methyl group, ethyl group, n-butyl group, n-heptyl group, n-
Examples include linear or branched alkyl groups having 1 to 10 carbon atoms such as octyl group and n-decyl group. Also,
Specific examples of alkyl groups substituted with alkoxy groups represented by R3 and R4 include straight or branched carbon atoms such as methoxyethyl group, ethoxyethyl group, n-butoxyethyl group, and tart-butoxyethyl group. Mention may be made of 2 to 10 alkoxyalkyl groups.
Ｘｏで示される陰イオンとしては、ＣＪＺ Ｏ４”。The anion represented by Xo is CJZO4''.
の−価の有機又は無機の陰イオンを挙げることができる
。Mention may be made of organic or inorganic anions having a valence of .
本発明の一般式［１］で表されるベンゾチオピリリウム
系化合物は、例えば次の様にして製造することができる
。The benzothiopyrylium compound represented by the general formula [1] of the present invention can be produced, for example, as follows.
即ち、下記一般式［！■］
で表されるアルデヒド誘導体を、例えばエタノール等の
アルコール系溶媒中、２０〜１００℃で反応させること
により製造することができる。That is, the following general formula [! (2)] It can be produced by reacting the aldehyde derivative represented by, for example, in an alcoholic solvent such as ethanol at 20 to 100°C.
本発明の一般式［１］で表されるベンゾチオピリリウム
系化合物の具体例としては、以下のものが挙げられる。Specific examples of the benzothiopyrylium compound represented by the general formula [1] of the present invention include the following.
で表されるベンゾチオピリリウム系化合物と、下記一般
式［■コ
ＢＦ４゜
８Ｆ４’
記の実施例に限定されるものではない。A benzothiopyrylium compound represented by the following general formula [■BF4°8F4' is not limited to the examples described above.
実施例１
［実施例］
以下に実施例を挙げて本発明を更に具体的に説明するが
、本発明はその要旨を超えない限り、下２−メチル−４
−フェニル−１−ベンゾチオピリリウム過塩素酸塩ｏ、
ａｇ、ｐ−ジメチルアミノベンズアルデヒド０．５ｇ及
びエタノール１０ｍＩＬを混合し、室温で６時間反応さ
せた後放玲した。その後、エーテルを加え、析出する結
晶を濾過し、アセトンにて再結晶させて、上記化合物１
゜３ｇを得た。Example 1 [Example] The present invention will be described in more detail with reference to Examples below, but the present invention does not exceed the gist thereof.
-phenyl-1-benzothiopyrylium perchlorate o,
0.5 g of ag, p-dimethylaminobenzaldehyde and 10 mL of ethanol were mixed, reacted at room temperature for 6 hours, and then released. Then, ether was added, the precipitated crystals were filtered, and recrystallized with acetone to obtain the above compound 1.
3 g was obtained.
このものは、１５６℃で分解し、アセトン中の吸収スペ
クトル及び元素分析の結果は次の通りであることから、
上記構造式で示されるベンゾチオピリリウム系化合物で
あることが同定された。This substance decomposes at 156°C, and the absorption spectrum and elemental analysis results in acetone are as follows.
It was identified as a benzothiopyrylium compound represented by the above structural formula.
吸収スペクトル
んｍａｘ（ｇｘｌｏ’−’） ６９７（４，０９）元
Ｊｊし１ｍ
炭素
水素
窒素
Ｃ２ｓＨ２２Ｎ Ｓ
理論値
６２．９５
４．８６
２．９４
実施例２
Ｃ１１，０４・ Ｈ２Ｏ
測定値
６３．０５
４．５０
２．９３
２−メチル−４−フェニル−１−ベンゾチオピリリウム
過塩素酸塩０．６ｇ％ ｐ−ジメチルアミノシンナムア
ルデヒド０．４ｇ及びエタノール１０ｍＪ２を混合し、
室温で６時間反応させた後放冷した。その後、エーテル
を加え、析出する結晶を濾過し、アセトンにて再結晶さ
せて、上記化合物ｏ、６ｇを得た。Absorption spectrum max (gxlo'-') 697 (4,09) element Jj 1 m Carbon hydrogen nitrogen C2sH22N S Theoretical value 62.95 4.86 2.94 Example 2 C11,04・H2O Measured value 63.05 4 .50 2.93 2-Methyl-4-phenyl-1-benzothiopyrylium perchlorate 0.6g% p-Dimethylaminocinnamaldehyde 0.4g and ethanol 10mJ2 were mixed,
After reacting at room temperature for 6 hours, the mixture was allowed to cool. Thereafter, ether was added, and the precipitated crystals were filtered and recrystallized from acetone to obtain 6 g of the above compound o.
このものは、１６０℃で分解し、アセトン中の吸収スペ
クトル及び元素分析の結果は次の通りであることから、
上記構造式で示されるベンゾチオピリリウム系化合物で
あることが同定された。This substance decomposes at 160°C, and the absorption spectrum and elemental analysis results in acetone are as follows.
It was identified as a benzothiopyrylium compound represented by the above structural formula.
吸収スペクトル
λ１Ｉｌａｘ （ｅｘｌｏ−’） ７７Ｂ （１，
９７）及１」１を皿 Ｃ２７Ｈ２４ＮＳ−Ｃ１ｔｅ４・
７／２Ｈ２０理論値 測定値
炭素 ５８．２２ ５８．３７
水素 ５．６１ ５．３０
窒素 ２．５１ ２．５８
［発明の効果］
本発明で提供される新規なベンゾチオピリリウム系化合
物は、染料、着色材料、半導体レーザーを用いた各種の
表示、記録、記憶材料等に極めて有用である。Absorption spectrum λ1Ilax (exlo-') 77B (1,
97) and 1"1 plate C27H24NS-C1te4・
7/2H20 Theoretical value Measured value Carbon 58.22 58.37 Hydrogen 5.61 5.30 Nitrogen 2.51 2.58 [Effect of the invention] The novel benzothiopyrylium compound provided by the present invention can be used as a dye. , colored materials, and various display, recording, and memory materials using semiconductor lasers.
Claims (1)
基を示し、Ｒ＾２は水素原子又はアルコキシ基を示し、
Ｒ＾３、Ｒ＾４はアルコキシ基で置換されていてもよい
アルキル基を示し、 Ｘ＾■は陰イオンを示し、ｍ及びｎは１又は２を示す。 で表されるベンゾチオピリリウム系化合物。(1) General formula [I] ▲There are mathematical formulas, chemical formulas, tables, etc.▼... [I] [In the formula, R^1 represents a hydrogen atom, an alkyl group, or an alkoxy group, and R^2 represents a hydrogen atom or an alkoxy group. shows,
R^3 and R^4 represent an alkyl group which may be substituted with an alkoxy group, X^■ represents an anion, and m and n represent 1 or 2. A benzothiopyrylium compound represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21165788A JPH0262874A (en) | 1988-08-26 | 1988-08-26 | Benzothiopyrylium-based compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21165788A JPH0262874A (en) | 1988-08-26 | 1988-08-26 | Benzothiopyrylium-based compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0262874A true JPH0262874A (en) | 1990-03-02 |
Family
ID=16609427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21165788A Pending JPH0262874A (en) | 1988-08-26 | 1988-08-26 | Benzothiopyrylium-based compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0262874A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5200665A (en) * | 1990-11-21 | 1993-04-06 | Nisca Corporation | Ultrasonic actuator |
| US5300851A (en) * | 1991-10-31 | 1994-04-05 | Matsushita Electric Industrial Co., Ltd. | Linear-type actuator |
-
1988
- 1988-08-26 JP JP21165788A patent/JPH0262874A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5200665A (en) * | 1990-11-21 | 1993-04-06 | Nisca Corporation | Ultrasonic actuator |
| US5300851A (en) * | 1991-10-31 | 1994-04-05 | Matsushita Electric Industrial Co., Ltd. | Linear-type actuator |
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