JPH04243874A - Tellurophene-based compound - Google Patents
Tellurophene-based compoundInfo
- Publication number
- JPH04243874A JPH04243874A JP3006378A JP637891A JPH04243874A JP H04243874 A JPH04243874 A JP H04243874A JP 3006378 A JP3006378 A JP 3006378A JP 637891 A JP637891 A JP 637891A JP H04243874 A JPH04243874 A JP H04243874A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- expressed
- formula
- tellurophene
- afford
- 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 11
- TULWUZJYDBGXMY-UHFFFAOYSA-N tellurophene Chemical compound [Te]1C=CC=C1 TULWUZJYDBGXMY-UHFFFAOYSA-N 0.000 title abstract 2
- 239000000126 substance Substances 0.000 claims abstract description 16
- 125000002252 acyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- -1 tellurophene compound Chemical class 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000005087 tellurophenes Chemical class 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract description 4
- 238000010992 reflux Methods 0.000 abstract description 4
- NLLILAUVOOREKR-UHFFFAOYSA-N 3-methylhexane-2,5-dione Chemical compound CC(=O)C(C)CC(C)=O NLLILAUVOOREKR-UHFFFAOYSA-N 0.000 abstract description 3
- OIMRLHCSLQUXLL-UHFFFAOYSA-N 3-chlorobutan-2-one Chemical compound CC(Cl)C(C)=O OIMRLHCSLQUXLL-UHFFFAOYSA-N 0.000 abstract description 2
- CQYLSOVNYJDNEY-UHFFFAOYSA-N ethyl 2-acetyl-3-methyl-4-oxopentanoate Chemical compound CCOC(=O)C(C(C)=O)C(C)C(C)=O CQYLSOVNYJDNEY-UHFFFAOYSA-N 0.000 abstract description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 230000000802 nitrating effect Effects 0.000 abstract description 2
- 239000011574 phosphorus Substances 0.000 abstract description 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XHTPGMULOYWSIK-UHFFFAOYSA-N 2,3,5-trimethylselenophene Chemical compound CC1=CC(C)=C(C)[se]1 XHTPGMULOYWSIK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000007699 photoisomerization reaction Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- XSOKHXFFCGXDJZ-UHFFFAOYSA-N telluride(2-) Chemical compound [Te-2] XSOKHXFFCGXDJZ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Optical Record Carriers And Manufacture Thereof (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】本発明は、新規なテルロフェン系
化合物に関する。詳細には、光照射に伴い可逆的にな構
造的変化が生じる、いわゆる、フォトクロミック特性を
持つテルロフェン化合物、および、それを利用したメモ
リ材料に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to novel tellurophene compounds. In particular, the present invention relates to a tellurophene compound having so-called photochromic properties, which undergoes a reversible structural change upon irradiation with light, and to a memory material using the same.
【０００２】0002
【従来の技術】従来のメモリ媒体としては、磁気メモリ
、光磁気メモリが存在するが、それらと比べた場合、フ
ォトクロミック材料は、メモリ密度で、磁気メモリの数
十倍、光磁気メモリの数倍、データー転送速度は、それ
ぞれの、１０〜３０倍と３０〜５０倍程度のメモリ材料
となり得る。しかし、従来、研究されてきたフォトクロ
ミック材料は、その異性体のいずれかは熱的に不安定で
あり、安定な異性体へと変換しやすく、メモリ材料とし
ての使用を考えた場合、長期間における保存性および再
生時の安定性（読み出し光に対する安定性）について信
頼性が乏しかった。[Prior Art] Conventional memory media include magnetic memory and magneto-optical memory, but compared to these, photochromic materials have a memory density that is several tens of times that of magnetic memory and several times that of magneto-optical memory. , the data transfer rate can be on the order of 10 to 30 times and 30 to 50 times that of the memory materials, respectively. However, in the photochromic materials that have been studied in the past, one of their isomers is thermally unstable and easily converts to a stable isomer, so when considering use as a memory material, it is difficult to maintain long-term stability. The storage stability and stability during playback (stability against readout light) were unreliable.
【０００３】0003
【発明が解決しようとする課題】本発明の目的はフォト
クロミック特性を持ち、しかもいずれの異性体において
も安定な、新規なテルロフェン化合物を提供することで
ある。SUMMARY OF THE INVENTION An object of the present invention is to provide a novel tellurophene compound which has photochromic properties and is stable in any isomer form.
【０００４】0004
【課題を解決するための手段】本発明のテルロフェン化
合物は化学式（Ｉ）[Means for Solving the Problems] The tellurophene compound of the present invention has the chemical formula (I)
【０００５】[0005]
【化２】[Case 2]
【０００６】（式中、置換基Ｒ１、Ｒ２、Ｒ３、Ｒ４、
Ｒ５およびＲ６は、同一または異なっていてもよく、少
なくとも一つは炭素を含む基、−Ｈ、または−Ｘを表す
（Ｘ＝Ｆ、Ｃｌ、Ｂｒ、Ｉ））で表される物質であり、
望ましくは、Ｒ１〜Ｒ６が、同一であることを特徴とす
る。また、更に望ましい本発明のテルロフェン化合物は
、置換基が−ＣＨ３あるいは、−Ｂｒであることを特徴
とし、好適にはＲ１およびＲ４が、ともに−Ｈ、アシル
基あるいは−Ｘであることを特徴とする。(wherein the substituents R1, R2, R3, R4,
R5 and R6 may be the same or different, and at least one is a substance represented by a carbon-containing group, -H, or -X (X = F, Cl, Br, I),
Preferably, R1 to R6 are the same. Further, a more desirable tellurophene compound of the present invention is characterized in that the substituent is -CH3 or -Br, preferably both R1 and R4 are -H, an acyl group or -X. do.
【０００７】[0007]
【作用】本発明の構成によれば、化学式（ＩＩ）にある
ように構造Ａの物質に、特定波長（λ１）の光を照射す
ることにより、構造の変化をおこし構造Ｂとなる。また
構造Ｂの物質に、別の特定波長（λ２）を当てると、元
の構造Ａにもどる。この間この両物質間には、分子量変
化はないが、構造変化が生じ吸収波長が変化する。[Operation] According to the structure of the present invention, by irradiating a substance of structure A with light of a specific wavelength (λ1) as shown in chemical formula (II), the structure changes to become structure B. Furthermore, when another specific wavelength (λ2) is applied to the substance of structure B, it returns to the original structure A. During this time, there is no change in molecular weight between the two substances, but a structural change occurs and the absorption wavelength changes.
【０００８】[0008]
【化３】[Chemical formula 3]
【０００９】（化学式（ＩＩ）のいずれの異性体および
それらの混合物も本発明に包含される。）これらの物質
はそれぞれの状態で構造的に安定であり熱的にも安定で
ある。(Any isomers of formula (II) and mixtures thereof are included in the present invention.) These substances are structurally stable and thermally stable in their respective states.
【００１０】0010
【実施例】本発明による化学式（Ｉ）で表される化合物
は、複素五員環を生成し、ニトロ化した後、それを還元
することで製造することができる。EXAMPLES The compound represented by the chemical formula (I) according to the present invention can be produced by forming a five-membered heterocyclic ring, nitrating it, and then reducing it.
【００１１】化学式（Ｉ）の化合物の一つである３，３
´−アゾビス（２，４，５−トリメチルセレノフェン）
、は化学式（ＩＩＩ）で示すようにして得ることができ
る。以下にその製造法を示す。3,3, which is one of the compounds of formula (I)
´-Azobis(2,4,5-trimethylselenophene)
can be obtained as shown in chemical formula (III). The manufacturing method is shown below.
【００１２】0012
【化４】[C4]
【００１３】（化学式（ＩＩＩ）において、Ｒ１、Ｒ２
、Ｒ３、Ｒ４、Ｒ５およびＲ６は、化学式（Ｉ）で定義
した通りである。）
［製造例］３，３´−アゾビス（２，４，５−トリメチ
ルテルロフェン）の製造法
（反応１）２，３ージアセチルブタン酸エチルの生成エ
タノール（４０ｍｌ）にナトリウム（０．２４ｇ）入れ
かくはんした。ナトリウム溶解後ナトリウムエチラート
（１３．１ｇ）を入れ、０℃に冷却しながらかくはんし
た。アセト酢酸エチル（４１．８ｇ）をゆっくり滴下し
、続いて３ークロロー２ーブタノン（１７．１ｇ）を滴
下した。室温で２時間かくはんした後、１時間還流した
。塩酸で中和後、エーテルで抽出、硫酸マグネシウムで
乾燥、分留し、２，３ージアセチルブタン酸エチルを１
３．５６ｇ得た（収率５０．２）。(In chemical formula (III), R1, R2
, R3, R4, R5 and R6 are as defined in formula (I). ) [Production Example] Production method of 3,3'-azobis(2,4,5-trimethyltellophene) (Reaction 1) Production of ethyl 2,3-diacetylbutanoate Sodium (0.24 g) in ethanol (40 ml) I stirred it up. After dissolving the sodium, sodium ethylate (13.1 g) was added and stirred while cooling to 0°C. Ethyl acetoacetate (41.8 g) was slowly added dropwise, followed by 3-chloro-2-butanone (17.1 g). After stirring at room temperature for 2 hours, the mixture was refluxed for 1 hour. After neutralization with hydrochloric acid, extraction with ether, drying over magnesium sulfate, and fractional distillation, ethyl 2,3-diacetylbutanoate was extracted with 1
3.56g was obtained (yield 50.2).
【００１４】
（反応２）３ーメチルー２，５ーヘキサジオンの生成２
，３ージアセチルブタン酸エチル（１３．３ｇ）に水８
００ｃｃ、炭酸カリウム（２７．７ｇ）を加え、数時間
加熱還流した。次に、エーテルで抽出を行い、脱水し、
エーテルを除いて、３ーメチルー２，５ーヘキサンジオ
ンを７．２６２ｇ得た（収率６６．４）。(Reaction 2) Production of 3-methyl-2,5-hexadione 2
, ethyl 3-diacetylbutanoate (13.3g) and water 8
00 cc and potassium carbonate (27.7 g) were added, and the mixture was heated under reflux for several hours. Next, extract with ether, dehydrate,
After removing the ether, 7.262 g of 3-methyl-2,5-hexanedione was obtained (yield: 66.4).
【００１５】
（反応３）２，３，５−トリメチルテルロフェンの生成
５テルル化リン（９．８ｇ）に３ーメチルー２，５ーヘ
キサンジオン（７．１ｇ）を滴下し、１８０℃で１時間
加熱した。加熱後、室温で反応液に水酸ナトリウム水溶
液を加えた。ガスの発生が収まった後、エーテルで抽出
し、乾燥後、エーテルを留去して、２，３，５−トリメ
チルテルロフェンを２．５３５ｇ得た（収率２０．５％
）。(Reaction 3) Production of 2,3,5-trimethyltellurophene 3-methyl-2,5-hexanedione (7.1 g) was added dropwise to 5-phosphorus telluride (9.8 g) and heated at 180° C. for 1 hour. . After heating, an aqueous sodium hydroxide solution was added to the reaction mixture at room temperature. After the gas generation subsided, extraction was performed with ether, and after drying, the ether was distilled off to obtain 2.535 g of 2,3,5-trimethyltellurophene (yield: 20.5%).
).
【００１６】
（反応４）２，３，５−トリメチル−４−ニトロテルロ
フェンの生成
無水酢酸（１２．４ｍｌ）を氷浴中で冷却し、６０％の
硝酸（２．１ｍｌ）をゆっくりと加え、さらに硫酸（一
滴）を加えた。その溶液をよくかき混ぜながら、２，３
，５−トリメチルテルロフェン（２．４ｇ）を少量ずつ
滴下した。この間反応温度は０〜５℃に保つ。反応混合
物を０〜５℃で３０分間かき混ぜ、水酸化ナトリウム（
１１．０ｇ）を水１５０ｍｌに溶かした溶液を０℃に冷
却して中和する。その後、クロロホルムで抽出した。
乾燥後、溶媒を留去し、２，３，５−トリメチル−４−
ニトロテルロフェンを１．３５６ｇ得た（収率４６．２
％）。(Reaction 4) Production of 2,3,5-trimethyl-4-nitrotellrophene Acetic anhydride (12.4 ml) was cooled in an ice bath, and 60% nitric acid (2.1 ml) was slowly added. , and added sulfuric acid (one drop). While stirring the solution well,
, 5-trimethyltellurophene (2.4 g) was added dropwise little by little. During this time, the reaction temperature is maintained at 0 to 5°C. The reaction mixture was stirred for 30 min at 0-5 °C and then treated with sodium hydroxide (
A solution of 11.0 g) dissolved in 150 ml of water is cooled to 0°C and neutralized. Then, it was extracted with chloroform. After drying, the solvent was distilled off and 2,3,5-trimethyl-4-
1.356g of nitrotellrofene was obtained (yield: 46.2
%).
【００１７】
（反応５）３，３´−アゾビス（２，４，５−
トリメチルテルロフェン）の生成
エタノール（７．６ｍｌ）、１２Ｍ水酸化ナトリウム溶
液（１．３ｍｌ）に、２，３，５−トリメチル−４−ニ
トロテルロフェン（１．１ｇ）を入れ、加熱還流しなが
ら、亜鉛末（２．１ｇ）をゆっくり少量ずつ加えていっ
た。加え終わったらそのまま３０分間還流を続けた。次
に反応混合物を濾別し、精製して、標題化合物を０．１
４６ｇ得た（収率１５．６％）。(Reaction 5) 3,3'-azobis(2,4,5-
2,3,5-trimethyl-4-nitrotellurophen (1.1 g) was added to ethanol (7.6 ml) and 12M sodium hydroxide solution (1.3 ml), and the mixture was heated under reflux. Then, zinc dust (2.1 g) was slowly added little by little. After the addition was completed, reflux was continued for 30 minutes. The reaction mixture was then filtered and purified to give the title compound at 0.1
46g was obtained (yield 15.6%).
【００１８】
次に、標題化合物の光異性化反応式を化学式（ＩＶ
）に示し、図１に、その各構造における吸収スペクトル
を示す。Next, the photoisomerization reaction formula of the title compound is expressed as the chemical formula (IV
), and FIG. 1 shows the absorption spectra of each structure.
【００１９】[0019]
【化５】[C5]
【００２０】さらに、Ｃ，Ｄいずれの構造の物質も８０
℃の温度においてほとんど劣化を示さなかった。Furthermore, substances with both C and D structures have 80
It showed almost no deterioration at temperatures of .
【００２１】[0021]
【発明の効果】以上述べたように、本発明によるフォト
クロミック特性を持つテルロフェン化合物は、メモリ材
料として有効であるという効果を有する。As described above, the tellurophene compound having photochromic properties according to the present invention has the effect of being effective as a memory material.
【図１】異性化反応を示した化学式（ＩＶ）の構造Ｃ、
Ｄにおける吸収スペクトル図である。[Figure 1] Structure C of chemical formula (IV) showing an isomerization reaction,
It is an absorption spectrum diagram in D.
Claims (6)
系化合物。 【化１】 （式中、置換基Ｒ１、Ｒ２、Ｒ３、Ｒ４、Ｒ５およびＲ
６は、同一または異なっていてもよく、少なくとも一つ
は炭素を含む基、−Ｈ、または−Ｘを表す（Ｘ＝Ｆ、Ｃ
ｌ、Ｂｒ、Ｉ））[Claim 1] A tellurophene compound represented by the chemical formula (I). embedded image (wherein the substituents R1, R2, R3, R4, R5 and R
6 may be the same or different, and at least one represents a carbon-containing group, -H, or -X (X=F, C
l, Br, I))
シル基である、請求項１記載のテルロフェン系化合物。2. The tellurophene compound according to claim 1, wherein the substituent is an alkyl group or an acyl group.
記載のテルロフェン系化合物。3. Claim 1, wherein the substituents are the same.
The tellurophene compounds described.
載のテルロフェン系化合物。4. The tellurophene compound according to claim 3, wherein the substituent is -CH3.
テルロフェン系化合物。5. The tellurophene compound according to claim 3, wherein the substituent is -Br.
ル基あるいは−Ｘである、請求項１記載のテルロフェン
系化合物。6. The tellurophene compound according to claim 1, wherein R1 and R4 are both -H, an acyl group, or -X.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3006378A JPH04243874A (en) | 1991-01-23 | 1991-01-23 | Tellurophene-based compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3006378A JPH04243874A (en) | 1991-01-23 | 1991-01-23 | Tellurophene-based compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04243874A true JPH04243874A (en) | 1992-08-31 |
Family
ID=11636721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3006378A Pending JPH04243874A (en) | 1991-01-23 | 1991-01-23 | Tellurophene-based compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04243874A (en) |
-
1991
- 1991-01-23 JP JP3006378A patent/JPH04243874A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3341090B2 (en) | Oxadiazole derivative and method for producing the same | |
| JP2002105055A (en) | Method for manufacturing indium complex or its tautomer | |
| JP2009073750A (en) | Method for producing bipyridinium compound and its synthetic intermediate, method for producing coloring compound, and new bipyridinium compound and new coloring compound containing the same | |
| JPH08245579A (en) | Diarylethene photochromic compound and optically recording material using the compound | |
| Heynderickx et al. | Sulfinyl-and sulfonyl-substituted 2-benzylbenzoxazoles and 2-benzylbenzothiazoles as potential photochromic compounds | |
| JPH04243874A (en) | Tellurophene-based compound | |
| JPH04243873A (en) | Selenophene-based compound | |
| JP2009149589A (en) | Process for producing asymmetric monoazamethine cyanine | |
| JPH04243862A (en) | Pyrrole-based compound | |
| JP2581118B2 (en) | Optical recording medium | |
| RU2005107785A (en) | METHOD FOR PRODUCING NO-DONOR COMPOUNDS SUCH AS NO-DONOR DICLOFENAC | |
| JP2007112748A (en) | Chlorine-substituted porphyrin compound and method for producing chlorine-substituted porphyrin compound | |
| JP4244560B2 (en) | Novel compounds useful for optical switching, etc. and methods for producing the same | |
| JP2006188582A (en) | New pyrazolone compound and merocyanine coloring matter using it | |
| Kokars et al. | Synthesis of 2-azastilbene derivatives with intramolecular charge transfer | |
| JPH051233A (en) | Indole compound | |
| JP4599801B2 (en) | Thia / oxaporphyrin compounds | |
| JPH051231A (en) | Furan compound | |
| JP3109903B2 (en) | Asymmetric 9-aminostyryl-10-styrylanthracene derivatives and process for producing the same | |
| JPH11322698A (en) | Azamethine and its production | |
| JP4105821B2 (en) | Diazo compounds | |
| Inoue et al. | Sydnones. Synthesis and Photochromic Behavior of 3-(3-Pyridyl) sydnone Derivatives and a 4-Alkenyl-3-phenylsydnone | |
| JPH0549717B2 (en) | ||
| JPH051056A (en) | Benzothiophene compound | |
| JP3182840B2 (en) | Method for producing photochromic maleimide derivative |