JPH0360819B2 - - Google Patents
Info
- Publication number
- JPH0360819B2 JPH0360819B2 JP22147186A JP22147186A JPH0360819B2 JP H0360819 B2 JPH0360819 B2 JP H0360819B2 JP 22147186 A JP22147186 A JP 22147186A JP 22147186 A JP22147186 A JP 22147186A JP H0360819 B2 JPH0360819 B2 JP H0360819B2
- Authority
- JP
- Japan
- Prior art keywords
- light
- compound
- general formula
- formula
- mmol
- 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
Links
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical class N* 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000009102 absorption Effects 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 238000000862 absorption spectrum Methods 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- -1 lithium aluminum hydride Chemical compound 0.000 description 7
- 230000003287 optical effect Effects 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000015654 memory Effects 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 4
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical class C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 235000000177 Indigofera tinctoria Nutrition 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 238000000434 field desorption mass spectrometry Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940097275 indigo Drugs 0.000 description 2
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 150000002829 nitrogen Chemical class 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- UIZLQMLDSWKZGC-UHFFFAOYSA-N cadmium helium Chemical compound [He].[Cd] UIZLQMLDSWKZGC-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- CPBQJMYROZQQJC-UHFFFAOYSA-N helium neon Chemical compound [He].[Ne] CPBQJMYROZQQJC-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GRYKQRDKTNFJQN-UHFFFAOYSA-N methyl 4-acetyl-5-methylthiophene-2-carboxylate Chemical compound COC(=O)C1=CC(C(C)=O)=C(C)S1 GRYKQRDKTNFJQN-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006349 photocyclization reaction Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
Landscapes
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22147186A JPS6377876A (ja) | 1986-09-19 | 1986-09-19 | フオトクロミツク化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22147186A JPS6377876A (ja) | 1986-09-19 | 1986-09-19 | フオトクロミツク化合物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6377876A JPS6377876A (ja) | 1988-04-08 |
| JPH0360819B2 true JPH0360819B2 (fr) | 1991-09-17 |
Family
ID=16767234
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22147186A Granted JPS6377876A (ja) | 1986-09-19 | 1986-09-19 | フオトクロミツク化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6377876A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008280289A (ja) * | 2007-05-10 | 2008-11-20 | Jfe Chemical Corp | １−メチレンインダン骨格を有する不飽和化合物の製造方法 |
-
1986
- 1986-09-19 JP JP22147186A patent/JPS6377876A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6377876A (ja) | 1988-04-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4287337A (en) | Spiropyran compounds of piperidine or thiazine rings | |
| Irie et al. | Photochromic diarylethenes with intralocking arms | |
| JP4025920B2 (ja) | フォトクロミック材料 | |
| JPH075572B2 (ja) | ２―［２―（２―ヒドロキシフェニル）ビニルピラジンおよびその製造法 | |
| Shibata et al. | Extraordinarily low cycloreversion quantum yields of photochromic diarylethenes with methoxy substituents | |
| JPH08245579A (ja) | ジアリールエテン系フォトクロミック化合物および該化合物を用いた光学記録材料 | |
| Frigoli et al. | Photomodulable materials. Synthesis and properties of photochromic 3H‐naphtho [2, 1‐b] pyrans linked to thiophene units via an acetylenic junction | |
| JPH04297480A (ja) | インドリノスピロベンゾチオピラン誘導体とその開環型異性体を含むことからなる結晶、その製造方法及び該結晶からなるピエゾクロミック材料 | |
| Mahmoodi et al. | Photochromism of several synthesised 1, 3-diazabicyclo [3, 1, 0] hex-3-ene derivatives | |
| Leonard et al. | Chalcogenopyranones from disodium chalcogenide additions to 1, 4‐pentadiyn‐3‐ones. The role of enol ethers as intermediates | |
| JPH0360819B2 (fr) | ||
| JPH02226141A (ja) | フォトクロミック材料 | |
| Watkins et al. | Synthesis, characterization, and solvent-independent photochromism of spironaphthooxazine dimers | |
| Kose | Novel sulfoxide-introducing reaction and photochromic reactions of ethenylsulfinyl derivatives of dithienylethenes | |
| JPH0798934B2 (ja) | フォトクロミック材料および光学記録媒体 | |
| FR2821357A1 (fr) | Nouveaux thiacalix[4]arenes et leurs complexes metalliques | |
| JP2881538B2 (ja) | インドリジン系色素および溶解性向上方法 | |
| Luyksaar et al. | Synthesis of photochromic bisfulgimides by the condensation of (3 Z)-3-[1-(2, 5-dimethyl-3-thienyl)-ethylidene]-4-isopropylidene-2, 5-furandione with aromatic diamines | |
| JPH0559025A (ja) | ジアリールエテン系化合物 | |
| JP3819629B2 (ja) | 光学活性フォトクロミック結晶材料 | |
| JP2591042B2 (ja) | ナフタセン誘導体 | |
| JP3479992B2 (ja) | 鍵付フォトクロミック分子 | |
| JPH0413354B2 (fr) | ||
| JPH04283595A (ja) | 遷移金属スピロベンゾピラン錯体、その製造方法及び該錯体からなるフォトクロミック材料 | |
| JPH0549717B2 (fr) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |