JPS6348265A - 非線形光学用有機材料 - Google Patents
非線形光学用有機材料Info
- Publication number
- JPS6348265A JPS6348265A JP19240486A JP19240486A JPS6348265A JP S6348265 A JPS6348265 A JP S6348265A JP 19240486 A JP19240486 A JP 19240486A JP 19240486 A JP19240486 A JP 19240486A JP S6348265 A JPS6348265 A JP S6348265A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyridinium
- vinyl
- hydroxyphenyl
- dimethylamino
- 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.)
- Granted
Links
- 239000011368 organic material Substances 0.000 title claims abstract description 7
- 230000003287 optical effect Effects 0.000 title abstract description 21
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 15
- DSVVHRZFPREHDR-UHFFFAOYSA-O 4-(2-pyridin-1-ium-1-ylethenyl)phenol Chemical compound C1=CC(O)=CC=C1C=C[N+]1=CC=CC=C1 DSVVHRZFPREHDR-UHFFFAOYSA-O 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims 2
- YMJLEUUSHBPBFN-UHFFFAOYSA-N n,n-dimethyl-4-(2-pyridin-1-ium-1-ylethenyl)aniline Chemical compound C1=CC(N(C)C)=CC=C1C=C[N+]1=CC=CC=C1 YMJLEUUSHBPBFN-UHFFFAOYSA-N 0.000 claims 1
- 239000013078 crystal Substances 0.000 abstract description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 abstract description 18
- 239000000463 material Substances 0.000 abstract description 13
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 11
- 229920002554 vinyl polymer Polymers 0.000 abstract description 11
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 abstract description 6
- -1 p-toluenesulfonyl Chemical group 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 3
- 238000001704 evaporation Methods 0.000 abstract description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract description 3
- WDRZVZVXHZNSFG-UHFFFAOYSA-N 1-ethenylpyridin-1-ium Chemical compound C=C[N+]1=CC=CC=C1 WDRZVZVXHZNSFG-UHFFFAOYSA-N 0.000 abstract description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 abstract description 2
- 230000018044 dehydration Effects 0.000 abstract description 2
- 238000006297 dehydration reaction Methods 0.000 abstract description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 abstract 2
- QNKQRUCMNFOSEK-UHFFFAOYSA-N 4-methylbenzenesulfonate;4-[2-(1-methylpyridin-1-ium-4-yl)ethenyl]phenol Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=C[N+](C)=CC=C1C=CC1=CC=C(O)C=C1 QNKQRUCMNFOSEK-UHFFFAOYSA-N 0.000 abstract 1
- TWUHCNLNXXJOHV-UHFFFAOYSA-N C[N+]1(CC=C(C=C1)C)[N+]1=CC=CC=C1 Chemical compound C[N+]1(CC=C(C=C1)C)[N+]1=CC=CC=C1 TWUHCNLNXXJOHV-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000000694 effects Effects 0.000 description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 239000004202 carbamide Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WVKVDDALQQZUGC-UHFFFAOYSA-N 4-[4-(dimethylamino)styryl]-N-methylpyridinium Chemical compound C1=CC(N(C)C)=CC=C1C=CC1=CC=[N+](C)C=C1 WVKVDDALQQZUGC-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 229910021612 Silver iodide Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229940045105 silver iodide Drugs 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- DBOHWMPKJCJANT-UHFFFAOYSA-O 4-[2-(1-methyl-1h-pyridin-1-ium-4-ylidene)ethylidene]cyclohexa-2,5-dien-1-one Chemical compound C1=C[N+](C)=CC=C1C=CC1=CC=C(O)C=C1 DBOHWMPKJCJANT-UHFFFAOYSA-O 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YOBTXORLVXZWSR-UHFFFAOYSA-M 1,4-dimethylpyridin-1-ium;iodide Chemical compound [I-].CC1=CC=[N+](C)C=C1 YOBTXORLVXZWSR-UHFFFAOYSA-M 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000019796 monopotassium phosphate Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- NZSWYXAQUBELKN-UHFFFAOYSA-N 4-(2-pyridin-4-ylethenyl)phenol Chemical compound C1=CC(O)=CC=C1C=CC1=CC=NC=C1 NZSWYXAQUBELKN-UHFFFAOYSA-N 0.000 description 1
- PUVMUAOIOKUCRI-UHFFFAOYSA-N 4-[2-(1-methylpyridin-1-ium-4-yl)ethenyl]phenol;iodide Chemical compound [I-].C1=C[N+](C)=CC=C1\C=C\C1=CC=C(O)C=C1 PUVMUAOIOKUCRI-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 229910003327 LiNbO3 Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- XQNXLVUPJKQLPU-UHFFFAOYSA-M n,n-dimethyl-4-[2-(1-methylpyridin-1-ium-4-yl)ethenyl]aniline;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC(N(C)C)=CC=C1C=CC1=CC=[N+](C)C=C1 XQNXLVUPJKQLPU-UHFFFAOYSA-M 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 230000008832 photodamage Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- JUDUFOKGIZUSFP-UHFFFAOYSA-M silver;4-methylbenzenesulfonate Chemical compound [Ag+].CC1=CC=C(S([O-])(=O)=O)C=C1 JUDUFOKGIZUSFP-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19240486A JPS6348265A (ja) | 1986-08-18 | 1986-08-18 | 非線形光学用有機材料 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19240486A JPS6348265A (ja) | 1986-08-18 | 1986-08-18 | 非線形光学用有機材料 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11213390A Division JPH02297529A (ja) | 1990-04-27 | 1990-04-27 | 非線形光学用有機材料 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6348265A true JPS6348265A (ja) | 1988-02-29 |
| JPH034547B2 JPH034547B2 (enrdf_load_stackoverflow) | 1991-01-23 |
Family
ID=16290753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19240486A Granted JPS6348265A (ja) | 1986-08-18 | 1986-08-18 | 非線形光学用有機材料 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6348265A (enrdf_load_stackoverflow) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62211622A (ja) * | 1986-03-12 | 1987-09-17 | Nippon Telegr & Teleph Corp <Ntt> | 非線形光学装置 |
-
1986
- 1986-08-18 JP JP19240486A patent/JPS6348265A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62211622A (ja) * | 1986-03-12 | 1987-09-17 | Nippon Telegr & Teleph Corp <Ntt> | 非線形光学装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH034547B2 (enrdf_load_stackoverflow) | 1991-01-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |