PL213577B1 - New non-linear-optical manometer and its production method - Google Patents
New non-linear-optical manometer and its production methodInfo
- Publication number
- PL213577B1 PL213577B1 PL380843A PL38084306A PL213577B1 PL 213577 B1 PL213577 B1 PL 213577B1 PL 380843 A PL380843 A PL 380843A PL 38084306 A PL38084306 A PL 38084306A PL 213577 B1 PL213577 B1 PL 213577B1
- Authority
- PL
- Poland
- Prior art keywords
- methylisoxazole
- optical
- hydroxyethyl
- linear
- mixture
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000178 monomer Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 7
- FKPXGNGUVSHWQQ-UHFFFAOYSA-N 5-methyl-1,2-oxazol-3-amine Chemical compound CC1=CC(N)=NO1 FKPXGNGUVSHWQQ-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- -1 (2-hydroxyethyl) phenylazo Chemical group 0.000 claims description 4
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 claims description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 239000012954 diazonium Substances 0.000 claims description 3
- 150000001989 diazonium salts Chemical class 0.000 claims description 3
- 238000006193 diazotization reaction Methods 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 239000004317 sodium nitrate Substances 0.000 claims description 2
- 235000010344 sodium nitrate Nutrition 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- CUMCMYMKECWGHO-UHFFFAOYSA-N 3-methyl-1,2-oxazole Chemical group CC=1C=CON=1 CUMCMYMKECWGHO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 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
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 239000000382 optic material Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest nowy nieliniowo-optyczny monomer, będący pochodną 3-amino-5-metyloizoksazolu.The subject of the invention is a new nonlinear-optical monomer which is a derivative of 3-amino-5-methylisoxazole.
Przedmiotem wynalazku jest też sposób wytwarzania nowego nieliniowo-optycznego monomeru.The invention also relates to a method for producing a new nonlinear-optical monomer.
Z publikacji A.D. Towns, Dyes and Pigments, 42 (1999) 3-28 oraz M. Wang, K. Funabiki, M. Matsui, Dyes and Pigments, 57 (2003) 77-86 i Z. Yuxia. L. Zhao, Q. Ling, Z. Jianfen, Z. Jiayun, S. Yuquan, X. Gang, Y. Peixian, European Polymer Journal, 37 (2001) 445-449, znane są chromofory i monomery o właściwościach nieliniowo-optycznych, zawierające w swojej cząsteczce pierścień heterocykliczny, połączony z ugrupowaniem benzenowym za pośrednictwem wiązania azowego.From the publication of A.D. Towns, Dyes and Pigments, 42 (1999) 3-28 and M. Wang, K. Funabiki, M. Matsui, Dyes and Pigments, 57 (2003) 77-86 and Z. Yuxia. L. Zhao, Q. Ling, Z. Jianfen, Z. Jiayun, S. Yuquan, X. Gang, Y. Peixian, European Polymer Journal, 37 (2001) 445-449, chromophores and monomers with nonlinear-optical properties are known containing a heterocyclic ring in its molecule, connected to the benzene moiety via an azo bond.
Wynalazek dotyczy nowego nieliniowo-optycznego monomeru o nazwie 3-(4'-N,N-di(2-hydroksyetylo)fenyloazo)-5-metyloizoksazol i wzorze przedstawionym na rysunku, który jest pochodną 3-amino-5-metyloizoksazolu. Nowy związek zawiera ugrupowanie heterocykliczne nie stosowane dotychczas w syntezie nieliniowych monomerów. Nowy związek jest rozpuszczalny w ogólnie dostępnych rozpuszczalnikach organicznych takich jak: aceton, tetrahydrofuran (THF), N,N-dimetyloformamid (DMF), pirydyna. Związek ten może być poddawany dalszym reakcjom prowadzącym do otrzymania fotochromowych i nieliniowo-optycznych materiałów, znajdujących zastosowanie w optoelektronice i optyce nieliniowej, np. do generacji drugiej harmonicznej.The invention relates to a novel non-linear optical monomer named 3- (4'-N, N-di (2-hydroxyethyl) phenylazo) -5-methylisoxazole and the formula shown in the figure which is a derivative of 3-amino-5-methylisoxazole. The new compound contains a heterocyclic moiety that has not been used so far in the synthesis of non-linear monomers. The new compound is soluble in generally available organic solvents such as: acetone, tetrahydrofuran (THF), N, N-dimethylformamide (DMF), pyridine. This compound can be subjected to further reactions leading to the obtaining of photochromic and nonlinear-optic materials that can be used in optoelectronics and nonlinear optics, e.g. for the generation of the second harmonic.
Sposób wytwarzania nowego 3-(4'-N,N-di(2-hydroksyetylo)fenyloazo)-5-metyloizoksazolu obejmuje reakcję diazowania 3-amino-5-metyloizoksazolu, a następnie sprzęgania otrzymanej soli diazoniowej z N,N-di(2-hydroksyetylo)aniliną.The method of producing the new 3- (4'-N, N-di (2-hydroxyethyl) phenylazo) -5-methylisoxazole involves the diazotization of 3-amino-5-methylisoxazole, followed by coupling the obtained diazonium salt with N, N-di (2 -hydroxyethyl) aniline.
Sposób według wynalazku polega na tym, że 3-amino-5-metyloizoksazol poddaje się reakcji diazowania za pomocą mieszaniny stężonego kwasu siarkowego i wodnego roztworu azotan sodu (III), a następnie otrzymaną sól diazoniową sprzęga się z N,N-di(2-hydroksyetylo)aniliną. Otrzymany produkt reakcji po wytrąceniu z mieszaniny reakcyjnej i wysuszeniu, oczyszcza się przez krystalizację z mieszaniny Ν,Ν-dimetyloformamid - woda.The method according to the invention consists in diazotizing 3-amino-5-methylisoxazole with a mixture of concentrated sulfuric acid and aqueous sodium (III) nitrate solution, and then the obtained diazonium salt is coupled with N, N-di (2- hydroxyethyl) aniline. The obtained reaction product, after precipitation from the reaction mixture and drying, is purified by crystallization from a mixture of Ν, Ν-dimethylformamide - water.
Sposób według wynalazku umożliwia otrzymanie w prosty i wydajny sposób nowego monomeru o właściwościach nieliniowo- optycznych i fotochromowych.The method according to the invention makes it possible to obtain a new monomer with nonlinear-optical and photochromic properties in a simple and efficient manner.
Przedmiot wynalazku przedstawiony jest w przykładzie wytwarzania monomeru o wzorze przedstawionym na rysunku.The subject of the invention is illustrated in the example for the preparation of a monomer of the formula shown in the drawing.
0,01 mola 3-amino-5-metyloizoksazolu rozpuszcza się w kwasie octowym i dodaje 20 ml stężonego kwasu siarkowego. Następnie porcjami dodaje się 30 ml wodnego roztworu, zawierającego 0,011 mola azotanu sodu (III) (NaNO2), tak aby temperatura mieszaniny reakcyjnej nie wzrosła powyżej 5°C. Całość miesza się za pomocą mieszadła magnetycznego w łaźni lodowej w temperaturze 0-5°C przez 2 godz. Po tym czasie dodaje się 0,01 mola N,N-di(2-hydroksyetylo)aniliny rozpuszczonej w 100 ml metanolu. Całość miesza się przez kilkanaście godzin do temperatury pokojowej. Wytrącony osad odsącza się i suszy. Otrzymany produkt oczyszcza się przez krystalizację z mieszaniny DMF woda. Otrzymany barwny produkt odsącza się i suszy w temperaturze 50-60°C. Wydajność surowego produktu wynosi 67%.0.01 mole of 3-amino-5-methylisoxazole is dissolved in acetic acid and 20 ml of concentrated sulfuric acid are added. Then 30 ml of an aqueous solution containing 0.011 mol of sodium nitrate (NaNO2) are added portionwise so that the temperature of the reaction mixture does not rise above 5 ° C. The mixture is stirred with a magnetic stirrer in an ice bath at 0-5 ° C for 2 hours. After this time, 0.01 mol of N, N-di (2-hydroxyethyl) aniline dissolved in 100 ml of methanol are added. The mixture is stirred for several hours to room temperature. The precipitate formed is filtered off and dried. The product obtained is purified by crystallization from a DMF water mixture. The resulting colored product is filtered off and dried at 50-60 ° C. The yield of the crude product is 67%.
HNMR (rozpuszczalnik DMSO-d6 wzorzec TMS): 2,09 (s, 2H, OH); 2,45 (s, 3H, -CH3 w pierścieniu metyloizoksazolowym); 3,61 (m, 4H, -N-CH2-); 3,89 (m, 4H, -CH2O-); 6,46 (s, 1H w pierścieniu metyloizoksazolowym); 6,93 (d, 2H, protony pierścienia fenylowego w pozycji orto w stosunku do grupy aminowej); 7,78 (d, 2H, protony pierścienia fenylowego w pozycji meta w stosunku do grupy aminowej), Xmax w DMSO wynosi 450 nm.HNMR (DMSO-d6 solvent pattern TMS): 2.09 (s, 2H, OH); 2.45 (s, 3H, -CH3 in the methyl isoxazole ring); 3.61 (m, 4H, -N-CH2-); 3.89 (m, 4H, -CH2O-); 6.46 (s, 1H over the methylisoxazole ring); 6.93 (d, 2H, the phenyl ring protons ortho to the amino group); 7.78 (d, 2H, the phenyl ring protons meta position with respect to the amino group), X max in DMSO is 450 nm.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL380843A PL213577B1 (en) | 2006-10-16 | 2006-10-16 | New non-linear-optical manometer and its production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL380843A PL213577B1 (en) | 2006-10-16 | 2006-10-16 | New non-linear-optical manometer and its production method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL380843A1 PL380843A1 (en) | 2008-04-28 |
| PL213577B1 true PL213577B1 (en) | 2013-03-29 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| PL380843A PL213577B1 (en) | 2006-10-16 | 2006-10-16 | New non-linear-optical manometer and its production method |
Country Status (1)
| Country | Link |
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| PL (1) | PL213577B1 (en) |
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- 2006-10-16 PL PL380843A patent/PL213577B1/en not_active IP Right Cessation
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| Publication number | Publication date |
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| PL380843A1 (en) | 2008-04-28 |
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| Date | Code | Title | Description |
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| LAPS | Decisions on the lapse of the protection rights |
Effective date: 20091016 |