DE3783807T2 - Organisches nicht-lineares optisches material. - Google Patents
Organisches nicht-lineares optisches material.Info
- Publication number
- DE3783807T2 DE3783807T2 DE8787304478T DE3783807T DE3783807T2 DE 3783807 T2 DE3783807 T2 DE 3783807T2 DE 8787304478 T DE8787304478 T DE 8787304478T DE 3783807 T DE3783807 T DE 3783807T DE 3783807 T2 DE3783807 T2 DE 3783807T2
- Authority
- DE
- Germany
- Prior art keywords
- substituent
- nonlinear optical
- optical material
- material according
- organic nonlinear
- 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 - Fee Related
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 112
- 239000000463 material Substances 0.000 title claims abstract description 58
- 125000001424 substituent group Chemical group 0.000 claims abstract description 123
- 239000013078 crystal Substances 0.000 claims abstract description 80
- UVEWQKMPXAHFST-UHFFFAOYSA-N n,1-diphenylmethanimine Chemical class C=1C=CC=CC=1C=NC1=CC=CC=C1 UVEWQKMPXAHFST-UHFFFAOYSA-N 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 19
- 239000004202 carbamide Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 abstract description 13
- 238000002844 melting Methods 0.000 abstract description 12
- 230000008018 melting Effects 0.000 abstract description 12
- 230000003993 interaction Effects 0.000 abstract description 9
- 238000007796 conventional method Methods 0.000 abstract description 7
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 53
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 37
- 239000000243 solution Substances 0.000 description 37
- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 25
- -1 p-nitroaniline Chemical class 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 235000019441 ethanol Nutrition 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 238000010992 reflux Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
- 238000010586 diagram Methods 0.000 description 11
- 238000000921 elemental analysis Methods 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 230000003595 spectral effect Effects 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 6
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 6
- YEKPNMQQSPHKBP-UHFFFAOYSA-N 2-methyl-6-nitrobenzoic anhydride Chemical compound CC1=CC=CC([N+]([O-])=O)=C1C(=O)OC(=O)C1=C(C)C=CC=C1[N+]([O-])=O YEKPNMQQSPHKBP-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000007810 chemical reaction solvent Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 238000012856 packing Methods 0.000 description 5
- 230000004044 response Effects 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000000859 sublimation Methods 0.000 description 4
- 230000008022 sublimation Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005034 decoration Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 230000010287 polarization Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 238000003077 quantum chemistry computational method Methods 0.000 description 3
- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- JTMDQMVSNLXDSI-UHFFFAOYSA-N 2-bromo-n-(2-methoxy-5-nitrophenyl)acetamide Chemical compound COC1=CC=C([N+]([O-])=O)C=C1NC(=O)CBr JTMDQMVSNLXDSI-UHFFFAOYSA-N 0.000 description 2
- GVBXZIANHMNKAK-UHFFFAOYSA-N 2-chloro-4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C(Cl)=C1 GVBXZIANHMNKAK-UHFFFAOYSA-N 0.000 description 2
- FCDAGNIVHLUJRM-UHFFFAOYSA-N 2-chloro-n-(2-methoxy-5-nitrophenyl)acetamide Chemical compound COC1=CC=C([N+]([O-])=O)C=C1NC(=O)CCl FCDAGNIVHLUJRM-UHFFFAOYSA-N 0.000 description 2
- NIPDVSLAMPAWTP-UHFFFAOYSA-N 2-methoxy-5-nitroaniline Chemical compound COC1=CC=C([N+]([O-])=O)C=C1N NIPDVSLAMPAWTP-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
- BNIDBPBBKOFHJO-UHFFFAOYSA-N 4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1.COC1=CC=C(N)C=C1 BNIDBPBBKOFHJO-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000003412 L-alanyl group Chemical group [H]N([H])[C@@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 2
- BSOLAQMZTBVZLA-QMMMGPOBSA-N L-tyrosinyl radical Chemical group OC(=O)[C@@H](N)CC1=CC=C([O])C=C1 BSOLAQMZTBVZLA-QMMMGPOBSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- HCVBBVTZZJFVLA-NSHDSACASA-N [(2s)-1-(4-nitrophenyl)pyrrolidin-2-yl]methanol Chemical compound OC[C@@H]1CCCN1C1=CC=C([N+]([O-])=O)C=C1 HCVBBVTZZJFVLA-NSHDSACASA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 238000000653 depth-selective Mossbauer spectroscopy Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 230000005283 ground state Effects 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- NVLSIZITFJRWPY-ONEGZZNKSA-N n,n-dimethyl-4-[(e)-2-(4-nitrophenyl)ethenyl]aniline Chemical compound C1=CC(N(C)C)=CC=C1\C=C\C1=CC=C([N+]([O-])=O)C=C1 NVLSIZITFJRWPY-ONEGZZNKSA-N 0.000 description 2
- INHNYGHBQGTDTD-UHFFFAOYSA-N n-(5-amino-2-methoxyphenyl)-2-bromoacetamide;hydrochloride Chemical compound Cl.COC1=CC=C(N)C=C1NC(=O)CBr INHNYGHBQGTDTD-UHFFFAOYSA-N 0.000 description 2
- LOBRJRMBSIRDCB-UHFFFAOYSA-N n-(5-amino-2-methoxyphenyl)-2-chloroacetamide;hydrochloride Chemical compound Cl.COC1=CC=C(N)C=C1NC(=O)CCl LOBRJRMBSIRDCB-UHFFFAOYSA-N 0.000 description 2
- TZSQCGFTOHIDIB-UHFFFAOYSA-N n-[2-(dimethylamino)-5-nitrophenyl]acetamide Chemical compound CN(C)C1=CC=C([N+]([O-])=O)C=C1NC(C)=O TZSQCGFTOHIDIB-UHFFFAOYSA-N 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 1
- BZKOZYWGZKRTIB-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-6-amine Chemical compound O1CCOC2=CC(N)=CC=C21 BZKOZYWGZKRTIB-UHFFFAOYSA-N 0.000 description 1
- JQMFQLVAJGZSQS-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JQMFQLVAJGZSQS-UHFFFAOYSA-N 0.000 description 1
- SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 1
- LLYXJBROWQDVMI-UHFFFAOYSA-N 2-chloro-4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1Cl LLYXJBROWQDVMI-UHFFFAOYSA-N 0.000 description 1
- KWIXNFOTNVKIGM-UHFFFAOYSA-N 2-chloro-5-nitroaniline Chemical compound NC1=CC([N+]([O-])=O)=CC=C1Cl KWIXNFOTNVKIGM-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- JDTUPLBMGDDPJS-UHFFFAOYSA-N 2-methoxy-2-phenylethanol Chemical compound COC(CO)C1=CC=CC=C1 JDTUPLBMGDDPJS-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- GWMXUYUAJMDREQ-UHFFFAOYSA-N 4-amino-2-chlorophenol;hydrochloride Chemical compound Cl.NC1=CC=C(O)C(Cl)=C1 GWMXUYUAJMDREQ-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
- WTFUTSCZYYCBAY-SXBRIOAWSA-N 6-[(E)-C-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-N-hydroxycarbonimidoyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C/C(=N/O)/C1=CC2=C(NC(O2)=O)C=C1 WTFUTSCZYYCBAY-SXBRIOAWSA-N 0.000 description 1
- BOFRXDMCQRTGII-UHFFFAOYSA-N 619-08-9 Chemical compound OC1=CC=C([N+]([O-])=O)C=C1Cl BOFRXDMCQRTGII-UHFFFAOYSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical group CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004974 Thermotropic liquid crystal Substances 0.000 description 1
- AJJLBCISIICXMS-UHFFFAOYSA-N [acetyloxy-(6-chloro-6-nitrocyclohexa-2,4-dien-1-yl)methyl] acetate Chemical compound C(C)(=O)OC(C1C(C=CC=C1)([N+](=O)[O-])Cl)OC(C)=O AJJLBCISIICXMS-UHFFFAOYSA-N 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000010365 information processing Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- BUZMXMGVGWIAJH-UHFFFAOYSA-N n-(2-chloro-5-nitrophenyl)acetamide Chemical compound CC(=O)NC1=CC([N+]([O-])=O)=CC=C1Cl BUZMXMGVGWIAJH-UHFFFAOYSA-N 0.000 description 1
- LNEITKYWXMCTLP-UHFFFAOYSA-N n-(2-methoxy-5-nitrophenyl)acetamide Chemical compound COC1=CC=C([N+]([O-])=O)C=C1NC(C)=O LNEITKYWXMCTLP-UHFFFAOYSA-N 0.000 description 1
- SRCVEDBOHDSKPL-UHFFFAOYSA-N n-(5-amino-2-methoxyphenyl)acetamide;hydrochloride Chemical compound Cl.COC1=CC=C(N)C=C1NC(C)=O SRCVEDBOHDSKPL-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 238000007500 overflow downdraw method Methods 0.000 description 1
- 238000001782 photodegradation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004417 unsaturated alkyl group Chemical group 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/35—Non-linear optics
- G02F1/355—Non-linear optics characterised by the materials used
- G02F1/361—Organic materials
- G02F1/3611—Organic materials containing Nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
Landscapes
- Physics & Mathematics (AREA)
- Nonlinear Science (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Optical Fibers, Optical Fiber Cores, And Optical Fiber Bundles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Indole Compounds (AREA)
Claims (31)
1. Organisches nichtlineares optisches Material, welches ein
Benzylidenanilinderivat mit einem Elektronendonor-Substituenten (D) in
4-Stellung, einem Elektronenakzeptor-Substituenten (A) in 4-Stellung und
zumindest einem Substituenten in jeder geeigneten Stellung aufweist, der die
Funktion hat, die Molekülausrichtung im Kristall so zu steuern, daß die
Zentrosymmetrie des Kristalls aufgehoben wird, und mit einer optischen
Nicht-Linearität, die zumindest das 10fache jener von Harnstoff beträgt.
2. Organisches nichtlineares optisches Material nach Anspruch 1, worin
zumindest eines von R&sub1; bis R&sub9; in der folgenden Formel (1) ein Substituent
ist, der die Funktion der Steuerung der Molekülausrichtung im Kristall:
hat, worin D für einen Elektronendonor-Substituenten steht, A für einen
Elektronenakzeptor-Substituenten steht und R&sub1; bis R&sub9; für ein Wasserstoffatom
oder einen wahlweisen Substituenten stehen, worin zumindest eines aus R&sub1; bis
R&sub9; ein die Molekülausrichtung steuernder Substituent ist.
3. Organisches nichtlineares optisches Material nach Anspruch 2, worin die
Wasserlöslichkeit des genannten Materials bei 25ºC geringer als 1,0 · 10&supmin;²
g/100 ml ist.
4. Organisches nichtlineares optisches Material nach Anspruch 2 oder 3, worin
die optische Nicht-Linearität des genannten Materials zumindest das 150fache
jener von Harnstoff beträgt.
5. Organisches nichtlineares optisches Material nach einem der Ansprüche 2
bis 4, worin der die Molekülausrichtung steuernde Substituent in der Formel
(1) ein wasserstoffbindungsbildender Substituent ist.
6. Organisches nichtlineares optisches Material nach einem der Ansprüche 2
bis 5, worin der die Molekülausrichtung steuernde Substituent in der Formel
(1) ein Substituent ist, der eine große sterische Hinderung verursachen kann.
7. Organisches nichtlineares optisches Material nach einem der Ansprüche 2
bis 6, worin die Kombination des Elektronendonor-Substituenten D mit dem
Elektronenakzeptor-Substituenten A eine Kombination aus relativ starken und
schwachen Substituenten ist.
8. Organisches nichtlinears optisches Material nach einem der Ansprüche 2
bis 7, worin der Elektronenakzeptor-Substituent A eine Nitrogruppe ist.
9. Organisches nichtlineares optisches Material nach einem der Ansprüche 2
bis 8, worin der Elektronendonor-Substituent D eine Hydroxylgruppe oder eine
Alkoxygruppe ist.
10. Organisches nichtlineares optisches Material nach Anspruch 2, worin der
Elektronendonor-Substituent D eine Hydroxylgruppe oder eine Alkoxygruppe ist
und der Elektronenakzeptor-Substituent A eine Nitrogruppe ist.
11. Organisches nichtlineares optisches Material nach einem der Ansprüche
2 bis 10, worin R&sub9; in der Formel (1) ein Wasserstoffatom ist.
12. Organisches nichtlinears optisches Material nach Anspruch 11, worin sieben
aus R&sub1; bis R&sub8; in der Formel (1) ebenfalls für ein Wasserstoffatom stehen.
13. Organisches nichtlineares optisches Material nach Anspruch 11, worin R&sub1;
bis R&sub4; und drei aus R&sub5; bis R&sub8; in der Formel (1) ebenfalls für ein
Wasserstoffatom stehen.
14. Organisches nichtlineares optisches Material nach Anspruch 13, worin der
die Molekülausrichtung steuernde Substituent in Orthostellung zum
Elektronendonor-Substituenten D angeordnet ist.
15. Organisches nichtlineares optisches Material nach Anspruch 2, worin der
die Molekülausrichtung steuernde Substituent ein eine Amidbindung enthaltender
Substituent ist.
16. Organisches nichtlineares optisches Material nach Anspruch 2, worin der
die Molekülausrichtung steuernde Substituent ein Halogenatom ist.
17. Organisches nichtlineares optisches Material nach Anspruch 15, worin der
die Molekülausrichtung steuernde, eine Amidbindung enthaltende Substituent
eine Alkanoylaminogruppe ist.
18. Organisches nichtlineares optisches Material nach Anspruch 17, worin die
Alkanoylaminogruppe eine Acetylaminogruppe ist.
19. Organisches nichtlineares optisches Material nach Anspruch 17, worin die
Alkanoylaminogruppe eine Halogenacetylaminogruppe ist.
20. Organisches nichtlineares optisches Material nach Anspruch 2, worin das
Benzylidenanilinderivat 4'-Nitrobenzyliden-3-acetylamino-4-methoxyanilin ist.
21. Organisches nichtlineares optisches Material nach Anspruch 2, worin das
Benzylidenanilinderivat 4'-Nitrobenzyliden-3-bromacetylamino-4-methoxyanilin
ist.
22. Organisches nichtlineares optisches Material nach Anspruch 2, worin das
Benzylidenanilinderivat 4'-Nitrobenzyliden-3-chloracetylamino-4-methoxyanilin
ist.
23. Organisches nichtlineares optisches Material nach Anspruch 2, worin das
Benzylidenanilinderivat 4'-Nitrobenzyliden-3-chlor-4-hydroxyanilin ist.
24. Organisches nichtlineares optisches Material nach Anspruch 2, worin alle
oder ein Teil der Wasserstoffatome des durch die Formel (1) dargestellten
Benzylidenanilinderivats deuterisiert sind.
25. Organisches nichtlineares optisches Material nach Anspruch 1, welches
ein Benzylidenanilinderivat mit einem Elektronendonor-Substituenten mit der
Funktion der Steuerung der Molekülausrichtung im Kristall in Stellung D' in
der folgenden Formel (2) umfaßt und eine optische Nicht-Linearität aufweist,
die zumindest das 10fache der von Harnstoff beträgt:
worin D' für einen Elektronendonor- und die Molekülausrichtung steuernden
Substituenten steht, A für einen Elektronenakzeptor-Srnbstituenten steht und
R&sub1; bis R&sub9; für ein Wasserstoffatom oder einen wahlweisen Substituenten stehen.
26. Organisches nichtlineares optisches Material nach Anspruch 25, worin die
Wasserlöslichkeit bei 25ºC geringer als 1,0 · 10&supmin;² g/100 ml ist.
27. Organisches nichtlineares optisches Material nach Anspruch 25 oder 26,
worin die optische Nicht-Linearität zumindest das 150fache jener von Harnstoff
beträgt.
28. Organisches nichtlineares optisches Material nach einem der Ansprüche
25 bis 27, worin der Elektronendonor- und die Molekülausrichtung steuernde
Substituent (D') eine Alkoxy Gruppe -OR ist, in der R für eine Alkylgruppe,
eine Allylgruppe, eine Arylgruppe, eine Aralkylgruppe oder ein Derivat davon
steht.
29. Organisches nichtlineares optisches Material nach einem der Ansprüche
25 bis 28, worin der Elektronenakzeptor-Substituent (A) eine Nitrogruppe ist.
30. Organisches nichtlineares optisches Material nach Anspruch 25, worin das
Benzylidenanilinderivat 4'-Nitrobenzyliden-3,4-äthylendioxyanilin ist.
31. Organisches nichtlineares optisches Material nach Anspruch 25, worin alle
oder ein Teil der Wasserstoffatome des durch die Formel (2) dargestellten
Benzylidenanilinderivats deuterisiert sind.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11448686 | 1986-05-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3783807D1 DE3783807D1 (de) | 1993-03-11 |
| DE3783807T2 true DE3783807T2 (de) | 1993-06-17 |
Family
ID=14638954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8787304478T Expired - Fee Related DE3783807T2 (de) | 1986-05-21 | 1987-05-20 | Organisches nicht-lineares optisches material. |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4987255A (de) |
| EP (1) | EP0250099B1 (de) |
| JP (1) | JPS63113429A (de) |
| AT (1) | ATE85135T1 (de) |
| DE (1) | DE3783807T2 (de) |
| ES (1) | ES2038661T3 (de) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5169986A (en) * | 1986-05-21 | 1992-12-08 | Toray Industries, Inc. | Organic nonlinear optical material |
| US4970120A (en) * | 1987-07-25 | 1990-11-13 | Hoechst Aktiengesellschaft | Film comprising unimolecular layers |
| JPS6438734A (en) * | 1987-08-05 | 1989-02-09 | Sumitomo Electric Industries | Nonlinear optical material |
| WO1991000544A1 (fr) * | 1989-06-28 | 1991-01-10 | Toray Industries, Inc. | Element optique quadratique non lineaire |
| RU2134259C1 (ru) * | 1997-08-13 | 1999-08-10 | Стерлитамакский нефтехимический завод | N,n-диметиламинометилированные ароматические основания шиффа в качестве ускорителя отверждения эпоксидных смол и способ их получения |
| US6645579B1 (en) * | 1999-11-29 | 2003-11-11 | Canon Kabushiki Kaisha | Liquid crystal device |
| DE20122842U1 (de) | 2001-05-08 | 2008-07-17 | Deutsche Thomson Ohg | Einrichtung zum Verarbeiten von Videobildern |
| US7963287B2 (en) * | 2005-04-28 | 2011-06-21 | Boston Scientific Scimed, Inc. | Tissue-treatment methods |
| US20070142859A1 (en) * | 2005-12-19 | 2007-06-21 | Boston Scientific Scimed, Inc. | Embolic coils |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4420740Y1 (de) * | 1966-06-15 | 1969-09-04 | ||
| JPS4410775Y1 (de) * | 1966-10-17 | 1969-05-01 | ||
| US3592913A (en) * | 1967-05-31 | 1971-07-13 | Sumitomo Chemical Co | Fungicidal method and compositions therefor comprising 2,3,4,5,6-pentachlorobenzylidene-aniline derivatives |
| US3827780A (en) * | 1971-10-14 | 1974-08-06 | Univ Temple | Stable anil-type nematic liquid crystals |
| US4047803A (en) * | 1973-04-24 | 1977-09-13 | Dai Nippon Toryo Kabushiki Kaisha | Nematic liquid crystal compositions |
| CH599333A5 (de) * | 1976-05-04 | 1978-05-31 | Bbc Brown Boveri & Cie | |
| FR2520360A1 (fr) * | 1982-01-26 | 1983-07-29 | Nicoud Jean | Nouveaux derives de la paranitroaniline utilisables en optique non lineaire et en electro-optique et leur procede de preparation |
| US4733109A (en) * | 1986-02-03 | 1988-03-22 | Minnesota Mining And Manufacturing Company | Second harmonic generation with Schiff bases |
-
1987
- 1987-05-19 JP JP62121678A patent/JPS63113429A/ja active Granted
- 1987-05-20 AT AT87304478T patent/ATE85135T1/de not_active IP Right Cessation
- 1987-05-20 ES ES198787304478T patent/ES2038661T3/es not_active Expired - Lifetime
- 1987-05-20 EP EP87304478A patent/EP0250099B1/de not_active Expired - Lifetime
- 1987-05-20 DE DE8787304478T patent/DE3783807T2/de not_active Expired - Fee Related
-
1988
- 1988-07-25 US US07/225,655 patent/US4987255A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0438337B2 (de) | 1992-06-24 |
| EP0250099A3 (en) | 1990-02-14 |
| JPS63113429A (ja) | 1988-05-18 |
| ES2038661T3 (es) | 1993-08-01 |
| US4987255A (en) | 1991-01-22 |
| DE3783807D1 (de) | 1993-03-11 |
| ATE85135T1 (de) | 1993-02-15 |
| EP0250099A2 (de) | 1987-12-23 |
| EP0250099B1 (de) | 1993-01-27 |
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| 8364 | No opposition during term of opposition | ||
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