NO872039L - Nitrogenholdige heterocykliske forbindelser. - Google Patents
Nitrogenholdige heterocykliske forbindelser.Info
- Publication number
- NO872039L NO872039L NO872039A NO872039A NO872039L NO 872039 L NO872039 L NO 872039L NO 872039 A NO872039 A NO 872039A NO 872039 A NO872039 A NO 872039A NO 872039 L NO872039 L NO 872039L
- Authority
- NO
- Norway
- Prior art keywords
- cyano
- cis
- cyclohexane
- phenyl
- ester
- Prior art date
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 36
- -1 biphenylyl Chemical group 0.000 claims description 23
- 239000004990 Smectic liquid crystal Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000004955 1,4-cyclohexylene group Chemical class [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 6
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000012071 phase Substances 0.000 description 49
- 239000000203 mixture Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 230000010287 polarization Effects 0.000 description 6
- 230000002269 spontaneous effect Effects 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- KQDQEDGPZKEHMH-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-butoxypyrimidin-2-yl)benzoate Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(OCCCC)=CN=2)C=C1 KQDQEDGPZKEHMH-UHFFFAOYSA-N 0.000 description 1
- OTXGJXSAPGNWQC-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-decoxypyrimidin-2-yl)benzoate Chemical compound N1=CC(OCCCCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 OTXGJXSAPGNWQC-UHFFFAOYSA-N 0.000 description 1
- KBJZHEXPTSMENQ-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-heptoxypyridin-2-yl)benzoate Chemical compound N1=CC(OCCCCCCC)=CC=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 KBJZHEXPTSMENQ-UHFFFAOYSA-N 0.000 description 1
- KMRSRDRDLDLNPG-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-heptoxypyrimidin-2-yl)benzoate Chemical compound N1=CC(OCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 KMRSRDRDLDLNPG-UHFFFAOYSA-N 0.000 description 1
- XMGXEUUNKRFEDG-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-hexoxypyridin-2-yl)benzoate Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(OCCCCCC)=CC=2)C=C1 XMGXEUUNKRFEDG-UHFFFAOYSA-N 0.000 description 1
- GWRJGKNKBYMRAI-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-hexoxypyrimidin-2-yl)benzoate Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(OCCCCCC)=CN=2)C=C1 GWRJGKNKBYMRAI-UHFFFAOYSA-N 0.000 description 1
- STRLIZRTQMIALP-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-nonoxypyrimidin-2-yl)benzoate Chemical compound N1=CC(OCCCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 STRLIZRTQMIALP-UHFFFAOYSA-N 0.000 description 1
- DVTMUCVVXCVVLT-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-octoxypyridin-2-yl)benzoate Chemical compound N1=CC(OCCCCCCCC)=CC=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 DVTMUCVVXCVVLT-UHFFFAOYSA-N 0.000 description 1
- CVEMWLFBFXZQGX-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-pentoxypyridin-2-yl)benzoate Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(OCCCCC)=CC=2)C=C1 CVEMWLFBFXZQGX-UHFFFAOYSA-N 0.000 description 1
- JDTITCZSRLYJGI-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-pentoxypyrimidin-2-yl)benzoate Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(OCCCCC)=CN=2)C=C1 JDTITCZSRLYJGI-UHFFFAOYSA-N 0.000 description 1
- GWCGGAJXRWVMFZ-UHFFFAOYSA-N (4-cyano-4-heptylcyclohexyl) 4-(5-propylpyrimidin-2-yl)benzoate Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCC)=CN=2)C=C1 GWCGGAJXRWVMFZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- KRUVEFPHPNUUQC-UHFFFAOYSA-N 1-heptyl-4-(iodomethyl)cyclohexane-1-carbonitrile Chemical compound CCCCCCCC1(C#N)CCC(CI)CC1 KRUVEFPHPNUUQC-UHFFFAOYSA-N 0.000 description 1
- BWSJCIQVGWVVPG-UHFFFAOYSA-N 2-(ethoxymethylidene)heptanal Chemical compound CCCCCC(C=O)=COCC BWSJCIQVGWVVPG-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- TWLNIMGLDJVXLL-UHFFFAOYSA-N 4-(4-cyano-4-hexylcyclohexyl)benzenecarboximidamide;hydrochloride Chemical compound Cl.C1CC(CCCCCC)(C#N)CCC1C1=CC=C(C(N)=N)C=C1 TWLNIMGLDJVXLL-UHFFFAOYSA-N 0.000 description 1
- RFJRBHWPACFFMC-UHFFFAOYSA-N 4-(5-hexylpyrimidin-2-yl)phenol Chemical compound N1=CC(CCCCCC)=CN=C1C1=CC=C(O)C=C1 RFJRBHWPACFFMC-UHFFFAOYSA-N 0.000 description 1
- ZUEPHMIGLCURNA-UHFFFAOYSA-N 4-[[(4-cyanophenyl)-[4-(5-nonylpyrimidin-2-yl)phenyl]methoxy]-[4-(5-nonylpyrimidin-2-yl)phenyl]methyl]benzonitrile Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(C(OC(C=2C=CC(=CC=2)C#N)C=2C=CC(=CC=2)C=2N=CC(CCCCCCCCC)=CN=2)C=2C=CC(=CC=2)C#N)C=C1 ZUEPHMIGLCURNA-UHFFFAOYSA-N 0.000 description 1
- VTIPXAAINIQCCN-UHFFFAOYSA-N 4-cyano-4-heptylcyclohexane-1-carboxylic acid Chemical compound CCCCCCCC1(C#N)CCC(C(O)=O)CC1 VTIPXAAINIQCCN-UHFFFAOYSA-N 0.000 description 1
- KJZWYCAIEUYAIW-UHFFFAOYSA-N 4-cyanocyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(C#N)CC1 KJZWYCAIEUYAIW-UHFFFAOYSA-N 0.000 description 1
- XXOUHKWIQVEQIH-UHFFFAOYSA-N 5-butoxypyridine-2-carboxylic acid Chemical compound CCCCOC1=CC=C(C(O)=O)N=C1 XXOUHKWIQVEQIH-UHFFFAOYSA-N 0.000 description 1
- JDGWQKJGGFDZIM-UHFFFAOYSA-N 5-decoxypyridine-2-carboxylic acid Chemical compound CCCCCCCCCCOC1=CC=C(C(O)=O)N=C1 JDGWQKJGGFDZIM-UHFFFAOYSA-N 0.000 description 1
- BHBVZTPSMXMHTQ-UHFFFAOYSA-N 5-heptoxypyridine-2-carboxylic acid Chemical compound CCCCCCCOC1=CC=C(C(O)=O)N=C1 BHBVZTPSMXMHTQ-UHFFFAOYSA-N 0.000 description 1
- DUKKMMYQNBPJKS-UHFFFAOYSA-N 5-heptyl-2-(4-methoxyphenyl)pyridine Chemical compound N1=CC(CCCCCCC)=CC=C1C1=CC=C(OC)C=C1 DUKKMMYQNBPJKS-UHFFFAOYSA-N 0.000 description 1
- FWUKUCZPNKFOKT-UHFFFAOYSA-N 5-heptyl-2-[4-[[[4-(5-heptylpyrimidin-2-yl)phenyl]-(4-hexylphenyl)methoxy]-(4-hexylphenyl)methyl]phenyl]pyrimidine Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C(OC(C=2C=CC(CCCCCC)=CC=2)C=2C=CC(=CC=2)C=2N=CC(CCCCCCC)=CN=2)C=2C=CC(CCCCCC)=CC=2)C=C1 FWUKUCZPNKFOKT-UHFFFAOYSA-N 0.000 description 1
- ZQTCISOMXPYKMJ-UHFFFAOYSA-N 5-hexoxypyridine-2-carboxylic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)N=C1 ZQTCISOMXPYKMJ-UHFFFAOYSA-N 0.000 description 1
- IEOSDPQVDNLLKP-UHFFFAOYSA-N 5-hexyl-2-[4-[[[4-(5-hexylpyrimidin-2-yl)phenyl]-(4-pentylphenyl)methoxy]-(4-pentylphenyl)methyl]phenyl]pyrimidine Chemical compound N1=CC(CCCCCC)=CN=C1C1=CC=C(C(OC(C=2C=CC(CCCCC)=CC=2)C=2C=CC(=CC=2)C=2N=CC(CCCCCC)=CN=2)C=2C=CC(CCCCC)=CC=2)C=C1 IEOSDPQVDNLLKP-UHFFFAOYSA-N 0.000 description 1
- LRVWMFHQTPNPJY-UHFFFAOYSA-N 5-hexylpyridine-2-carboxylic acid Chemical compound CCCCCCC1=CC=C(C(O)=O)N=C1 LRVWMFHQTPNPJY-UHFFFAOYSA-N 0.000 description 1
- REUXMHILPWSNAZ-UHFFFAOYSA-N 5-nonoxypyridine-2-carboxylic acid Chemical compound CCCCCCCCCOC1=CC=C(C(O)=O)N=C1 REUXMHILPWSNAZ-UHFFFAOYSA-N 0.000 description 1
- UQIHAPCKXFURLU-UHFFFAOYSA-N 5-nonyl-2-[4-[[[4-(5-nonylpyrimidin-2-yl)phenyl]-(4-propylphenyl)methoxy]-(4-propylphenyl)methyl]phenyl]pyrimidine Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(C(OC(C=2C=CC(CCC)=CC=2)C=2C=CC(=CC=2)C=2N=CC(CCCCCCCCC)=CN=2)C=2C=CC(CCC)=CC=2)C=C1 UQIHAPCKXFURLU-UHFFFAOYSA-N 0.000 description 1
- TYFOIKIYYXHTOV-UHFFFAOYSA-N 5-octoxypyridine-2-carboxylic acid Chemical compound CCCCCCCCOC1=CC=C(C(O)=O)N=C1 TYFOIKIYYXHTOV-UHFFFAOYSA-N 0.000 description 1
- DPCYKLNMNFPPKK-UHFFFAOYSA-N 5-pentoxypyridine-2-carboxylic acid Chemical compound CCCCCOC1=CC=C(C(O)=O)N=C1 DPCYKLNMNFPPKK-UHFFFAOYSA-N 0.000 description 1
- BOHRWPVFCVAKKS-UHFFFAOYSA-N 5-pentylpyridine-2-carboxylic acid Chemical compound CCCCCC1=CC=C(C(O)=O)N=C1 BOHRWPVFCVAKKS-UHFFFAOYSA-N 0.000 description 1
- RAQLHHNBGLJEAK-UHFFFAOYSA-N 5-propyl-2-pyridinecarboxylic acid Chemical compound CCCC1=CC=C(C(O)=O)N=C1 RAQLHHNBGLJEAK-UHFFFAOYSA-N 0.000 description 1
- KYZLWBKEIIMVQV-UHFFFAOYSA-N 6-butoxypyridine-3-carboxylic acid Chemical compound CCCCOC1=CC=C(C(O)=O)C=N1 KYZLWBKEIIMVQV-UHFFFAOYSA-N 0.000 description 1
- QKXKSQXNSFZTLA-UHFFFAOYSA-N 6-heptoxypyridine-3-carboxylic acid Chemical compound CCCCCCCOC1=CC=C(C(O)=O)C=N1 QKXKSQXNSFZTLA-UHFFFAOYSA-N 0.000 description 1
- KJWAYJXNAIDFNV-UHFFFAOYSA-N 6-hexoxypyridine-3-carboxylic acid Chemical compound CCCCCCOC1=CC=C(C(O)=O)C=N1 KJWAYJXNAIDFNV-UHFFFAOYSA-N 0.000 description 1
- YXVRTHPEKWLVJI-UHFFFAOYSA-N 6-nonoxypyridine-3-carboxylic acid Chemical compound CCCCCCCCCOC1=CC=C(C(O)=O)C=N1 YXVRTHPEKWLVJI-UHFFFAOYSA-N 0.000 description 1
- YJRUFYZSTYLKOR-UHFFFAOYSA-N 6-nonylpyridine-3-carboxylic acid Chemical compound CCCCCCCCCC1=CC=C(C(O)=O)C=N1 YJRUFYZSTYLKOR-UHFFFAOYSA-N 0.000 description 1
- QJVMDTYBBWGZLQ-UHFFFAOYSA-N 6-octoxypyridine-3-carboxylic acid Chemical compound CCCCCCCCOC1=CC=C(C(O)=O)C=N1 QJVMDTYBBWGZLQ-UHFFFAOYSA-N 0.000 description 1
- RARWYXSDTKTTAU-UHFFFAOYSA-N 6-pentoxypyridine-3-carboxylic acid Chemical compound CCCCCOC1=CC=C(C(O)=O)C=N1 RARWYXSDTKTTAU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- MISUIWKANNDPPL-AQYVVDRMSA-N C1=CC(CCCCCCC)=CC=C1C1=CN=C([C@@H]2CC[C@H](CC2)C#N)N=C1 Chemical compound C1=CC(CCCCCCC)=CC=C1C1=CN=C([C@@H]2CC[C@H](CC2)C#N)N=C1 MISUIWKANNDPPL-AQYVVDRMSA-N 0.000 description 1
- CTLMPSCHACFQQF-UHFFFAOYSA-N C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCC)=CN=2)C=C1 Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCC)=CN=2)C=C1 CTLMPSCHACFQQF-UHFFFAOYSA-N 0.000 description 1
- NTQZLBKLTIBLDQ-UHFFFAOYSA-N C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCC)=CC=2)C=C1 Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCC)=CC=2)C=C1 NTQZLBKLTIBLDQ-UHFFFAOYSA-N 0.000 description 1
- KNUZFPACILFMSY-UHFFFAOYSA-N C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCC)=CN=2)C=C1 Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCC)=CN=2)C=C1 KNUZFPACILFMSY-UHFFFAOYSA-N 0.000 description 1
- QWIRKOISOKYTBS-UHFFFAOYSA-N C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCCC)=CC=2)C=C1 Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCCC)=CC=2)C=C1 QWIRKOISOKYTBS-UHFFFAOYSA-N 0.000 description 1
- XKPYDCLBMAJDAP-UHFFFAOYSA-N C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCCC)=CN=2)C=C1 Chemical compound C1CC(CCCCCCC)(C#N)CCC1OC(=O)C1=CC=C(C=2N=CC(CCCCCC)=CN=2)C=C1 XKPYDCLBMAJDAP-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- DGMPVYSXXIOGJY-UHFFFAOYSA-N Fusaric acid Chemical compound CCCCC1=CC=C(C(O)=O)N=C1 DGMPVYSXXIOGJY-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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- IHSRFCVMRMPZGC-UHFFFAOYSA-N N1=CC(CCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 IHSRFCVMRMPZGC-UHFFFAOYSA-N 0.000 description 1
- ZZBIREGOWWUZBT-UHFFFAOYSA-N N1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 Chemical compound N1=CC(CCCCCCCC)=CC=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 ZZBIREGOWWUZBT-UHFFFAOYSA-N 0.000 description 1
- AIEAHMWNQZPSRU-UHFFFAOYSA-N N1=CC(CCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 Chemical compound N1=CC(CCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 AIEAHMWNQZPSRU-UHFFFAOYSA-N 0.000 description 1
- NEPZDBQTTBKDJO-UHFFFAOYSA-N N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 Chemical compound N1=CC(CCCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 NEPZDBQTTBKDJO-UHFFFAOYSA-N 0.000 description 1
- WNBUFVVGENCYFE-UHFFFAOYSA-N N1=CC(CCCCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 Chemical compound N1=CC(CCCCCCCCCC)=CN=C1C1=CC=C(C(=O)OC2CCC(CCCCCCC)(CC2)C#N)C=C1 WNBUFVVGENCYFE-UHFFFAOYSA-N 0.000 description 1
- 239000004988 Nematic liquid crystal Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JZFVMTKUEHVOSZ-UHFFFAOYSA-N chembl1536636 Chemical compound N1=CC(CCCCCCC)=CC=C1C1=CC=C(O)C=C1 JZFVMTKUEHVOSZ-UHFFFAOYSA-N 0.000 description 1
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- BBBQVCMVHFUKMI-UHFFFAOYSA-N ethyl 4-cyano-4-heptylcyclohexane-1-carboxylate Chemical compound CCCCCCCC1(C#N)CCC(C(=O)OCC)CC1 BBBQVCMVHFUKMI-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- DWNRISLZVCBTRN-UHFFFAOYSA-N lithium;piperidin-1-ide Chemical compound [Li]N1CCCCC1 DWNRISLZVCBTRN-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
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- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3066—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers
- C09K19/3068—Cyclohexane rings in which the rings are linked by a chain containing carbon and oxygen atoms, e.g. esters or ethers chain containing -COO- or -OCO- groups
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
-
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3452—Pyrazine
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3455—Pyridazine
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- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
- C09K19/345—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing two nitrogen atoms
- C09K19/3458—Uncondensed pyrimidines
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- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/325—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a tetrahydronaphthalene, e.g. -2,6-diyl (tetralin)
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K19/322—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring
- C09K2019/326—Compounds containing a naphthalene ring or a completely or partially hydrogenated naphthalene ring containing a decahydronaphthalene, e.g. -2,6-diyl (decalin)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Liquid Crystal Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Foreliggende oppfinnelse angår nitrogenholdige, heterocykliske forbindelser av formel II
hvori
1 2
R og R betegner en alkylgruppe med 1 til 15 C-atomer,
hvori også én eller flere CE^-grupper kan være erstattet med en gruppering valgt fra gruppen -0-, -S-, -CO-, -0-CO-, -0-COO-, -CO-0-, -CH=CH-, -CH-halogen og -CHCN-, eller også av en kombinasjon av to egnede grupperinger, hvorved to heteroatomer ikke direkte er forbundet med hverandre,
m er 0 eller 1,
Ar betegner 1,4-fenylen, 4,4'-bifenylyl eller 2,6-nafthylen,
hvorved én eller flere CH-grupper kan være erstattet med
N,
Z betegner -CO-0-, -0-CO-, -CH20-, -OCH2~, -CH2CH2-,
-CH2CHCN-, -CHCNCH2-, -CH=CH eller en enkeltbinding, og A betegner usubstituert eller i 1- eller 4-stilling CN-sub-
stituert 1,4-cyclohexylen,
med det forbehold at i det tilfellet A = usubstituert 1,4-cyclohexylen, betegner Z -CHCNCH„- eller -CH-CHCN-, og/eller
12
i det minste en CH2-gruppe i mxnst en av restene R og R er erstattet med -CHCN-,
deres anvendelse som komponenter av smektiske, flytende-krystallinske faser, såvel som smektiske, flytendekrystallinske faser, i særdeleshet chirale, skråttstilte, smektiske faser inneholdende forbindelsene av formel I.
Chirale, skråttstilte, smektiske, flytendekrystallinske
faser med ferroelektriske egenskaper kan fremstilles ved at basisblandinger med én eller flere skråttstilte, smektiske faser tilsettes et egnet, chiralt dopestoff (L.A. Beresnev et al., Mol. Cryst. Liq. Cryst. 8_9, 327 (1982);
H.R. Brand et al., J. Physique 4_4, (lett.), L-771 (1983).
Slike faser kan benyttes som dielektrika for hurtig omkoblede displayer som er basert på det av Clark og Lagerwall- be-skrevne prinsipp for SSFLC-teknologi (N.A. Clark og S.T. Lagerwall, Appl. Phys. Lett. 36.'899 (1980); USP 4 367 924) på grunn-lag av de ferroelektriske egenskaper til den chiralt skråttstilte fase. I denne fase er de langstrakte molekyler anordnet i skikt, idet molekylene oppviser en skråstillings- eller vippevinkel i forhold til skiktnormalen. Ved fremadskridende bevegelse fra skikt til skikt endres skråstillingsretningen med en liten vinkel i forhold til en loddrett, på skiktene stående akse slik at det utvikler seg en helix- eller skrue-linjestruktur. I displayer som er basert på prinsippet for SSFLC-teknologi, er de smektiske skikt anordnet loddrett på cellens plater. Den skruelinjelignende anordning av molekylenes skråstillingsretninger undertrykkes på grunn av en meget liten avstand mellom platene (ca. 1-2 um). Derved tvinges molekylenes lengdeakser til å anordne seg i et plan parallelt med cellens plater slik at det oppstår to utmerkede skråstill-ingsorienteringer. Ved hjelp av påtrykning av et passende, elektrisk vekselfelt kan det i den flytende-krystallinske fase som oppviser en spontan polarisasjon, koples frem og tilbake mellom disse tilstander. Dette koplingsforløp er vesentlig raskere enn ved tradisjonelle, skrudde celler (TN-LCD-enheter) som er basert på nematiske flytende krystaller.
En stor ulempe for flere anvendelser av de nåværende tilgjengelige materialer med chiralt skråstilte, smektiske faser (slik som f.eks. Sc<*>) er at den dielektriske anisotropi-verdi er større enn null, eller så fremt den er negativ, bare utviser en verdi som er litt forskjellig fra null. Negativ verdi for den dielektriske anisotropi er nødvendig såfremt den nødvendige planare orientering bevirkes ved overlagring av styrefeltet med et AC-holdefelt med liten amplitude
(J.M. Geary, SID-Tagung, Orlando/Florida, april/mai 1985, foredrag 8.3). Anvendelse av materialer med sterk negativ dielektrisk anisoptropi fører for det meste til en sterk ned-settelse av spontanpolarisasjonen og/eller ugunstige verdier for helningsvinkelen (pitch) og/eller skråstillingen (tilt).
Enn videre innsnevres for det meste temperaturområdet for
de ferroelektriske faser på ugunstig måte.
Det er nå funnet at anvendelse av forbindelsene av formel II som komponenter av chirale, skråttstilte, smektiske blandinger kan redusere de omtalte ulemper vesentlig. Forbindelsene av formel II er således ypperlig egnet som komponenter av chirale, skråttstilte, smektiske, flytende-krystallinske faser. I særdeleshet kan det med deres hjelp fremstilles kjemisk særlig stabile, chirale, skråttstilte, smektiske, flytende-krystallinske faser med gunstig ferroelektrisk faseområde, i særdeleshet med bredt Sc<*>faseområde, negativ dielektrisk anisotropi, gunstig pitchhøyde og høye verdier for den spontane polarisasjon for slike faser. P er den spontane
2
polarisasjon i nC/cm .
Forbindelsene av formel II utviser et bredt anvend-elsesområde. Avhengig av valget av substituentene kan disse forbindelser tjene som basismaterialer av hvilke flytende-krystallinske, smektiske faser i overveiende grad er sammen-satt av, men forbindelsene av formel II kan imidlertid også tilsettes flytende-krystallinske basismaterialer av andre for-bindelsesklasser for eksempelvis å variere den dielektriske og/eller optiske anisotropi og/eller viskositeten og/eller den spontane polarisasjon og/eller faseområde og/eller skrå-stillingsvinkel og/eller hellingsvinkel av et slikt dielektrikum. Gjenstand for oppfinnelsen er således forbindelsene av formel II såvel som deres anvendelse som komponenter (chirale, skråttstilte) smektiske, flytende-krystallinske faser. Gjenstand for oppfinnelsen er enn videre smektiske, flytende-krystallinske faser, i særdeleshet chirale, skråttstilte, smektiske faser, med et innhold av minst én forbindelse av formel II, såvel som flytende-krystallinske tegnelementer, i særdeleshet elektrooptiske tegnelementer som inneholder slike faser.
Forbindelsene av formel II kan ha rettkjedede eller forgrenede vingegrupper R 1 og/eller R 2. Forbindelser med forgrenede vingegrupper kan anvendes i form av racematet eller som optisk aktive forbindelser. Achirale basisblandinger fra forbindelsene av formel II og eventuelt ytterligere achirale komponenter kan dopes med chirale forbindelser av formel II eller også med andre chirale forbindelser for å oppnå chirale, skråttstilte, smektiske faser.
Forbindelsene av formel II inneholder fortrinnsvis en gruppe av formel (A)
eller dens speilbilde i den angitte konfigurasjon med aksial nitrilgruppe og trans-stilling av substituenten. I forbindelsene av de foregående og etterfølgende formler betegner R 1 og R 2 fortrinnsvis R-, R-0-, R-0-CO-, R-O-COO- eller R-CO-0. R er fortrinnsvis en alkylgruppe med fortrinnsvis 5 til 12 C-atomer hvori også en eller to ikke endestående CB^-grupper kan være erstattet med -0-, -0-CO-, -CHCN-, -CH-halogen, -CHCH3"0-, -CHhalogen-COO-, -CHCN-COO-og/eller -CH=CH-. R betegner eksempelvis fortrinnsvis pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl eller dodecyl, men også methyl, ethyl, propyl, butyl, 2-, 3- eller 4-oxapentyl, 2-, 3-, 4- eller 5-oxahexyl, 2-, 3-, 4-, 5-eller 6-oxaheptyl, 2-, 3-, 4-, 5-, 6- eller 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- eller 8-oxanonyl, 2-, 3-, 4-, 5-, 6-, 7-, 8- eller 9-oxadecyl, 1,3-dioxabuty1 (= methoxymethoxy), 1,3-, 1,4- eller 2,4-dioxapentyl, 1,3-, 1,4-, 1,5-, 2,4-, 2,5-eller 3,5-dioxahexy1, 1,3-, 1,4-, 1,5-, 1,6-, 2,4-, 2,5-, 2,6-, 3,5-, 3,6- eller 4,6-dioxahepty1, 1,4-dioxaocty1, 1,4,7-trioxaoctyl, 1,4-dioxanony1, 1,4-dioxadecyl.
Forbindelsene av formel II såvel som de foregående og etterfølgende delformler med forgrenede vingegrupper R"<*>" hhv. R 2 kan leilighetsvis på grunn av en bedre løselighet i de vanlige flytende-krystallinske basismaterialer være av betyd-ning, i særdeleshet imidlertid som chirale dopestoffer for chirale, skråttstilte, smektiske faser, når de er optisk aktive. Slike forbindelser egner seg imidlertid også som komponenter av nematiske flytende-krystallinske faser, i sær deleshet for å nedsette motsatt dreining. Forgrenede grupper av denne type inneholder som regel en eller to kjedeforgren-inger. Fortrinnsvis er det asymmetriske carbonatom forbundet med to forskjellige substituerte C-atomer, et H-atom og en substituent valgt fra gruppen halogen (i særdeleshet F, Cl eller Br), alkyl eller alkoxy med 1-5 C-atomer og CN. Den
1 2 optisk aktive organiske rest R hhv. R har fortrinnsvis formelen
hvori
X betegner -CO-0-, -0-CO-, -0-CO-O-, -CO-, -0-, -S-, -CH=CH-,
-CH=CH-C00- eller en enkeltbinding,
Q betegner alkylen med 1 til 5 C-atomer, hvori også en ikke med X forbundet Cl^-gruppe kan være erstattet med -0-, -CO-,
-0-CO-, -CO-0- eller -CH=CH-, eller en enkeltbinding,
Y betegner CN, halogen, methyl eller methoxy, og
R betegner en fra Y forskjellig alkylgruppe med 1 til 18 C-atomer, hvori også en eller to ikke-tilstøtende Cf^-grupper kan være erstattet med -0-, -CO-, -0-CO-, -CO-0- og/eller
-CH=CH-.
X er fortrinnsvis -CO-0-, -0-CO-, -CH=CH-C00- (trans) eller en enkeltbinding. Særlig foretrukket er -CO-0- og -0-C0-.
Q er fortrinnsvis - CU.^-, -Cf^Cf^- eller en enkeltbinding, og særlig foretrukket en enkeltbinding.
Y er fortrinnsvis CH^, -CN eller Cl, i særdeleshet -CN.
R er fortrinnsvis rettkjedet alkyl med 1 til 10, i særdeleshet 1 til 7, C-atomer.
Foretrukne, forgrenede rester er isopropyl, 2-butyl
(= 1-methylpropyl), isobutyl (= 2-methylpropyl, isobutyl (= 2-methylpropyl), 2-methylbutyl, isopentyl {- 3-methylbutyl), 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, 2-octyl, isopropoxy, 2-methylpropoxy, 2-methylbutoxy, 3-methylbutoxy, 2-methylpentoxy, 3-methylpentoxy,
2-ethylhexoxy, 1-methylhexoxy, 1-methylheptoxy, 2-oxa-3-methylbutyl, 3-oxa-4-methylpenty1, 2-octyloxy, 2-klorpro-pionyloxy, 2-klor-3-methylbutyryloxy, 2-klor-4-methylvalery1-oxy, 2-klor-3-methylvaleryloxy, 2-methyl-3-oxa-pentyl, 2-methy1-3-oxa-hexyl.
Z er fortrinnsvis -CO-0-, -0-CO-, -CH20-, -0-CH2~,
-CH2CH2~eller en enkeltbinding. A er fortrinnsvis i 1- eller 4-stilling med CN-substituert 1,4-cyclohexylen, og særlig foretrukket er Z-A-R<2>, en gruppe av formel
R 2er fortrinnsvis rettkjedet alkyl eller forgrenet alkyl, hvori en eller to CH2~grupper kan være erstattet med -CHCH^-, med fortrinnsvis 2 til 10 C-atomer. Såfremt A betegner usubstituert 1,4-cyclohexylen (fortrinnsvis trans-1,4-cyclohexylen), er Z fortrinnsvis -CH2~CHCN- eller R 2er i særdeleshet en alkylgruppe med 2 til 15 C-atomer, hvori en CH„-gruppe er erstattet med -CHCN-. I dette tilfelle er R 2 fortri.nnsvis en gruppe av formel -(CH^ „) p-CHCN-alkyl, hvori p er 0, 1 eller 2 og alkyl er en rettkjedet alkylgruppe med (14-p) C-atomer.
Blant forbindelsene av formel II såvel som de foregående og etterfølgende delformler er slike foretrukne hvori minst én av de deri inneholdte rester har en av de angitte foretrukne betydninger.
Forbindelsene av formel II utviser en høy kjemisk sta-bilitet. De er fargeløse og godt blandbare med alle anvend-bare flytende krystaller. Deres anvendelse i flytende-krystallinske faser fører til bredere mesofaseområde og for-bedrede verdier for spontanpolarisasjon i chirale, skråttstilte, smektiske faser. Fasene ifølge oppfinnelsen egner seg således meget godt til flytende-krystallinske faser for displayer som beror på prinsippet for SSFLC-teknologi. Enn videre egner de seg imidlertid også for andre elektrooptiske tegnanordninger slik som f.eks. TN-celler eller Guest-Host-celler. Her tjener de ved siden av utvidelsen av mesofaseområdet, i særdeleshet til innstilling av negative verdier for den dielektriske anisotropi, og for forbedring av de elastiske konstanter.
Ar er fortrinnsvis en gruppe av formel a til j:
Gruppene av formel a, b, c, e, f, gogher foretrukne. Særlig foretrukket er e og f.
Forbindelsene av formel II kan eksempelvis erholdes ved omsetning av de tilsvarende cyclohexancarbonitriler (formel II, R 2=H) med et halogenid av formel R 2-halogen.
Nitrilet overføres hensiktsmessig først med en sterk base slik som NaH, NaNE^, lithiumdiisopropylamid, -piperidid eller -2,5-diisopropylpiperidid eller K-tert.-butylat i det tilsvarende carbanion, fortrinnsvis i et inert løsningsmiddel, eksempelvis et hydrocarbon slik som toluen, en ether slik som THF eller dioxan, et amid slik som DMF, et sulfoxyd slik som dimethylsulfoxyd eller en blanding av slike løsningsmidler. Etter tilsetning av R 2-halogen opprettholdes reaksjonsblandingen hensiktsmessig i 1/2 til 16 timer ved temperaturer mellom 0 og 150°C.
Halogenidene kan eksempelvis erholdes fra de tilsvarende alkoholer. Halogen er fortrinnsvis brom eller jod.
Fasene ifølge oppfinnelsen inneholder fortrinnsvis minst tre, i særdeleshet minst fem forbindelser av -formel II. Særlig foretrukket er chirale, skråttstilte, smektiske, flytende-krystallinske faser ifølge oppfinnelsen hvis achirale basisblanding ved siden av forbindelsene av formel II minst inneholder én annen komponent med negativ eller forholdsvis mindre positiv dielektrisk anisotropi. Disse ytterligere komponenter av den chirale basisblanding kan utgjøre 1 til 50%, fortrinnsvis 10 til 25% av basisblandingen. Som ytterligere komponenter med forholdsvis mindre positiv eller negativ dielektrisk anisotropi egner seg forbindelser av delformel Va til Vp:
Fasene ifølge oppfinnelsen inneholder fortrinnsvis minst tre, i særdeleshet minst fem forbindelser av -formel II. Særlig foretrukket er chirale, skråttstilte, smektiske, flytende-krystallinske faser ifølge oppfinnelsen hvis achirale basisblanding ved siden av forbindelsene av formel II minst inneholder én annen komponent med negativ eller forholdsvis mindre positiv dielektrisk anisotropi. Disse ytterligere komponenter av den chirale basisblanding kan utgjøre 1 til 50%, fortrinnsvis 10 til 25% av basisblandingen. Som ytterligere komponenter med forholdsvis mindre positiv eller negativ dielektrisk anisotropi egner seg forbindelser av delformel Va til Vp:
4 5
R og R er fortrinnsvis rettkjedet alkyl, alkoxy, alkanoyloxy eller alkoxycarbony1 med 3 til 12 C-atomer.
X er fortrinnsvis 0. n er 0 eller 1.
Særlig foretrukket er forbindelsene av delformel Va,
4 5
Vb, Vd og Vf, hvori R og R betegner rettkjedet alkyl eller alkoxy med 5 til 10 C-atomer.
Forbindelsene av delformel Vc, Vh og Vi egner seg som tilsetning for smeltepunktnedsettelse og tilsettes normalt basisblandingene i ikke mer enn 5%, fortrinnsvis 1 til 3%.
4 5
R og R betegner i forbindelsene av delformel Vc, Vh og Vi fortrinnsvis rettkjedet alkyl med 2 til 7, fortrinnsvis 3 til 5, C-atomer. En ytterligere forbindelsesklasse som er egnet for smeltepunktnedsettelse i fasene ifølge oppfinnelsen, er slike av formel
hvori R 4 og R 5 har de for Vc, Vh og Vi angitte foretrukne betydninger .
Som ytterligere komponenter med negativ dielektrisk anisotropi egner seg enn videre forbindelser inneholdende strukturelementet B eller C.
Foretrukne forbindelser av denne type tilsvarer formel VIb og VIc:
R' og R' ' betegner fortrinnsvis rettkjedede alkyl- eller 1 2
alkoxygrupper med 2 til 10 C-atomer. Q og Q betegner 1,4-fenylen, trans-1,4-cyclohexylen, 4,4<1->bifenylyl, 4-(trans-4-cyclohexyl)-fenyl, trans,trans-4,4<1->bicyclohexyl eller en av
1 2
gruppene Q og Q kan også betegne en enkeltbinding.
Q 3 og Q 4 betegner 1,4-fenylen, 4,4<1->bifenylyl eller
trans-1,4-cyclohexylen. En av gruppene Q 3 og Q 4 kan også betegne 1,4-fenylen hvori minst én CH-gruppe er erstattet med N. R''' er en optisk aktiv rest med et asymmetrisk carbonatom av
struktur
eller Særlig foretrukne forbindelser av formel VIc er slike av formel VIc<1>:
hvori A betegner 1,4-fenylen eller trans-1,4-cyclohexylen, og n er 0 eller 1.
Fremstilling av fasene ifølge oppfinnelsen skjer på i og for seg kjent måte. Generelt oppløses komponentene i hverandre, hensiktsmessig ved forhøyet temperatur.
Gjennom egnede tilsetninger kan de flytende-krystallinske faser ifølge oppfinnelsen modifiseres slik at de kan anvendes i alle tidligere kjente, foreliggende typer av flytende-krystallinske tegnelementer.
De etterfølgende eksempler illustrerer oppfinnelsen uten å begrense denne. I det foregående og det etterfølgende betegner prosentangivelser vektprosent; alle temperaturer er angitt i grader Celsius. Enn videre betyr: K: krystallin-fast tilstand, S: smektisk fase (indekset kjennetegner fase-typen), N: nematisk tilstand, Ch: cholestrisk fase, I: iso-trop fase. Tallene mellom to symboler angir omvandlingstemp-eraturen i grader Celsius. "Vanlig opparbeidelse" betyr: vann tilsettes, det ekstraheres med methylenklorid, separeres, den organiske fase tørkes, inndampes, og produktet renses ved krystallisasjon og/eller kromatografi.
Eksempel 1
Til 10,1 g diisopropylamin i 70 m THF ble under fuktighetsutelukkelse og nitrogenatmosfære ved -10°C suksessivt dråpevis tilsatt 62,5 ml av en 1,6 m løsning av N-butyllithium i hexan og 36,1 g trans-4-[5-(p-n-heptylfenyl)-2-pyrimidinyl]-cyclohexancarbonitril (EP-OS 00 14 885) i 50 ml THF. Reaksjonsblandingen ble deretter omrørt ved -10°C i 20 minutter.
16,6 g 1-brompentan ble deretter tilsatt, og reaksjonsblandingen ble omrørt i 20 minutter ved romtemperatur. Reaksjonsblandingen ble opparbeidet på vanlig måte, og produktet ble renset ved kromatografi og krystallisasjon. Det ble erholdt r-l-cyan-l-n-pentyl-cis-4-[5-(p-n-heptylfenyl)-2-pyrimidinyl]-cyclohexan.
Analogt ble fremstilt: r-1-cyan-1-propyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-l-butyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-hexyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-l-octyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-l-nonyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-decyl-cis-4-[5-(p-heptylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-propyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-butyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-pentyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-hexyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-heptyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-l-nonyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-1-decyl-cis-4-[5-(p-octylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-propyl-cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-butyl-cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-hexyl-cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-heptyl-cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-nonyl-cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-decyl—cis-4-[5-(p-nonylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-propyl-cis-4-[5-(p-decylfeny1)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-butyl-cis-4-[5-(p-decylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-hexyl-cis-4-[5-(p-decylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-1-heptyl-cis-4-[5-(p-decylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[5-(p-decylfenyl)-2-pyrimidinyl]-cyclohexan
r-l-cyan-l-nonyl-cis-4-[5-(p-decylfenyl)-2-pyrimidinyl]-cyclohexan
r-1-cyan-l-decyl-cis-4-[5-(p-decylfenyl)-2-pyrimidinyl]-cyclohexan
Eksempel 2
Til en løsning av 4,6 g natrium i 150 ml methanol ble tilsatt 34,7 g p-(4-n-hexyl-4-cyanocyclohexyl)-benzamidin-hydroklorid og 20,4 g 2-n-pentyl-3-ethoxyacrolein (analogt med A. Villiger, A. Boller, M. Schadt, Z. Naturforsch. 34b, 1535, 1979), reaksjonsblandingen ble omrørt i 12 timer under nitrogenatmosfære, ble surgjort med 3N HC1 og ble opparbeidet på vanlig måte. Det ble erholdt r-l-cyan-l-hexyl-cis-4-[p-(5-n-pentylpyrimidinyl-2)-fenyl]-cyclohexan.
Analogt ble fremstilt: r-l-cyan-l-hexyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan, r-l-cyan-l-hexyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan, r-l-cyan-l-hexyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan, r-l-cyan-l-hexyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan, r-l-cyan-l-hexyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-pentyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-pentyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-decylpyrimidinyl-2)-feny1]-cyclohexan,
r-1-cyan-1-heptyl-cis-4-[p-(5-propylpyrimidinyl-2)-fenyl]-cyclohexan, smp. 94°, kp. 143°,
r-l-cyan-l-heptyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-heptyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan, smp. 101°, kp. 126°,
r-l-cyan-l-heptyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-octyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-octyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-decyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-1-cyan-1-decyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-decyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-decyl-cis-4-[p-(5-heptylpyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-decyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-decyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-decyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-penty l-cis-4- [ p- (5-butylpyrimidinyl-2) -f enyl ] - cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p- (5-pentylpyrimidinyl-2) -fenyl] - cyclohexan,
r-l-cyan-l-penty l-cis-4-[p- (5-hexylpyrimidinyl-2) -f enyl] - cyclohexan,
r-l-cyan-1- penty l-cis-4- [ p- (5-hepty lpyrimidinyl-2) -f enyl ] - cyclohexan,
r-1-cyan-1-penty 1-cis-4-[p- (5-oc ty lpyrimidinyl-2) - f enyl ] - cyclohexan,
r-1-cyan-1-penty l-cis-4-[p- (5-nony lpyrimidinyl-2) - f enyl ] - cyclohexan,
r-1-cyan-1-penty l-cis-4-[ p- (5-decy lpyrimidinyl-2) - f enyl ] - cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-nonylpyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-butylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-pentylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-hexylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-nonylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-decylpyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidiny1-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl) - pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-decylcyclohexy1)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-.pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-butyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-pentyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-hexyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-hexylcyclohexy1)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-heptyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-heptylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-octyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-butylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-pentylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-hexylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-heptylcyclohexy1)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-octylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-nonylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan,
r-l-cyan-l-nonyl-cis-4-[p-(5-(trans-4-decylcyclohexyl)-pyrimidinyl-2)-fenyl]-cyclohexan.
Eksempel 3
Det ble fremstilt en flytende-krystallinsk fase bestående av
4% 2-p-heptyloxyfenyl-5-heptylpyrimidin,
30% 2-p-undecyloxyfenyl-5-hexylpyrimidin,
30% 2-p-nonyloxyfenyl-5-nonylpyrimidin,
12% r-l-cyan-cis-4-[p-(5-heptylpyrimidinyl-2)-fenyl]-cyclo-hexan- 1-carboxyl sy repen ty lester ,
14% r-l-cyan-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclo-hexan-l-carboxylsyrebutylester og
10% p-(5-hexylpyrimidinyl-2)-fenyl-2-klorpropionat (optisk
aktiv).
Eksempel 4
Det ble fremstilt en flytende-krystallinsk fase bestående av
20% 4-(5-hexylpyrimidin-2-y1)-fenyl-(p-pentylbenzyl)-ether, 20% 4-(5-heptylpyrimidin-2-yl)-fenyl-(p-hexylbenzyl)-ether, 20% 4-(5-nonylpyrimidin-2-yl)-fenyl-(p-propylbenzy1)-ether,
5% 4-(5-nonylpyrimidin-2-yl)-fenyl-(p-cyanbenzyl)-ether,
10% r-l-cyan-cis-4-[p-(5-heptylpyrimidiny1-2)-fenyl]-cyclohexan-l-carboxylsyrebutylester,
15% r-l-cyan-cis-4-[p-(5-octylpyrimidinyl-2)-fenyl]-cyclo-hexan- 1-carboxyl sy repenty le ster og
10% p-(5-hexylpyrimidinyl-2)-fenyl-2-klorpropionat (optisk
aktiv).
Eksempel 5
En flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfenyl-5-heptylpyrimidin,
3% 2-p-heptyloxyfeny1-5-heptylpyrimidin,
3% 2-p-octyloxyfenyl-5-heptylpyrimidin,
3% 2-p-nonyloxyfeny1-5-heptylpyrimidin,
8% 2-p-hexyloxyfenyl-5-nonylpyrimidin,
25% 2-p-nonyloxyfenyl-5-nonylpyrimidin,
30% r-l-cyan-cis-4-(4<1->octyloxybifenyl-4-yl)-1-octyl-cyclohexan,
15% r-l-cyan-cis-4-(4<1->nonanoyloxybifenyl-4-yl)-1-butyl-cyclohexan og
10% r-l-cyan-cis-4-[p-(5-nonylpyrimidin-2-yl)-fenyl]-l-(2-methylbutyl)-cyclohexan (optisk aktiv)
har K -8° S<*>65° og sj og P = 8 nC/cm<2>ved 20°.
Eksempel 6
Det ble fremstilt en flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfeny1-5-heptylpyrimidin,
3% 2-p-heptyloxyfenyl-5-heptylpyrimidin,
3% 2-p-octyloxyfeny1-5-heptylpyrimidin,
3% 2-p-nonyloxyfeny1-5-heptylpyrimidin,
8% 2-p-hexyloxyfenyl-5-nonylpyrimidin,
25% 2-p-nonyloxyfenyl-5-nonylpyrimidin,
20% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-octyloxyfenyl)-cyclohexan,
10% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-heptyloxyfenyl)-cyclohexan,
10% r-l-cyan-1-(trans-4-octylcyclohexy1-ethyl)-cis-4-(p-octylfenyl)-cyclohexan,
5% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-heptylfenyl)-cyclohexan,
10% r-l-cyan-cis-4-[p-(5-octylpyrimidin-2-yl)-fenyl]-l-(2-methylbutyl)-cyclohexan (optisk aktiv).
Eksempel 7
En flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfeny1-5-heptylpyrimidin,
3% 2-p-heptyloxyfeny1-5-heptylpyrimidin,
3% 2-p-octyloxyfeny1-5-heptylpyrimidin,
3% 2-p-heptyloxyfeny1-5-heptylpyrimidin,
3% 2-p-octyloxyfenyl-5-heptylpyrimidin,
3% 2-p-nonyloxyfenyl-5-heptylpyrimidin,
8% 2-p-hexyloxyfeny1-5-nonylpyrimidin,
2 5% 2-p-nonyloxyfeny1-5-nonylpyrimidin,
30% r-l-cyan-cis-4-(4<1->octyloxybifenyl-4-yl)-1-octyl-cyclohexan,
15% r-l-cyan-cis-4-(4'-nonanoyloxybifenyl-4-yl)-1-buty1-cyclohexan og
10% r-l-cyan-cis-4-[p-(5-nonylpyrimidin-2-yl)-fenyl]-1-(2-methylbutyl)-cyclohexan (optisk aktiv)
har K -8° S<*>65° og S<*>og P = 8 nC/cm<2>ved 20°.
Eksempel 6
Det ble fremstilt en flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfeny1-5-heptylpyrimidin,
3% 2-p-heptyloxyfenyl-5-heptylpyrimidin,
3% 2-p-octyloxyfenyl-5-heptylpyrimidin,
3% 2-p-nonyloxyfenyl-5-heptylpyrimidin,
8% 2-p-hexyloxyfeny1-5-nonylpyrimidin,
25% 2-p-nonyloxyfeny1-5-nonylpyrimidin,
20% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-octyloxyfenyl)-cyclohexan,
10% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-heptyloxyfenyl)-cyclohexan,
10% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-octylfenyl)-cyclohexan,
5% r-l-cyan-1-(trans-4-octylcyclohexyl-ethyl)-cis-4-(p-heptylfenyl)-cyclohexan,
10% r-l-cyan-cis-4-[p-(5-octylpyrimidin-2-yl)-fenyl]-l-(2-methylbutyl)-cyclohexan (optisk aktiv).
Eksempel 7
En flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfeny1-5-heptylpyrimidin,
3% 2-p-heptyloxyfeny1-5-heptylpyrimidin,
3% 2-p-octyloxyfeny1-5-heptylpyrimidin,
3% 2-p-nonyloxyfeny1-5-heptylpyrimidin,
8% 2-p-hexyloxyfenyl-5-nonylpyrimidin,
25% 2-p-nonyloxyfeny1-5-nonylpyrimidin,
30% r-l-cyan-cis-4-[p-(p-octyloxybenzoyloxy)-fenyl]-1-octyl-cyclohexan,
15% r-l-cyan-cis-4-[p-(p-octyloxybenzoyloxy)-fenyl]-1-penty1-cyclohexan,
10% r-l-cyan-cis-4-[p-(5-nonyloxypyrimidin-2-yl)-fenyl]-l-(2-methylbutyl)-cyclohexan (optisk aktiv)
har K -10° S<*>61° S<*>og P = 10 nC/cm<2>ved 20°.
Eksempel 8
Det ble fremstilt en flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfeny1-5-heptylpyrimidin,
3% 2-p-heptyloxyfeny1-5-heptylpyrimidin,
3% 2-p-octyloxyfenyl-5-heptylpyrimidin,
3% 2-p-nonyloxyfeny1-5-heptylpyrimidin,
8% 2-p-hexyloxy f eny.l-5-nony lpyrimidin,
25% 2-p-nonyloxyfeny1-5-nonylpyrimidin,
15% l-cyan-l-trans-4-(p-heptyloxyfenyl)-cyclohexyl-2-(trans-4-octylcyclohexyl)-ethan,
15% l-cyan-l-trans-4-(p-octyloxyfenyl)-cyclohexyl-2-(trans-4-octylcyclohexyl)-ethan,
10% l-cyan-l-trans-4-(p-octylfenyl)-cyclohexyl-2-(trans-4-butylcyclohexyl)-ethan,
5% l-cyan-l-trans-4-(p-heptylfenyl)-cyclohexyl-2-(trans-4-butylcyclohexy1)-ethan og
10% r-l-cyan-cis-4-[p-(5-octylpyrimidin-2-yl)-fenyl]-1-(2-methylbutyl)-cyclohexan.
Eksempel 9
Det ble fremstilt en flytende-krystallinsk fase bestående av
3% 2-p-hexyloxyfenyl-5-heptylpyrimidin,
3% 2-p-heptyloxyfeny1-5-heptylpyrimidin,
3% 2-p-octyloxyfenyl-5-heptylpyrimidin,
3% 2-p-nonyloxyfenyl-5-heptylpyrimidin,
8% 2-p-hexyloxyfeny1-5-nonylpyrimidin,
25% 2-p-nonyloxyfeny1-5-nonylpyrimidin,
10% r-l-cyan-cis-4-(p-octyloxyfenyl)-1-octylcyclohexan,
10% r-l-cyan-cis-4-(4<1->octyloxycarbonylbifenyl-4-yl)-1-octyl-cyclohexan ,
5% r-l-cyan-cis-4-(p-heptyloxybenzoyloxy)-1-nonylcyclohexan, 10% r-l-cyan-cis-4-[p-(p-octylfenyl)-benzoyloxy]-1-butyl-cyclohexan,
5% r-l-cyan-cis-4-[p-(p-octyloxyfenyl)-benzoyloxy]-1-butyl-cyclohexan og
15% r-l-cyan-cis-4-[p-(5-nonylpyrimidin-2-yl)-fenoxycarbonyl]-1-(2-methylbutyl)-cyclohexan (optisk aktiv).
Eksempel 10
Til en blanding av 3,2 g 2-p-hydroxyfenyl-5-hexyl-pyrimidin, 3,15 g 4-cyan-4-heptylcyclohexancarboxylsyre (som kan erholdes fra 4-cyancyclohexancarboxylsyre ved omsetning med n-heptylbromid i nærvær av 2 ekvivalenter lithiumdiisopropylamid) og 150 mg 4-N,N'-dimethylaminopyridin i 150 ml diklormethan ble ved 5 - 10° og under fuktighetsutelukkelse tilsatt 2,8 g dicyclohexylcarbodiimid i 50 ml methylenklorid, blandingen ble omrørt en time ved romtemperatur, det utfelte ureaderivat ble fjernet, og filtratet ble opparbeidet på vanlig måte. Det ble erholdt r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-hexylpyrimidin-2-yl)-fenylester.
Analogt ble fremstilt: r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-propylpyrimidin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-butylpyrimidin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-pentylpyrimidin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-heptylpyrimidin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-octylpyrimidin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-nonylpyrimidin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-decylpyrimidin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-propylpyrimidin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-butylpyrimidin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-pentylpyrimidin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-hexylpyrimidin-2-yl)-fenylester
r-1-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-heptylpyrimidin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-octylpyrimidin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-nonylpyrimidin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-decylpyrimidin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-propylpyrimidin-2-y1)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-butylpyrimidin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-pentylpyrimidin-2-y1)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-hexylpyrimidin-2-yl)-fenylester
r-1-cyan-1-nonylcyclohexan-cis-4-carboxylsyre-p-(5-heptylpyrimidin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-octylpyrimidin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-nonylpyrimidin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-decylpyrimidin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-propylpyridin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-butylpyridin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-pentylpyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-hexylpyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-heptylpyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-octylpyridin-2-yl)-fenylester
r-1-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-nonylpyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-decylpyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-butoxypyridin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-pentoxypyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-hexoxypyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-heptoxypyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-octoxypyridin-2-yl)-fenylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-p-(5-nonoxypyridin-2-yl)-fenylester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-p-(5-decoxypyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-propylpyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-butylpyridin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-cis-4-carboxy1syre-p-(5-pentylpyridin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-cis-4-carboxy1syre-p-(5-hexylpyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-heptylpyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxy1syre-p-(5-octylpyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxy1syre-p-(5-nonylpyridin-2-yl)-fenylester
r-1-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-decylpyridin-2-yl)-fenylester
r-1-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-butoxypyridin-2-yl)-fenylester r-l-cyan-l-octylcyclohexan-cis-4-carboxy1syre-p-(5-pentoxypyridin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-hexoxypyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-heptoxypyridin-2-yl)-fenylester
r-1-cyan-1-octylcyclohexan-cis-4-carboxylsyre-p-(5-octoxypyridin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-cis-4-carboxylsyre-p-(5-nonoxypyridin-2-yl)-fenylester
r-l-cyan-l-octylcyclohexan-ci,s-4-carboxylsyre-p- (5-decoxypyridin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-propylpyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p- (5-butylpyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-pentylpyridin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-hexylpyridin-2-yl)-fenylester
r-1-cyån-1-nonylcyclohexan-cis-4-carboxylsyre-p-(5-heptylpyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-octylpyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-nonylpyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-decylpyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-butoxypyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-pentoxypyridin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-hexoxypyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-heptoxypyridin-2-yl)-fenylester
r-1-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-octoxypyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-nonoxypyridin-2-yl)-fenylester
r-l-cyan-l-nonylcyclohexan-cis-4-carboxylsyre-p-(5-decoxypyridin-2-yl)-fenylester
r-l-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-propylpyrimidin-2-yl)-fenylester
r-l-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-butylpyrimidin-2-yl)-fenylester
r-l-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-pentylpyrimidin-2-y1)-fenylester
r-l-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-hexylpyrimidin-2-yl)-fenylester
r-l-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-heptylpyrimidin-2-yl)-fenylester
r-l-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-octylpyrimidin-2-yl)-fenylester
r-1-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-nonylpyrimidin-2-yl)-fenylester
r-1-cyan-cis-4-heptylcyclohexancarboxylsyre-p-(5-decylpyrimidin-2-yl)-fenylester
5-propyl-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-butyl-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-pentyl-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-hexyl-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-hepty1-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-octy1-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-nony1-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-decy1-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-butoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-pentoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-hexoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-heptoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-octoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-nonoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
5-decoxy-pyridin-2-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-propy1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-buty1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-penty1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-hexy1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-hepty1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-octy1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-nonyl-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-decy1-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-butoxy-pyridin-5-carboxylsyre-(4-cyan-4-heptyl-cyclohexylester
2-pentoxy-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-hexoxy-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-heptoxy-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-octoxy-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-nonoxy-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
2-decoxy-pyridin-5-carboxylsyre-(4-cyan-4-hepty1-cyclohexylester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-propylpyridin-5-yl-ester
r-l-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-butylpyridin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-(2-pentylpyridin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-(2-hexylpyridin-5— yl-ester
r-l-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-heptylpyridin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-octylpyridin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-nonylpyridin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-decylpyridin-5-yl-ester
r-l-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-butoxypyridin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-(2-pentoxypyridin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-(2-hexoxypyridin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-(2-heptoxypyridin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-(2-octoxypyridin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-(2-nonoxypyridin-5-yl-ester
r-1-cyan-1-hepty lcyclohexan-cis-4-carboxy lsyre-.( 2-decoxypyridin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-propylfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-buty1fenyl)-pyridazin-3-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-pentylfenyl)-pyridazin-3-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-hexylfenyl)-pyridazin-3-yl-ester
r-1-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-heptylfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-octylfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-nonylfenyl)-pyridazin-3-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-decylfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-butoxyfenyl)-pyridazin-3-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-pentoxyfenyl)-pyridazin-3-yl-ester
r-l-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-hexoxyfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-heptoxyfenyl)-pyridazin-3-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-octoxyfenyl)-pyridazin-3-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-6-(p-nonoxyfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-6-(p-decoxyfenyl)-pyridazin-3-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-5-(p-propylfenyl)-pyrazin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-butylfenyl)-pyrazin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-pentylfenyl)-pyrazin-5-yl-ester
r-l-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-octylfenyl)-pyrazin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-nonylfenyl)-pyrazin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-5-(p-decylfenyl)-pyrazin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-butoxyfenyl)-pyrazin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-5-(p-pentoxyfenyl)-pyrazin-5-yl-ester
r-l-cyan-l-heptylcyclohexan-cis-4-carboxylsyre-5-(p-hexoxyfenyl)-pyrazin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-heptoxyfenyl)-pyrazin-5-yl-ester
r-l-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-octoxyfenyl)-pyrazin-5-y1-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-nonoxyfenyl)-pyrazin-5-yl-ester
r-1-cyan-1-heptylcyclohexan-cis-4-carboxylsyre-5-(p-decoxyfenyl)-pyrazin-5-yl-ester
p-(5-propylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-butylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-pentylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-hexylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-heptylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-octylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-nonylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-decylpyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-butoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-pentoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-hexoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-heptoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-octoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-nonoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-decoxypyrimidin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-propylpyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-butylpyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-pentylpyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-hexylpyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-heptylpyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-octylpyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-nonylpyridin-2-y1)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-decylpyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-butoxypyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-pentoxypyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-hexoxypyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-heptoxypyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-octoxypyridin-2-yl)-benzosyre-(4-cyan-4-heptyl-cyclohexyl)-ester
p-(5-nonoxypyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
p-(5-decoxypyridin-2-yl)-benzosyre-(4-cyan-4-hepty1-cyclohexyl)-ester
Eksempel 11
En blanding av 61,2 g 2-p-hydroxyfeny1-5-heptyl-pyridin (som kan erholdes fra 2-p-methoxyfeny1-5-heptyl-pyridin ved basisk etherspaltning med kalium-tert.-butylat i N-methylpyrrolidon ved 150°), 35 g kaliumcarbonat og 85 g 4-cyan-4-heptylcyclohexylmethyljodid (som kan erholdes ved red-uksjon av 4-cyan-4-heptylcyclohexancarboxylsyreethylester med LiBH^, overføring av carbinolen i mesylat og omsetning med NaJ/aceton etter Finkelstein) i 500 ml dimethylformamid ble omrørt under nitrogenatmosfære ved 110° i 8 timer. Etter vanlig opparbeidelse ble det erholdt r-l-cyan-l-heptyl-cis-4-[p-(5-heptylpyridin-2-yl)-fenoxy-methyl]-cyclohexan.
Analogt ble fremstilt: r-l-cyan-l-octyl-cis-4-[p-(5-propylpyridin-2-y1)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-butylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-pentylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-hexylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-heptylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-octylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-nonylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-decylpyridin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-propylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-butylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-pentylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-hexylpyrimidin-2-y1)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-heptylpyrimidin-2-y1)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-octylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-nonylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-heptyl-cis-4-[p-(5-decylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-propylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-butylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-pentylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-hexylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-heptylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-octylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-nonylpyrimidin-2-yl)-fenoxymethyl]-cyclohexan
r-l-cyan-l-octyl-cis-4-[p-(5-decylpyrimidin-2-yl) - fenoxymethyl]-cyclohexan
Claims (5)
1. Nitrogenholdige, heterocykliske forbindelser av formel II
hvori
1 2
R og R betegner en alkylgruppe med 1 til 15 C-atomer,
hvori også én eller flere CF^-grupper kan være erstattet med en gruppering valgt fra gruppen -0-, -S-, -CO-, -0-CO-,
-0-COO-, -CO-0-, -CH=CH -, -CH-halogen og -CHCN-, eller også av en kombinasjon av to egnede grupperinger, hvorved to heteroatomer ikke kan være direkte forbundet med hverandre,
m er 0 eller 1,
Ar betegner 1,4-fenylen, 4,4 <1-> bifenylyl eller 2,6-nafthylen, hvorved én eller flere CH-grupper kan være erstattet med N,
Z betegner -CO-0-, -0-CO-, -CH2 0-, -0CH2 -, -CH2 CH2" ,
-CH2 CHCN-, -CHCNCH2 -, -CH=CH eller en enkeltbinding, og A betegner usubstituert eller i 1- eller 4-stilling CN-substituert 1,4-cyclohexylen,
med det forbehold at i det tilfelle A = usubstituert 1,4-cyclohexylen, betegner Z -CHCNCH-- eller -CH„CHCN, og/eller 12.^
at i minst en av restene R og R er minst en CH2~ gruppe erstattet med -CHCN-.
2. Anvendelse av forbindelsene av formel II ifølge krav 1 som komponenter av smektiske, flytende-krystallinske faser.
3. Smektisk, flytende-krystallinsk fase med minst to flytende-krystallinske komponenter, karakterisert ved at den minst inneholder en forbindelse av formel II ifølge krav 1.
4. Fase ifølge krav 3,
karakterisert ved at den inneholder minst én optisk aktiv forbindelse.
5. Elektrooptisk tegnelement, karakterisert ved at det som dielektrikum inneholder en fase ifølge krav 3 eller 4.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19853533333 DE3533333A1 (de) | 1985-09-18 | 1985-09-18 | Smektische fluessigkristalline phasen |
PCT/EP1986/000530 WO1987001701A2 (fr) | 1985-09-18 | 1986-09-15 | Composes heterocycliques contenant de l'azote |
Publications (2)
Publication Number | Publication Date |
---|---|
NO872039L true NO872039L (no) | 1987-05-15 |
NO872039D0 NO872039D0 (no) | 1987-05-15 |
Family
ID=6281320
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO872039A NO872039D0 (no) | 1985-09-18 | 1987-05-15 | Nitrogenholdige heterocykliske forbindelser. |
Country Status (8)
Country | Link |
---|---|
US (1) | US5002694A (no) |
EP (1) | EP0238576B1 (no) |
JP (2) | JPS63500945A (no) |
KR (1) | KR870700610A (no) |
DD (2) | DD252197A5 (no) |
DE (2) | DE3533333A1 (no) |
NO (1) | NO872039D0 (no) |
WO (1) | WO1987001701A2 (no) |
Families Citing this family (22)
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---|---|---|---|---|
US5180521A (en) * | 1986-02-17 | 1993-01-19 | Merck Patent Gesellschaft Mit Beschraenkter Haftung | Chiral compounds |
JPS63502507A (ja) * | 1986-02-17 | 1988-09-22 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 光学活性化合物 |
DE3614778A1 (de) * | 1986-05-02 | 1987-11-05 | Merck Patent Gmbh | Smektische fluessigkristalline phasen |
DE3621581A1 (de) * | 1986-06-27 | 1988-01-07 | Merck Patent Gmbh | Polymerisierbare fluessigkristallmaterialien |
JPH01500860A (ja) * | 1986-09-16 | 1989-03-23 | メルク・パテント・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | Ecb効果にもとづく電気光学表示素子用の液晶相 |
DE3787253D1 (de) * | 1986-11-20 | 1993-10-07 | Hoffmann La Roche | Ferroelektrische Flüssigkristalle. |
US5232625A (en) * | 1986-12-08 | 1993-08-03 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Cyano-alicyclic esters in liquid crystal compositions |
GB8629322D0 (en) * | 1986-12-08 | 1987-01-14 | Secr Defence | Cyano-terpenoid esters |
DE3852422T2 (de) * | 1987-04-27 | 1995-05-04 | Chisso Corp | Optisch aktive 2-Biphenylpyrimidinderivate und diese enthaltende Flüssigkristallmischungen. |
GB8712464D0 (en) * | 1987-05-27 | 1987-07-01 | Merck Patent Gmbh | Liquid crystal phase |
DE3731639A1 (de) * | 1987-09-19 | 1989-03-30 | Hoechst Ag | Fluessigkristalline phenylpyrimidin-cyclohexancarbonsaeureester, verfahren zu ihrer herstellung und ihre verwendung in fluessigkristallmischungen |
GB8724458D0 (en) * | 1987-10-19 | 1987-11-25 | Secr Defence | Lateral cyano terphenyls |
CA1336441C (en) * | 1987-12-28 | 1995-07-25 | Manabu Uchida | Liquid crystal composition |
JPH0312484A (ja) * | 1989-06-09 | 1991-01-21 | Canon Inc | 強誘電性カイラルスメクチック液晶組成物おこよびこれを含む液晶素子 |
JPH0312480A (ja) * | 1989-06-09 | 1991-01-21 | Canon Inc | 強誘電性カイラルスメクチック液晶組成物およびこれを含む液晶素子 |
JPH0312477A (ja) * | 1989-06-09 | 1991-01-21 | Canon Inc | 強誘電性カイラルスメクチック液晶組成物およびこれを含む液晶素子 |
JP2763339B2 (ja) * | 1989-07-31 | 1998-06-11 | キヤノン株式会社 | 液晶組成物およびこれを使用した液晶素子 |
GB9002830D0 (en) * | 1990-02-08 | 1990-04-04 | Secr Defence | L.c.cyanoalkenes & alkenes |
JP2796753B2 (ja) * | 1990-05-09 | 1998-09-10 | キヤノン株式会社 | カイラルスメクチック液晶組成物およびそれを使用した液晶素子 |
US5128061A (en) * | 1990-08-14 | 1992-07-07 | Optical Shields, Inc. | Phenyl-pyrimidine liquid crystal materials |
JP3015998B2 (ja) * | 1993-08-31 | 2000-03-06 | キヤノン株式会社 | 液晶性化合物、それを含む液晶組成物、該液晶組成物を用いた液晶素子、液晶装置、並びに表示方法 |
US6824707B2 (en) * | 2001-10-23 | 2004-11-30 | Clariant International Ltd. | Active matrix liquid crystal device and smectic liquid crystal mixture |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS5939876A (ja) * | 1982-08-26 | 1984-03-05 | Chisso Corp | ピリミジン誘導体 |
DE3382646D1 (de) * | 1982-08-26 | 1993-01-28 | Merck Patent Gmbh | Cyclohexanderivate und ihre verwendung als komponenten fluessigkristalliner-dielektrika. |
EP0111695A3 (de) * | 1982-11-19 | 1985-08-21 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyridazinderivate |
EP0110299B2 (en) * | 1982-11-26 | 1993-06-09 | Hitachi, Ltd. | Smectic liquid crystal compounds and liquid crystal compositions |
DE3325727A1 (de) * | 1983-07-16 | 1985-01-24 | Merck Patent Gmbh, 6100 Darmstadt | Fluessigkristalline verbindungen |
DE3332692A1 (de) * | 1983-09-10 | 1985-03-28 | Merck Patent Gmbh, 6100 Darmstadt | Anisotrope verbindungen und fluessigkristallmischungen |
DE3332691A1 (de) * | 1983-09-10 | 1985-03-28 | Merck Patent Gmbh, 6100 Darmstadt | Anisotrope verbindungen und fluessigkristallmischungen |
GB8400665D0 (en) * | 1984-01-11 | 1984-02-15 | Secr Defence | Disubstituted ethanes |
DE3404116A1 (de) * | 1984-02-07 | 1985-08-08 | Merck Patent Gmbh, 6100 Darmstadt | Stickstoffhaltige heterocyclen |
DE3566901D1 (en) * | 1984-04-07 | 1989-01-26 | Merck Patent Gmbh | Liquid crystal phase |
EP0191860B1 (en) * | 1984-06-07 | 1990-04-18 | Seiko Instruments Inc. | Liquid crystal compound |
DE3566113D1 (en) * | 1984-06-29 | 1988-12-15 | Hoffmann La Roche | Cyclohexanecarbonitriles and their use as components for liquid crystals |
GB8428653D0 (en) * | 1984-11-13 | 1984-12-19 | Secr Defence | Diesters |
DE3500909A1 (de) * | 1985-01-12 | 1986-07-17 | Merck Patent Gmbh, 6100 Darmstadt | Pyrimidine |
DE3506446A1 (de) * | 1985-02-23 | 1986-08-28 | Merck Patent Gmbh, 6100 Darmstadt | Pyrimidinderivate |
DE3510434A1 (de) * | 1985-03-22 | 1986-09-25 | Merck Patent Gmbh, 6100 Darmstadt | Cyclohexanderivate |
DE3515373A1 (de) * | 1985-04-27 | 1986-11-06 | Merck Patent Gmbh, 6100 Darmstadt | Stickstoffhaltige heterocyclen |
DE3515374C2 (de) * | 1985-04-27 | 1998-02-26 | Hoechst Ag | Chirale getilte smektische flüssigkristalline Phasen und deren Verwendung in elektrooptischen Anzeigeelementen |
DE3518734A1 (de) * | 1985-05-24 | 1986-11-27 | Merck Patent Gmbh, 6100 Darmstadt | Smektische fluessigkristalline phasen |
DD240385A1 (de) * | 1985-08-26 | 1986-10-29 | Univ Halle Wittenberg | Anwendung ferroelektrischer fluessigkristalle |
DE3600052A1 (de) * | 1986-01-03 | 1987-07-09 | Merck Patent Gmbh | Heterocyclische verbindungen |
EP0263843B1 (en) * | 1986-02-21 | 1992-12-02 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern | Liquid crystal compounds, mixtures and devices |
DE3706766A1 (de) * | 1986-03-14 | 1987-09-17 | Merck Patent Gmbh | Smektische fluessigkristalline phasen |
DE3788243D1 (de) * | 1986-05-22 | 1994-01-05 | Hoffmann La Roche | Flüssigkristalline Derivate von Phenylbenzoat. |
DE3765842D1 (de) * | 1986-05-30 | 1990-12-06 | Hoechst Ag | Chirale ester aus alpha-substituierten carbonsaeuren und mesogenen pyrimidin-5-yl-phenolen und ihre verwendung als dotierstoff in fluessigkristall-phasen. |
US4777280A (en) * | 1986-07-01 | 1988-10-11 | University Patents, Inc. | Phenylbenzoate 1-cyanoalkoxy compounds |
-
1985
- 1985-09-18 DE DE19853533333 patent/DE3533333A1/de not_active Withdrawn
-
1986
- 1986-09-15 JP JP61505361A patent/JPS63500945A/ja active Pending
- 1986-09-15 US US07/071,226 patent/US5002694A/en not_active Expired - Lifetime
- 1986-09-15 WO PCT/EP1986/000530 patent/WO1987001701A2/de active IP Right Grant
- 1986-09-15 DE DE8686905780T patent/DE3685213D1/de not_active Expired - Fee Related
- 1986-09-15 EP EP86905780A patent/EP0238576B1/de not_active Expired - Lifetime
- 1986-09-15 JP JP61504895A patent/JP2777885B2/ja not_active Expired - Fee Related
- 1986-09-18 DD DD86294527A patent/DD252197A5/de not_active IP Right Cessation
- 1986-09-18 DD DD86294525A patent/DD252196A5/de unknown
-
1987
- 1987-05-15 NO NO872039A patent/NO872039D0/no unknown
- 1987-05-15 KR KR870700426A patent/KR870700610A/ko not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
DE3533333A1 (de) | 1987-03-26 |
WO1987001701A3 (fr) | 1987-06-18 |
JP2777885B2 (ja) | 1998-07-23 |
WO1987001701A2 (fr) | 1987-03-26 |
JPS63500945A (ja) | 1988-04-07 |
EP0238576B1 (de) | 1992-05-06 |
JPS63500948A (ja) | 1988-04-07 |
US5002694A (en) | 1991-03-26 |
EP0238576A1 (de) | 1987-09-30 |
KR870700610A (ko) | 1987-12-30 |
DD252197A5 (de) | 1987-12-09 |
NO872039D0 (no) | 1987-05-15 |
DD252196A5 (de) | 1987-12-09 |
DE3685213D1 (de) | 1992-06-11 |
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