JP5531475B2 - 重合性キラル化合物 - Google Patents
重合性キラル化合物 Download PDFInfo
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- JP5531475B2 JP5531475B2 JP2009164596A JP2009164596A JP5531475B2 JP 5531475 B2 JP5531475 B2 JP 5531475B2 JP 2009164596 A JP2009164596 A JP 2009164596A JP 2009164596 A JP2009164596 A JP 2009164596A JP 5531475 B2 JP5531475 B2 JP 5531475B2
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- 150000001875 compounds Chemical class 0.000 title claims description 131
- 239000000203 mixture Substances 0.000 claims description 71
- 239000004973 liquid crystal related substance Substances 0.000 claims description 70
- -1 naphthalene-2,6-diyl group Chemical group 0.000 claims description 38
- 230000003287 optical effect Effects 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 88
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
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- 239000000243 solution Substances 0.000 description 26
- 0 Oc1ccc(*[C@]2[C@@]3OC[C@](*c(cc4)ccc4O)[C@]3OC2)cc1 Chemical compound Oc1ccc(*[C@]2[C@@]3OC[C@](*c(cc4)ccc4O)[C@]3OC2)cc1 0.000 description 24
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 239000000758 substrate Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 16
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
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- 238000004519 manufacturing process Methods 0.000 description 14
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- 239000010409 thin film Substances 0.000 description 12
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
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- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 7
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- 239000000706 filtrate Substances 0.000 description 6
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 6
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- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 6
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
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- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 4
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 125000006850 spacer group Chemical group 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 125000005843 halogen group Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- KLDXJTOLSGUMSJ-KVTDHHQDSA-N (3r,3ar,6r,6ar)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@@H]1CO[C@@H]2[C@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-KVTDHHQDSA-N 0.000 description 2
- 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 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 2
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- 239000002585 base Substances 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- SXGBREZGMJVYRL-UHFFFAOYSA-N butan-1-amine;hydrobromide Chemical compound [Br-].CCCC[NH3+] SXGBREZGMJVYRL-UHFFFAOYSA-N 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
- 229910052918 calcium silicate Inorganic materials 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 230000002999 depolarising effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
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- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007765 extrusion coating Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical class COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000002832 nitroso derivatives Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 238000011907 photodimerization Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003232 pyrogallols Chemical class 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- GRGCWBWNLSTIEN-UHFFFAOYSA-N trifluoromethanesulfonyl chloride Chemical compound FC(F)(F)S(Cl)(=O)=O GRGCWBWNLSTIEN-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Liquid Crystal Substances (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明の化合物は以下に記載する合成方法で合成することができる。
(製法1) 一般式(I-1)で表される化合物の製造
p-ブロモ安息香酸とイソソルビドをジシクロヘキシルカルボジイミド等の脱水縮合剤を用いてエステル化反応させ、更に生成物とヒドロキシエチルアクリレートとをパラジウム触媒を用いたヘック反応により、イソソルビド誘導体(S-2)を得る。
6-ヒドロキシ-2-ナフトエ酸とトリフルオロメタンスルホニルクロリドとを反応させた後、更にイソソルビドをジシクロヘキシルカルボジイミド等の脱水縮合剤を用いてエステル化反応させイソソルビド誘導体(S-3)を得る。
p-ヒドロキシ安息香酸とベンジルクロリドとを水酸化ナトリウムなど適当な塩基の存在下でエーテル化反応させてフェノールに保護基を結合させた後、ジシクロヘキシルカルボジイミド等の脱水縮合剤を用いてエステル化応させ、更に生成物をパラジウム触媒を用いた水素添加による還元反応によりフェノール保護基を脱離させイソソルビド誘導体(S-7)を得る。
製法(3)により合成したイソソルビド誘導体(S-7)1モルと6−ブロモ−2ナフトエ酸1モルとをジシクロヘキシルカルボジイミド等の脱水縮合剤を用いてエステル化反応させイソソルビド誘導体得て、更に無水トリフルオロメタンスルホン酸と反応させて非対称のイソソルビド誘導体(S-12)を得る。
一般式(II-1)〜一般式(II-8)において、r及びsはお互い独立して3〜6の整数が好ましい。
このような化合物の中でも耐熱性や耐久性の点から、一般式(III-2)、一般式(III-5)、一般式(III-6)、一般式(III-9)、一般式(III-10)の化合物が好ましく、一般式(III-2)の化合物がより好ましい。
これらの中でも、一般式(a-2)又は一般式(a-3)で表される化合物を添加が好ましい。u及びvは3〜18が好ましく、4〜16がより好ましく、6〜12が特に好ましい。
さらに本発明の重合性液晶組成物には、重合性官能基を有する化合物であって、液晶性を示さない化合物を添加することもできる。このような化合物としては、通常、この技術分野で高分子形成性モノマーあるいは高分子形成性オリゴマーとして認識されるものであれば特に制限なく使用することができるが、その添加量は組成物として液晶性を呈するように調整する必要がある。
(実施例1)
撹拌装置、冷却器及び温度計を備えた反応容器に3-(p-ヒドロキシフェニル)安息香酸 33.2g(240ミリモル)、ヨウ化カリウム 4g、テトラブチルアンモニウムブロミド 1g、エタノール 400mlを仕込み室温で攪拌した。水酸化ナトリウム 24gの25%水溶液をゆっくり滴下した。滴下終了後、反応容器を50℃に保ち、ベンジルブロミド 50g(288ミリモル)をゆっくり滴下した。滴下終了後、反応容器を更に70℃に加温して更に3時間反応させた。反応終了後、10%塩酸で中和して酢酸エチルで抽出を行い、硫酸ナトリウムで乾燥後、溶媒を濃縮して式(1)に示す化合物を38g合成した。
H−NMR(溶媒:重クロロホルム):δ:4.26−4.10(m,4H), 4.40(m,2H),4.42(s,8H),4.54(m,4H),4.66(m,1H),5.03(m,1H),5.45(m,2H),5.84(d,2H),5.86(m,2H),6.14(m,2H),6.45(d,2H),6.93(m,4H),7.98(d,2H),8.04(d,2H)13C−NMR(溶媒:重クロロホルム):δ:62.0,65.7,66.0,70.7,74.3,78.3,81.1,86.1,114.1,122.3,127.7,131.4,131.7,154.6,162.1,165.5赤外吸収スペクトル(IR)(KBr):2925,2855,1760,1652−1622,809
式(5)で表される化合物は粘調液体であり、他の液晶性化合物との溶解性に優れる。
下記に示すネマチック液晶組成物に1.0%添加して光学顕微鏡より求めるピッチよりHTPを算出した結果、HTP=30と高い値を示した。
撹拌装置、冷却器及び温度計を備えた反応容器にブロモ安息香酸25g(124ミリモル)、イソソルビド 9g(62ミリモル)、ジメチルアミノピリジン 1.8g、ジクロロメタン 200mlを仕込こみ、氷冷バスにて5℃以下に反応容器を保ち、窒素ガスの雰囲気下でジイソプロピルカルボジイミド 18.8g(149ミリモル)をゆっくり滴下した。滴下終了後、反応容器を室温に戻し5時間反応させた。反応液をろ過した後、ろ液に塩化メチレン200mlを加え、10%塩酸水溶液で洗浄し、更に飽和食塩水で洗浄し、有機層を無水硫酸ナトリウムで乾燥させた。溶媒を留去した後、メタノールで目的物を洗浄後、塩化メチレン/メタノールによる再結晶により式(6)に示す化合物25gを得た。
1H−NMR(溶媒:重クロロホルム):δ:1.83(s,8H),4.08(m,4H),4.27(m,8H),4.71(d,1H),5.09(m,1H),5.44(m,2H),5.84(d,2H),6.17(m,2H),6.43(d,2H),6.55(dd,2H),7.60(m,4H),7.72(m,2H),8.04(d,2H),8.10(d,2H)
13C−NMR(溶媒:重クロロホルム):δ:25.2,63.7,64.0,70.5,73.1,74.5,78.4,80.9,85.8,120.3,120.4,127.6,128.0,129.8,130.2,130.3,138.5,138.6,142.7,142.8,162.7,164.4,164.7,165.6,165.8
赤外吸収スペクトル(IR)(KBr):2925,2855,1760,1652−1622,809
(融点)82℃
式(8)で表される化合物は、融点が82℃と低く、他の液晶性化合物との溶解性に優れる。
実施例1と同様にしてHTPを算出した結果、HTP=41と高い値を示した。
(実施例3)
撹拌装置、冷却器、及び温度計を備えた反応容器に実施例2で合成した式(6)に示す化合物26.5g(48.8ミリモル)、ヒドロキシブチルアクリレート 14.6g(126ミリモル)、トリエチルアミン 14g(146ミリモル)、テトラブチルアンモニウムブロミド31g(97ミリモル)、酢酸パラジウム 1g、ジメチルホルムアミド 300mlを仕込み、窒素ガス雰囲気下で反応器を90℃に加熱し反応させた。反応終了後、酢酸エチル、THFを加え、10%塩酸水溶液、純水、飽和食塩水で有機層を洗浄した。溶媒を留去した後、5倍量(重量比)のシリカゲルカラムにより精製を行い式(9)に示す化合物16gを得た。
1H−NMR(溶媒:重クロロホルム):δ:2.67(m,4H),3.02(m,4H),4.04(m,4H),4.34(s,8H),4.66(m,1H),5.04(m,1H),5.40(m,2H),5.84(d,2H),6.15(m,2H),6.44(dd,2H),7.28(m,4H),7.94(d,2H),7.99(d,2H)
13C−NMR(溶媒:重クロロホルム):δ:25.2,63.7,64.0,70.5,73.1,74.5,78.4,80.9,85.8,120.3,120.4,127.6,128.0,129.8,130.2,130.3,138.5,138.6,142.7,142.8,162.7,164.4,164.7,165.6,165.8
赤外吸収スペクトル(IR)(KBr):2925,2855,1760,1652−1622,809
式(11)で表される化合物は粘調液体であり、他の液晶性化合物との溶解性に優れる。
実施例1と同様にしてHTPを算出した結果、HTP=34と高い値を示した。
(実施例4)
撹拌装置、冷却器、及び温度計を備えた反応容器に4-ブロモ-2-フルオロビフェニル30g(120ミリモル)、ジクロロメタン120を加え0℃に冷却する。次いで塩化アルミニム17.6gを加えた後、シュウ酸クロリド16.7gを発熱に気をつけながらゆっくり滴下し、滴下終了後20℃で1時間反応させた。反応終了後、水でシュウ酸クロリドを分解させた後に有機相を飽和食塩水で洗浄、溶媒を留去することにより、式(12)に示す化合物を得た。
1H−NMR(溶媒:重クロロホルム):δ:1.71(m,8H)2.68(m,4H),2.99(m,4H),4.09−4.18(m,12H),4.70(d,1H),5.09(t,1H),5.46(t,1H),5.52(m,1H),5.84(dd,2H),6.11(m,2H),6.37(dd,2H),7.01−7.10(m,4H),7.35−7.41(m,2H),7.59−7.64(m,4H)8.078.15(d,213C−NMR(溶媒:重クロロホルム):δ:25.2,30.3,35.2,63.9,64.1,70.7,74.5,78.5,81.2,115.9,116.2,124.5,128.4,128.9,129.8,129.9,130.5,130.8,166.1,172.5
赤外吸収スペクトル(IR)(KBr):2925,2855,1760,1652−1622,809
(融点)64℃
式(16)で表される化合物は、融点が64℃と低く、他の液晶性化合物との溶解性に優れる。
(比較例1)
撹拌装置、冷却器、及び温度計を備えた反応容器に4-(4-ヒドロキシフェニル)安息香酸 21.4g(100ミリモル)、ヨウ化カリウム 2.5g、テトラブチルアンモニウムブロミド 0.7g、エタノール 400mlを仕込み室温で攪拌した。水酸化ナトリウム 12gの25%水溶液をゆっくり滴下した。滴下終了後、反応容器を50℃に保ち、6-クロロプロパノール 20g(150ミリモル)をゆっくり滴下した。滴下終了後、反応容器を更に70℃に加温して更に3時間反応させた。反応終了後、10%塩酸で中和して酢酸エチルで抽出を行い、硫酸ナトリウムで乾燥後、溶媒を濃縮して式(17)に示す化合物4を22g合成した。
1H−NMR(溶媒:重クロロホルム):δ:1.55−1.45(m,8H),1.71(m,4H),1.83(m,4H),2.66(m,4H),2.96(m,4H),
3.93(m,2H),3.98(m,2H),4.03(s,4H),4.30(t,4H),4.50(t,4H),5.35(s,2H),5.65(dd,2H),5.85(d,2H),5.85(d,2H),6.15(q,2H),6.55(d,2H),7.10(d,4H),7.50(m,4H),8.12(d,4H),8.13(d,4H)
赤外吸収スペクトル(IR)(KBr):2925,2855,1760,1652−1622,809
(融点)>150℃
比較例1記載の式(19)で表される化合物は、本願発明の化合物の特徴となるエステル結合を有するスペーサーを持たない。そのため、融点が高く他の化合物との溶解性にも問題があった。実施例1と同様の液晶組成物でHTPを算出した結果、HTP=33と高い値を示したが、溶解性が悪いために0.5%しか添加できなかった。
(比較例2)
撹拌装置、冷却器及び温度計を備えた反応容器に3−(p-ヒドロキシフェニル)プロピオン酸 20g(120ミリモル)、ヨウ化カリウム 2g、テトラブチルアンモニウムブロミド 0.5g、エタノール 400mlを仕込み室温で攪拌した。水酸化ナトリウム 12gの25%水溶液をゆっくり滴下した。滴下終了後、反応容器を50℃に保ち、ベンジルブロミド 25g(144ミリモル)をゆっくり滴下した。滴下終了後、反応容器を更に70℃に加温して更に3時間反応させた。反応終了後、10%塩酸で中和して酢酸エチルで抽出を行い、硫酸ナトリウムで乾燥後、溶媒を濃縮して式(20)に示す化合物を44g合成した。
1H−NMR(溶媒:重クロロホルム):δ:1.55−1.45(m,8H),1.71(m,4H),1.83(m,4H),2.66(m,4H),2.96(m,4H),3.76(m,2H),3.90(s,4H),4.03(t,4H),4.17(t,4H),4.29(t,1H),4.76(t,1H),5.18(d,2H),5.78(d,2H),6.15(q,2H),6.37(d,2H),6.96(d,4H)7.23(d,4H),7.25(m,4H),8.12(d,4H)
13C−NMR(溶媒:重クロロホルム):δ:25.6,28.4,28.8,30.1,30.2,35.3,35.5,64.3,67.9,73.0,73.8,80.6,85.7,114.0,121.3,121.5,128.3,129.0,130.2,131.9,137.1,137.4,149.2,163.0,164.5,165.9,171.3,171.6
赤外吸収スペクトル(IR)(KBr):2925,2855,1760,1652−1622,809
(融点)79℃
式(25)で表される化合物は、融点が79℃と低く、他の液晶性化合物との溶解性に優れるが、実施例1と同様にしてHTPを算出した結果、HTP=12と低い値であった。
(実施例5) 重合性液晶組成物の調製
以下に示す組成の重合性液晶組成物(組成物1)を調製した。
(実施例6) 重合性液晶組成物の調製
以下に示す組成の重合性液晶組成物(組成物3)を調製した。
(比較例3) 重合性液晶組成物の調製
以下に示す組成の重合性液晶組成物(組成物5)を調製した。
Claims (4)
- 一般式(I)
Y1 は−OCOCH 2 CH 2 −、−OCOOS 3 O−又は−OCO−CH=CH−を表し、
Y 2 は―CH 2 CH 2 COO−、−OS 3 OCOO−又は―CH=CH−COO−を表し、
S3は炭素数2〜6のアルキレン基を表し、
A1及びA4は独立して1,4−フェニレン基及びナフタレン−2,6−ジイル基を表し、
A2及びA3はお互い独立して、1,4−シクロヘキシレン基、1,4−フェニレン基、ナフタレン−2,6−ジイル基、テトラヒドロナフタレン−2,6−ジイル基を表すが、A1、A2、A3及びA4はお互い独立してアルキル基、ハロゲン化アルキル基、アルコキシ基、ハロゲン、シアノ基又はニトロ基により置換されていても良く、
B1及びB2はお互い独立して、−OCH2−、−CH2O−、―COO−、−OCO−、又は単結合を表し、
X1は、−CO−を表し、
X2は、−CO−を表し、
m及びnは0、1又は2を表す。)で表される重合性キラル化合物。 - m及びnの少なくとも一方が0を表す請求項1記載の重合性キラル化合物。
- 請求項1又は2に記載される重合性キラル化合物を含有する液晶組成物。
- 請求項3に記載の液晶組成物を用いた光学異方体。
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