CN114573599A - Photoisomerizable chiral molecules and application thereof in realizing color liquid crystal film patterning - Google Patents
Photoisomerizable chiral molecules and application thereof in realizing color liquid crystal film patterning Download PDFInfo
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 127
- 238000000059 patterning Methods 0.000 title abstract description 16
- 239000002019 doping agent Substances 0.000 claims abstract description 50
- 239000000203 mixture Substances 0.000 claims abstract description 37
- 239000000178 monomer Substances 0.000 claims abstract description 35
- 238000002360 preparation method Methods 0.000 claims abstract description 25
- 239000011248 coating agent Substances 0.000 claims abstract description 23
- 238000000576 coating method Methods 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 23
- 238000010438 heat treatment Methods 0.000 claims abstract description 16
- 238000001035 drying Methods 0.000 claims abstract description 12
- 230000009471 action Effects 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 45
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 20
- 238000005286 illumination Methods 0.000 claims description 16
- -1 4- [ (trans-4-butylcyclohexyl) methoxy ] -4' -ethoxy-2, 2',3,3' -tetrafluoro-1, 1 '-biphenyl Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 238000007699 photoisomerization reaction Methods 0.000 claims description 8
- 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 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229960002479 isosorbide Drugs 0.000 claims description 5
- UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 claims description 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 2
- WTOUYJXPUNLWSZ-UHFFFAOYSA-N 2,4-diethyl-1,3-thiazole 1-oxide Chemical compound C(C)C=1S(C=C(N1)CC)=O WTOUYJXPUNLWSZ-UHFFFAOYSA-N 0.000 claims description 2
- ITGBGBCZKSIVQW-UHFFFAOYSA-N 2,6-difluoro-4-(5-propylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCC)=CN=C1C1=CC(F)=C(C#N)C(F)=C1 ITGBGBCZKSIVQW-UHFFFAOYSA-N 0.000 claims description 2
- WPEZEJLXLRBUSR-UHFFFAOYSA-N 2-fluoro-4-[4-(4-propylphenyl)phenyl]benzonitrile Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(C=2C=C(F)C(C#N)=CC=2)C=C1 WPEZEJLXLRBUSR-UHFFFAOYSA-N 0.000 claims description 2
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 claims description 2
- 239000005212 4-Cyano-4'-pentylbiphenyl Substances 0.000 claims description 2
- HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 claims description 2
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 2
- ZKBUNGNDTCOGEU-UHFFFAOYSA-N [3-methyl-4-[4-(4-prop-2-enoyloxybutoxycarbonyloxy)benzoyl]oxyphenyl] 4-(4-prop-2-enoyloxybutoxycarbonyloxy)benzoate Chemical group C=1C=C(OC(=O)C=2C=CC(OC(=O)OCCCCOC(=O)C=C)=CC=2)C(C)=CC=1OC(=O)C1=CC=C(OC(=O)OCCCCOC(=O)C=C)C=C1 ZKBUNGNDTCOGEU-UHFFFAOYSA-N 0.000 claims description 2
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 claims description 2
- 235000012000 cholesterol Nutrition 0.000 claims description 2
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims description 2
- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical compound [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 229940041616 menthol Drugs 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- YLHXLHGIAMFFBU-UHFFFAOYSA-N methyl phenylglyoxalate Chemical compound COC(=O)C(=O)C1=CC=CC=C1 YLHXLHGIAMFFBU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- DOTOVEIVWNKSJT-UHFFFAOYSA-N 1-but-3-enyl-4-[2-(4-but-3-enylphenyl)ethynyl]benzene Chemical compound C1=CC(CCC=C)=CC=C1C#CC1=CC=C(CCC=C)C=C1 DOTOVEIVWNKSJT-UHFFFAOYSA-N 0.000 claims 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003086 colorant Substances 0.000 description 5
- 239000004988 Nematic liquid crystal Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229930016911 cinnamic acid Natural products 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
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- 239000000463 material Substances 0.000 description 2
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
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- 239000003960 organic solvent Substances 0.000 description 2
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- 239000002516 radical scavenger Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- 238000005406 washing Methods 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical group CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KKEUGGZODLCCTR-UHFFFAOYSA-N 3-methyl-5-(trifluoromethyl)-4h-1,2-oxazol-5-ol Chemical compound CC1=NOC(O)(C(F)(F)F)C1 KKEUGGZODLCCTR-UHFFFAOYSA-N 0.000 description 1
- STRJVIVMRXTARL-UHFFFAOYSA-N 4-[3-fluoro-4-(4-propylphenyl)phenyl]benzonitrile Chemical compound C1=CC(CCC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1F STRJVIVMRXTARL-UHFFFAOYSA-N 0.000 description 1
- DZLOUWYGNATKKZ-UHFFFAOYSA-N 4-ethoxycinnamic acid Natural products CCOC1=CC=C(C=CC(O)=O)C=C1 DZLOUWYGNATKKZ-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
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- 230000001939 inductive effect Effects 0.000 description 1
- 230000004298 light response Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
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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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/58—Dopants or charge transfer agents
- C09K19/586—Optically active dopants; chiral dopants
- C09K19/588—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Abstract
The invention relates to a photoinduced heterogeneous chiral molecule and application thereof in realizing patterning of a color liquid crystal film, and relates to the technical field of liquid crystal films. The preparation method of the photo-induced isomerism liquid crystal film comprises the following steps of heating a liquid crystal monomer and a chiral dopant in a solvent under the action of a photoinitiator, completely reacting, coating the mixture on the surface of the film, drying and then illuminating to obtain the photo-induced isomerism liquid crystal film; the chiral dopant is a photo-isomerisable chiral molecule. The preparation method of the photo-induced heterogeneous liquid crystal film is simple, convenient to operate and low in raw material consumption, and the prepared photo-induced heterogeneous liquid crystal film is stable in performance.
Description
Technical Field
The invention relates to the technical field of liquid crystal films, in particular to a photoinduced heterogeneous chiral molecule and application thereof in realizing color liquid crystal film patterning.
Background
With the development of photo-isomerisable chiral molecules, researchers have applied these molecules to the preparation of liquid crystal materials. Among them, cholesteric liquid crystals can selectively reflect light of different wavelengths due to their own helical structure. The wavelength of the corresponding light is determined by the pitch of the helical structure.
The technology of cholesteric liquid crystal formed by different methods is mature so far, and such liquid crystal can be liquid crystal molecules having chirality per se, or can be a supermolecular helical structure in which cholesteric phase is formed by inducing the liquid crystal molecules through a small amount of chiral molecules (namely chiral dopants). A photoisomerization group, such as azobenzene, cinnamic acid, spiropyran and the like, is added into the structure of the chiral dopant, and the change of the screw pitch is completed in a light irradiation mode. However, the system is greatly affected by light and ambient temperature, so that the fixing of cholesteric liquid crystals with different colors is difficult to achieve, and the system for changing the color by using the photo-isomerism characteristic is few, and most of color fixing still stays in the liquid crystal box.
Disclosure of Invention
The technical problem to be solved by the invention is therefore to overcome the problem of the prior art that the presentation of the liquid-crystal mixture is only in the form of a compact liquid-crystal cell.
In order to solve the technical problems, the invention provides a photo-induced heterogeneous chiral molecule and application thereof in realizing color liquid crystal film patterning. Doping chiral photo-isomeric molecules in nematic liquid crystal, mixing thoroughly, and preparing the photo-isomeric liquid crystal film by changing the amount of the photo-isomeric molecules or the illumination time.
The first purpose of the invention is to provide a photo-induced isomeric chiral molecule, the structural formula is as follows,
wherein n is any integer from 0 to 12, and M represents a chiral motif; the chiral motif is selected from isosorbide, binaphthyl, cholesterol, menthol or 2- (4, n-propyl) cyclohexyl;
r is selected from hydrogen, halogen, methyl, ethyl, acetyl or alkoxy.
In one embodiment of the invention, the chiral motif has the following structure,
wherein denotes a chiral center.
The second purpose of the invention is to provide a preparation method of the photo-induced isomeric chiral molecule, which comprises the following steps of reacting alkyl chain substituted cinnamic acid and a chiral element with hydroxyl at the tail end in an organic solvent for 12-24 hours under the action of a water removing agent and a catalyst in a protective atmosphere to obtain the photo-induced isomeric chiral molecule.
In one embodiment of the invention, the water scavenger is 1-ethyl- (3-dimethylaminopropyl) carbodiimide; the catalyst is 4-dimethylamino pyridine; the organic solvent is tetrahydrofuran.
In one embodiment of the invention, the molar ratio of the alkyl chain substituted cinnamic acid, the chiral element with the hydroxyl at the tail end, the water scavenger and the catalyst is 1-2: 0.5-1: 0.6-1.4: 0.057-0.106.
The third purpose of the invention is to provide a preparation method of the photoinduced isomerism liquid crystal film, which comprises the following steps of heating and reacting a liquid crystal monomer and a chiral dopant in a solvent under the action of a photoinitiator completely, coating the mixture on the surface of the film, drying and then illuminating the film to obtain the photoinduced isomerism liquid crystal film; the chiral dopant is the photo-induced isomeric chiral molecule.
In one embodiment of the invention, the liquid crystal monomer is selected from the group consisting of 2 methyl 1, 4 phenylenebis (4- (((4- (acryloyloxy) butoxy) carbonyl) oxy) benzoate), 4-cyano-4 '-pentylbiphenyl, 2-fluoro-4- [4- (4-propylphenyl) phenyl ] benzonitrile, 4 "-ethyl-2' -fluoro-4-propyl terphenyl, 4" -propyl-3, 4, 5-trifluoro-1, 1':4',1 "-terphenyl, 4" -propyl-2 ', 4-difluoro-1, 1':4',1 "-terphenyl, 3' -fluoro-4" -propyl- [1,1':4',1 "-terphenyl ] -4-carbonitrile, 4- [ (trans-4-butylcyclohexyl) methoxy ] -4' -ethoxy-2, 2',3,3' -tetrafluoro-1, 1' -biphenyl, 2, 6-difluoro-4- (5-propyl-2-pyrimidinyl) benzonitrile, one or more of 1-methoxy-4- [ trans-4- [ (1E) -2- [ trans-4- (1E) -1-propen-1-ylcyclohexyl ] ethenyl ] cyclohexyl ] benzene, and 1,1' - (1, 2-ethynyldiyl) bis [4- (3-buten-1-yl) benzene ]; the photoinitiator is 2-methyl-1- (4-methylthiophenyl) -2-morpholine-1-acetone, 4-dimethylamino-ethyl benzoate, 2-isopropyl thioxanthone, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholine phenyl) -1-butanone, 2, 4-diethyl thiazolone, methyl benzoylformate, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, bis (1- (2, 4-difluorophenyl) -3-pyrrolyl) titanocene, phenylbis (2,4, 6-trimethylbenzoyl) phosphine oxide, and one or more of 4-chlorobenzophenone and 4-chlorobenzophenone.
In one embodiment of the invention, the solvent is selected from cyclohexanone and/or ethyl acetate.
In one embodiment of the invention, the mass ratio of the liquid crystal monomer, the chiral dopant and the photoinitiator is 190-: 12-14: 11-13.
In one embodiment of the invention, the temperature of the heating reaction is 50-100 ℃; the heating reaction time is 4-12 min.
In one embodiment of the present invention, the light source for the illumination is an ultraviolet light source.
In one embodiment of the invention, the illumination time of the ultraviolet light source is 0-90 s; the illumination intensity of the ultraviolet light source is 1000-10000mw/cm2。
In one embodiment of the invention, the film is a polyester film.
In one embodiment of the present invention, the polyester film is polyethylene terephthalate, polyurethane, polymethyl methacrylate, or polypropylene terephthalate.
The fourth purpose of the invention is to provide a photo-induced isomerism liquid crystal film prepared by the method.
Compared with the prior art, the technical scheme of the invention has the following advantages:
(1) the photo-isomerism chiral molecule has both photo-isomerism characteristic and chirality. Wherein the chiral molecules interact with the liquid crystal molecules such that the chiral molecules influence the alignment of the assembly. The molecules or groups with the photo-isomerism characteristic are subjected to cis-trans isomerism when being subjected to an ultraviolet/visible light source, so that the spatial structure of the molecules is influenced. The group with the photo-isomerism characteristic is combined with the chiral molecules, and the structures of the molecules are changed in the process of being illuminated by outside light, so that the degree of influence on the arrangement of liquid crystal molecules is different.
(2) The photo-isomerism liquid crystal film provided by the invention introduces molecules with double characteristics (chirality and photo-isomerism) into a liquid crystal system, liquid crystal monomers are self-assembled into a spiral structure, then the spiral structure is twisted to a certain degree through chiral molecules, the pitch of the whole system is changed, the structural color generated based on Bragg reflection (Bragg reflection) is changed due to the change of the pitch, namely the reflection colors of the prepared liquid crystal film are different, wherein oxygen inhibition plays a key role in photo-isomerism, time is provided for photo-isomerism, and the patterning of a color liquid crystal film is realized by using the competition of photo-isomerism and photo-induced polymerization for the first time.
(3) The photoinduced isomerism liquid crystal film is prepared by coating a liquid crystal mixture into the film in a wire rod scraping mode, wherein the liquid crystal mixture can be nematic liquid crystal serving as main liquid crystal, and photoinduced isomerism chiral molecules are doped into the nematic liquid crystal so as to be converted into cholesteric liquid crystal reflecting circularly polarized light. The color of the structural color of the obtained film is changed under the irradiation of ultraviolet light at different time, and the film can be firstly changed in color and then fixed due to oxygen inhibition, and the patterning mode can be directly applied to film application at room temperature. The method for changing the liquid crystal self-assembly structure through the external condition, namely the illumination not only gives full play to the instantaneity of the illumination and the advantages of no side effect, but also promotes the development of novel chiral materials.
(4) The preparation method of the photo-induced heterogeneous liquid crystal film is simple, convenient to operate and low in raw material consumption, and the prepared photo-induced heterogeneous liquid crystal film is stable in performance.
Drawings
In order that the present disclosure may be more readily and clearly understood, reference is now made to the following detailed description of the present disclosure taken in conjunction with the accompanying drawings, in which:
FIG. 1 is a UV-Vis spectrum test chart of a liquid crystal mixture 1 in test example 1 of the present invention.
FIG. 2 shows graded films of different illumination times prepared under the condition of the liquid crystal mixture 1 in test example 1 of the present invention.
FIG. 3 shows films of different colors with different illumination times prepared under the condition of the liquid crystal mixture 1 in test example 1 of the present invention.
FIG. 4 is a polarization microscope photograph of the liquid crystal mixture 1 in test example 2 of the present invention.
FIG. 5 is a diagram of a thin film of a photoisomerization liquid crystal prepared under the condition of the liquid crystal mixture 1 in test example 3 of the present invention.
Detailed Description
The present invention is further described below in conjunction with the following figures and specific examples so that those skilled in the art may better understand the present invention and practice it, but the examples are not intended to limit the present invention.
Example 1
A photo-induced heterogeneous chiral molecule and application thereof in realizing color liquid crystal film patterning specifically comprise the following steps:
the structures of the liquid crystal monomer, the chiral dopant and the photoinitiator are as follows:
(1) liquid crystal monomer 1
(2) Chiral dopant 1
(3) Photoinitiator 1
Step 1: synthesis of chiral dopant 1 4-methoxy cinnamic acid isosorbide
After 4-methoxycinnamic acid (20g, 112mmol) and isosorbide (7.81g, 53.4mmol) were weighed into a 1000mL three-necked flask, 1-ethyl- (3-dimethylaminopropyl) carbonyldiimine (EDC) (19.91g, 128.2mmol) and 4-Dimethylaminopyridine (DMAP) (1.31g, 10.7mmol) were dissolved in 200mL tetrahydrofuran and added to the flask under N2Stirring for 20h under ambient room temperature conditions. After the reaction, the liquid was poured into ethyl acetate, followed by washing twice with deionized water, once with 1mol/L dilute hydrochloric acid, twice with deionized water, combining the organic phases, rotary evaporating the resulting solution to remove ethyl acetate, and finally, recrystallizing with acetone-methanol to obtain a white powder.
The 4-methoxycinnamic acid isosorbide is characterized on the basis of the following:
1H NMR(400MHz,DMSO-d6)δ7.75–7.60(m,6H),6.99(dq,J＝8.0,3.0Hz,4H),6.54(dd,J＝16.0,13.0Hz,2H),5.28–5.17(m,2H),4.88(t,J＝5.3Hz,1H),4.52(d,J＝4.9Hz,1H),3.99–3.76(m,10H).
step 2: preparation of liquid-crystalline mixture 1
Weighing liquid crystal monomer 1(1g), chiral dopant 1(0.062g) and photoinitiator 1(0.06g) in a glass bottle, adding solvent (cyclohexanone 3.59g and ethyl acetate 0.90g), heating at 50 deg.C for 4min, and mixing well.
Step 3: preparation of photo-induced isomeric liquid crystal film
Selecting a PET film, coating the liquid crystal mixture 1 on the surface of the PET film, blade-coating with a wire bar, drying the solvent, and irradiating the surface of the film with an ultraviolet light source for 5s (the peak irradiation intensity of the light source is 10000 mw/cm)2) And preparing the photo-induced heterogeneous liquid crystal film.
Example 2
A photo-induced heterogeneous chiral molecule and application thereof in realizing color liquid crystal film patterning specifically comprise the following steps:
the structures of the liquid crystal monomer, the chiral dopant and the photoinitiator are as follows:
(1) liquid crystal monomer 1
(2) Chiral dopant 2
(3) Photoinitiator 2
Step 1: synthesis of chiral dopant 2
After 4-ethoxycinnamic acid (20g, 112mmol) and binaphthol (7.81g, 53.4mmol) were weighed into a 1000mL three-necked flask, 1-ethyl- (3-dimethylaminopropyl) carbonyldiimine (EDC) (19.91g, 128.2mmol) and 4-Dimethylaminopyridine (DMAP) (1.31g, 10.7mmol) were dissolved in 300mL tetrahydrofuran and added to the flask in N2Stirring for 20h under ambient room temperature conditions. After the reaction, the liquid was poured into ethyl acetate, followed by washing twice with deionized water, once with 1mol/L dilute hydrochloric acid, twice with deionized water, combining the organic phases, rotary evaporating the resulting solution to remove ethyl acetate, and finally, recrystallizing with acetone-methanol to obtain a white powder.
Step 2: preparation of liquid-crystalline mixture 2
Weighing liquid crystal monomer 1(1g), chiral dopant 2(0.065g) and photoinitiator 2(0.06g) in a glass bottle, adding solvent (cyclohexanone 3.6g and ethyl acetate 0.90g), heating at 100 deg.C for 10min, and mixing well.
Step 3: preparation of photo-induced isomeric liquid crystal film
Selecting a PET film, coating the liquid crystal mixture 2 on the surface of the PET film, blade-coating with a wire bar, drying the solvent, and irradiating the surface of the film with an ultraviolet light source for 5s (the peak irradiation intensity of the light source is 10000 mw/cm)2) And preparing the photoisomerization liquid crystal film.
Example 3
A photo-induced heterogeneous chiral molecule and application thereof in realizing color liquid crystal film patterning specifically comprise the following steps:
the structures of the liquid crystal monomer, the chiral dopant and the photoinitiator are as follows:
(1) liquid crystal monomer 2
(2) Chiral dopant 1
(3) Photoinitiator 1
Step 1: synthesis of chiral dopant 1 the same as in example 1
Step 2: preparation of liquid-crystalline mixture 3
Weighing liquid crystal monomer 2(1g), chiral dopant 1(0.062g) and photoinitiator 1(0.06g) in a glass bottle, adding solvent (cyclohexanone 3.59g and ethyl acetate 0.90g), heating at 50 deg.C for 4min, and mixing well.
Step 3: preparation of photo-induced isomeric liquid crystal film
Selecting a PET film, coating the liquid crystal mixture 3 on the surface of the PET film, carrying out blade coating by using a wire rod, drying the solvent, and irradiating the surface of the film for 5s, 10s, 15s and 20s by using an ultraviolet light source (the peak irradiation intensity of the light source is 10000 mw/cm)2) And preparing the photo-induced heterogeneous liquid crystal film.
Example 4
A photo-induced heterogeneous chiral molecule and application thereof in realizing color liquid crystal film patterning specifically comprise the following steps:
the structures of the liquid crystal monomer, the chiral dopant and the photoinitiator are as follows:
(1) liquid crystal monomer 2
(2) Chiral dopant 1
(3) Photoinitiator 3
Step 1: synthesis of chiral dopant 1 the same as in example 1
Step 2: preparation of the liquid-crystalline mixture 4
Weighing liquid crystal monomer 2(2g), chiral dopant 1(1.32g) and photoinitiator 3(0.12g) in a glass bottle, adding solvent (cyclohexanone 3.59g and ethyl acetate 0.90g), heating at 50 deg.C for 4min, and mixing well.
Step 3: preparation of photo-induced isomeric liquid crystal film
Selecting a PET film, coating the liquid crystal mixture 4 on the surface of the PET film, blade-coating with a wire bar, drying the solvent, and irradiating the surface of the film with ultraviolet light for 5s, 10s, 15s and 20s (the peak irradiation intensity of the light source is 10000 mw/cm)2) And preparing the photo-induced heterogeneous liquid crystal film.
Example 5
A photo-induced heterogeneous chiral molecule and application thereof in realizing color liquid crystal film patterning specifically comprise the following steps:
the structures of the liquid crystal monomer, the chiral dopant and the photoinitiator are as follows:
(1) liquid crystal monomer 2
(2) Chiral dopant 2
(3) Photoinitiator 4
Step 1: synthesis of chiral dopant 2 the same as in example 2
Step 2: preparation of liquid-crystalline mixture 5
Weighing liquid crystal monomer 2(1g), chiral dopant 2(0.062g) and photoinitiator 4(0.06g) in a glass bottle, adding solvent (cyclohexanone 3.59g and ethyl acetate 0.90g), heating at 100 deg.C for 10min, and mixing well.
Step 3: preparation of photo-induced heterogeneous liquid crystal film
Selecting a PET film, coating the liquid crystal mixture 5 on the surface of the PET film, blade-coating with a wire bar, drying the solvent, and irradiating the film surface with ultraviolet light for 5s, 10s, 15s and 20s (the peak irradiation intensity of the light source is 5000 mw/cm)2) And preparing the photo-induced heterogeneous liquid crystal film.
Example 6
A photoinduced isomerism chiral molecule and application thereof in realizing color liquid crystal film patterning specifically comprise the following steps:
the structures of the liquid crystal monomer, the chiral dopant and the photoinitiator are as follows:
(1) liquid crystal monomer 3
(2) Chiral dopant 1
(3) Photoinitiator 4
Step 1: synthesis of chiral dopant 1 the same as in example 1
Step 2: preparation of the liquid-crystalline mixture 6
Weighing liquid crystal monomer 3(1g), chiral dopant 1(0.06g) and photoinitiator 4(0.06g) in a glass bottle, adding solvent (cyclohexanone 3.59g and ethyl acetate 0.90g), heating at 50 deg.C for 4min, and mixing well.
Step 3: preparation of photo-induced heterogeneous liquid crystal film
Selecting a PET film, coating the liquid crystal mixture 6 on the surface of the PET film, blade-coating with a wire bar, drying the solvent, and irradiating the surface of the film with ultraviolet light for 5s, 10s, 15s and 20s (the peak irradiation intensity of the light source is 1000 mw/cm)2) And preparing the photo-induced heterogeneous liquid crystal film.
Example 7
A photo-induced heterogeneous chiral molecule and application thereof in realizing color liquid crystal film patterning specifically comprise the following steps:
the structures of the liquid crystal monomer, the chiral dopant and the photoinitiator are as follows:
(1) liquid crystal monomer 3
(2) Chiral dopant 2
(3) Photoinitiator 3
Step 1: synthesis of chiral dopant 2 the same as in example 2
Step 2: preparation of the liquid-crystalline mixture 7
Weighing liquid crystal monomer 3(1g), chiral dopant 2(0.064g) and photoinitiator 3(0.06g) in a glass bottle, adding solvent (cyclohexanone 3.59g and ethyl acetate 0.90g), heating at 50 deg.C for 4min, and mixing well.
Step 3: preparation of photo-induced isomeric liquid crystal film
Selecting a PET film, coating the liquid crystal mixture 7 on the surface of the PET film, carrying out blade coating by using a wire rod, drying the solvent, and irradiating the surface of the film for 5s, 10s, 15s and 20s by using an ultraviolet light source (the peak irradiation intensity of the light source is 1000 mw/cm)2) And preparing the photo-induced heterogeneous liquid crystal film.
Example 8
A photo-induced heterogeneous chiral molecule and application thereof in realizing color liquid crystal film patterning specifically comprise the following steps:
the structures of the liquid crystal monomer, the chiral dopant and the photoinitiator are as follows:
(1) liquid crystal monomer 3
(2) Chiral dopant 2
(3) Photoinitiator 1
Step 1: synthesis of chiral dopant 2 the same as in example 2
Step 2: preparation of the liquid-crystalline mixture 8
Weighing liquid crystal monomer 3(1g), chiral dopant 2(0.065g) and photoinitiator 1(0.06g) in a glass bottle, adding solvent (cyclohexanone 3.59g and ethyl acetate 0.90g), heating at 50 deg.C for 4min, and mixing well.
Step 3: preparation of photo-induced heterogeneous liquid crystal film
Selecting a PET film, coating the liquid crystal mixture 8 on the surface of the PET film, carrying out blade coating by using a wire rod, drying the solvent, and irradiating the surface of the film for 5s, 10s, 15s and 20s by using an ultraviolet light source (the peak irradiation intensity of the light source is 1000 mw/cm)2) And preparing the photo-induced heterogeneous liquid crystal film.
Comparative example
The structures of the liquid crystal monomer, the chiral dopant and the photoinitiator are as follows:
(1) liquid crystal monomer 1
(2) Chiral dopant 1
(3) Photoinitiator 1
Step 1: synthesis of chiral dopant 1 the same as in example 1
Step 2: preparation of liquid-crystalline mixtures
Weighing liquid crystal monomer 3(1g), chiral dopant 2(0.062g) and photoinitiator 3(0.06g) in a glass bottle, adding solvent (cyclohexanone 3.59g and ethyl acetate 0.90g), heating at 100 deg.C for 10min, and mixing well.
Step 3: preparation of liquid crystal films
Selecting a PET film, coating the liquid crystal mixture on the surface of the PET film, blade-coating with a wire bar, drying the solvent, and irradiating the surface of the film with an ultraviolet light source for 100s (the peak irradiation intensity of the light source is 1000 mw/cm)2) And preparing the liquid crystal film.
The color of the film disappears after the illumination time is too long.
Test example 1
The UV-Vis spectra of the liquid-crystal mixtures 1 obtained in example 1 according to the invention were determined and the results are shown in FIGS. 1 to 3. As can be seen from fig. 1, as the illumination time increases, the reflection wavelength corresponding to the thin film is continuously red-shifted, and the thin film has a photo-isomerism characteristic. FIG. 2 shows that the color of the film gradually red-shifts with the increase of the illumination time of the gradual film prepared under the condition of the liquid crystal mixture 1 and with different illumination time. FIG. 3 liquid crystal mixture 1 and chiral dopant 1 are mixed to prepare films (liquid crystal mixture 1g, chiral dopant 62mg) with different colors and different illumination time.
Test example 2
FIG. 4 shows the results of taking an image of the liquid crystal mixture 1 obtained in example 1 of the present invention by a polarization microscope. As can be seen from the figure, the liquid crystal mixture has a typical oily silk texture, which is a specific texture of cholesteric liquid crystal, and it can be proved that the original nematic liquid crystal has been changed into cholesteric liquid crystal through the induction of chiral dopant, and the cholesteric liquid crystal is uniformly displayed on the film.
Test example 3
FIG. 5 shows a photo-induced isomerism liquid crystal film prepared under the condition of liquid crystal mixture 1, wherein the characters are non-illuminated parts and the background is illuminated parts. The cholesteric liquid crystal film obtained by the blade coating mode has responsiveness to light due to the fact that the chiral dopant contains the photo-isomerism group, the film is placed in a constant temperature system of 80 ℃, and the film is sensitive to light response at a high temperature. Subsequently, the transparent film with the black characters is placed on the film in a parallel illumination atmosphere for 4s, and the obtained film can generate color differences due to illumination differences. Fig. 5 is a green colored film prepared using liquid crystal mixture 1, a transparent film with poem was placed over the film, and then light was applied to obtain a pattern in a green font with an orange background, and finally the obtained pattern was photocured. Thus, patterning of cholesteric liquid crystal films of different colors is achieved.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications of the invention may be made without departing from the spirit or scope of the invention.
Claims (10)
1. A photo-induced isomeric chiral molecule is characterized in that the structural formula is as follows,
wherein n is an integer of 0-12, and M represents a chiral motif; the chiral motif is selected from isosorbide, binaphthyl, cholesterol, menthol or 2- (4, n-propyl) cyclohexyl;
r is selected from hydrogen, halogen, methyl, ethyl, acetyl or alkoxy.
2. The photo-isomerisable chiral molecule according to claim 1, wherein said chiral motif has the following structure,
wherein denotes a chiral center.
3. The preparation method of the photoisomerization liquid crystal film is characterized by comprising the following steps of heating a liquid crystal monomer and a chiral dopant in a solvent under the action of a photoinitiator for complete reaction, coating the mixture on the surface of the film, drying and then illuminating to obtain the photoisomerization liquid crystal film; the chiral dopant is a photo-isomerisable chiral molecule according to claim 1 or 2.
4. The method of claim 3, wherein the liquid crystal monomer is selected from the group consisting of 2 methyl 1, 4 phenylenebis (4- (((4- (acryloyloxy) butoxy) carbonyl) oxy) benzoate), 4-cyano-4 '-pentylbiphenyl, 2-fluoro-4- [4- (4-propylphenyl) phenyl ] benzonitrile, 4 "-ethyl-2' -fluoro-4-propyl terphenyl, 4" -propyl-3, 4, 5-trifluoro-1, 1':4',1 "-terphenyl, 4" -propyl-2 ', 4-difluoro-1, 1':4',1 "-terphenyl, 3' -fluoro-4" -propyl- [1,1': one or more of 4',1 "-terphenyl ] -4-carbonitrile, 4- [ (trans-4-butylcyclohexyl) methoxy ] -4' -ethoxy-2, 2',3,3' -tetrafluoro-1, 1 '-biphenyl, 2, 6-difluoro-4- (5-propyl-2-pyrimidinyl) benzonitrile, 1-methoxy-4- [ trans-4- [ (1E) -2- [ trans-4- (1E) -1-propen-1-ylcyclohexyl ] ethenyl ] cyclohexyl ] benzene, and 1,1' - (1, 2-acetylenediyl) bis [4- (3-buten-1-yl) benzene ]; the photoinitiator is 2-methyl-1- (4-methylthiophenyl) -2-morpholine-1-acetone, 4-dimethylamino-ethyl benzoate, 2-isopropyl thioxanthone, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholine phenyl) -1-butanone, 2, 4-diethyl thiazolone, methyl benzoylformate, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone, bis (1- (2, 4-difluorophenyl) -3-pyrrolyl) titanocene, phenylbis (2,4, 6-trimethylbenzoyl) phosphine oxide, and one or more of 4-chlorobenzophenone and 4-chlorobenzophenone.
5. The method for preparing a photoisomerization liquid crystal film according to claim 3, wherein the solvent is selected from cyclohexanone and/or ethyl acetate.
6. The method for preparing the photo-induced heterogeneous liquid crystal film according to claim 3, wherein the mass ratio of the liquid crystal monomer, the chiral dopant and the photoinitiator is 190-210: 12-14: 11-13.
7. The method for preparing the photoisomerization liquid crystal film according to claim 3, wherein the temperature of the heating reaction is 50-100 ℃; the heating reaction time is 4-12 min.
8. The method of claim 3, wherein the light source is an ultraviolet light source.
9. The method for preparing a photoisomerization liquid crystal film according to claim 8, wherein the irradiation time of the uv light source is 0-90 s; the illumination intensity of the ultraviolet light source is 1000-10000mw/cm2。
10. A photo-isomerisable liquid crystal film obtainable by a process according to any one of claims 3 to 9.
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