CN101220278A - Non-covalence synthesizing method for light sensing thermotropic liquor supermolecule - Google Patents
Non-covalence synthesizing method for light sensing thermotropic liquor supermolecule Download PDFInfo
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Abstract
The invention discloses a non-covalent synthesis method of a photosensitive thermal liquid crystal supermolecular which puts the azo chromophore ion liquid crystal into the water or the polar solvent to dissolve and then the solution is made; similarly, the sodium hydroxide solution is used for neutralizing till to the neutrality so as to prepare the anion polyelectrolyte solution. Under the violent electromagnetic stirring, the equimolar azo chromophore ion liquid crystal solution is gradually dripped into the polyelectrolyte solution. After the dripping is finished, the stirring continues to lead the compound fully to react and filter. Under the state of the filtration, the supramolecular sedimentation is washed many times by water so as to remove the formed salt and the unreacted compound. The pure photosensitive thermal liquid crystal supermolecular polymer is obtained after the vacuum drying. By adopting the simple method, realizable operation and environmental protection, the compound of the invention is directly separated out from the water solution according to the chemical dosage ratio without needing the subsequent treatment such as the purification. The thermal property, phase behavior and light orientation characteristic of the supermolecular liquid crystal material are regulated by regulating the length of the flexible chain of the ion liquid crystal compound.
Description
Technical field
The present invention relates to the non-covalent synthesis method of a kind of synthetic method of chemical technology field, particularly a kind of photosensitive sensing thermotropic liquor supermolecule.
Background technology
The function photochromics has very wide using value and prospect at high-technology fields such as liquid-crystal display, information storage, photoswitches, therefore the exploitation of novel photochromics and the focus that is designed to scientific circles and industrial community common concern.The traditional preparation process photochromics is mainly used classical covalent chemical synthetic method.Now developed and synthesized side chain, main chain and photosensitive high polymer such as hyperbranched, but the products therefrom productive rate is very low, process is loaded down with trivial details, and cost is higher, and utilizes some to pollute heavier chemical solvents in the process more.In contrast to this, the fairly simple environmental protection of photosensitive micromolecular method of mixing in the polymer, cost is also lower, but the adulterating method consistency is poor, limited the content of photosensitive group, and the photosensitive property instability, therefore the design of the photosensitive functional materials of various high-performance with synthetic on run into bottleneck.By non-covalent self-assembling method promptly by secondary action for example H key, coordinate bond, acid-base function especially ionization carry out functional materials design, become the strategic forward position of current functional materials research.Recently, supramolecule self-assembly research is flourish, comprise Polymer Systems, organic inorganic hybridization system, living things system etc., but mainly concentrate on constructing or the preparation of hybrid material layer by layer of physical aspect in the solvent, pattern, and also just rise based on the self-assembly research of molecular functionization.The construction unit that the ion construction from part utilizes electrostatic interaction will have opposite charges combines, therefore the structure of mixture can select suitable functional structure unit to realize as required, and can therefore can be used to the synthetic colourful sophisticated functions material of design with multiple interesting function hydridization by a step construction from part together.
Find through literature search prior art, " Comblike Liquid-Crystalline Polymers fromIonic Complexation of Dendronized Polymers and Lipids " (branch-shape polymer and the compound preparation pectination of the lipid ion liquid crystalline polymers) that R.Canilho etc. delivered on 2882 pages of " Macromolecules " (macromole) 2007 40 phases, this article utilizes hyperbranched amino end group cationic polymers and alkyl sodium sulfonate table agent ion alive composite methods to prepare pectination liquid crystal supramolecule, and the liquid crystal phase of gained supramolecular complex carried out systematic study, but functionalization and application facet do not relate to; People such as C.F.J.Faul has reported with the method for ion self-assembly at the Adv.Mater. magazine and has constructed low-molecular-weight photosensitive liquid crystal supramolecule material in addition, but film-forming properties, solvent resistance are not as macromolecular material.In a word, the supramolecule package technique is used for the design of functional materials, causes people's attention more and more, and does not appear in the newspapers as yet with synthetic and the research of light orientation characteristic based on the design that the ion self-assembling method carries out photosensitive sensing thermotropic liquor supermolecule.
Summary of the invention
The objective of the invention is at the deficiencies in the prior art, a kind of non-covalent synthesis method of photosensitive sensing thermotropic liquor supermolecule is provided, make it solve the background technology deficiency, and can also be as required the length of flexible chain by regulating assembly ion liquid crystal regulate and control thermal characteristics, phase behavior and the light orientation characteristic of light sensing supermolecule material.
The present invention is achieved by the following technical solutions, the present invention includes following steps:
(1) takes by weighing in the water-soluble or polar solvent of azo ion liquid crystal, stir azo ion liquid crystal is dissolved fully;
(2) take by weighing in the water-soluble or polar solvent of anionic polyelectrolyte, stir, anionic polyelectrolyte is dissolved fully, be neutralized to neutrality with aqueous sodium hydroxide solution then;
(3) the poly-polyelectrolyte solution of the negatively charged ion that step (2) is made splashes in the azo ion liquid crystal solution that stirs, and the amount of splashing into waits the mole positive and negative charge by the two to be determined than calculating, and after dropwising, continues to stir;
(4) the supramolecule product that obtains of suction filtration separating step (3),, and with product under the suction filtration state repeatedly washing or polar solvent wash, to remove the small molecule salt of assembly and generation before the unreacted fully, then with isolate vacuum-drying.
In the step (1), whipping temp is 20 ℃-60 ℃, and the concentration of dissolving back azo ion liquid crystal is 1g/L-20g/L.
In the step (1), described azo ion liquid crystal, its preparation method: at first the diazonium salt legal system gets hydroxyazobenzene, and hydroxyazobenzene and dibromo alkane reaction connect the alkyl chain flexible portion then, and last and Trimethylamine 99 react that to carry out end group quaternized.The flexible spacer of described azo ion liquid crystal promptly holds the methylene radical between ammonium and the nitrogen benzide to be respectively 4 carbon, 6 carbon, 8 carbon and 12 carbon.
In the step (2), at room temperature stir, dissolving back anionic polyelectrolyte concentration is 5g/L-80g/L, and the aqueous sodium hydroxide solution with 1mol/L-5mol/L is neutralized to neutrality then, and the molecular weight of anionic polyelectrolyte is 20000-1000000.Anionic polyelectrolyte is commercialization polyelectrolyte such as polyacrylic acid, polyethylene benzene sulfonic acid sodium salt.
In the step (3), described vigorous stirring, its rotating speed is greater than 1000r/min; Described continuation is stirred, and its time is 10 minutes-60 minutes.
In the step (4), described separation supramolecule product is meant the method with filter membrane suction filtration separation of 0.45-5 μ m microvoid or centrifugation.
In the step (4), described with isolate vacuum-drying, be meant: with isolate in 40 ℃ of-80 ℃ of vacuum-dryings 12 hours-48 hours.
The used water of the present invention is the secondary redistilled water, and polar solvent is ethanol, methyl alcohol or acetone, or the mixed solvent of water and these solvents.
The photosensitive liquid crystal supramolecule product that the present invention obtains is the thermotropic liquid crystal phase, and the polarized light microscopy photo in heating and the temperature-fall period shows that reversible phase and texture change; Small-angle scattering data presentation liquid crystal phase microstructure presents the different lamellar phase of d spacing according to the methene chain gap length.With the polarisation data always, a series of reversible phase transformation of DSC data presentation peak be the more important thing is and can be regulated its thermal characteristics by the length of regulating the flexible spacer methylene moiety.The heat decomposition temperature of such ionic bonding liquid crystal supramolecule material of thermogravimetric analysis data presentation illustrates to have thermostability preferably at 200-250 ℃, satisfies the application requiring of photochromics.In addition, this photosensitive liquid crystal supramolecule is water insoluble, ethanol, methyl alcohol, acetone and non-polar solvent (as toluene, hexanaphthene, normal heptane etc.), dissolves in chloroform, DMF and DMSO etc., but good by the method film forming and the film properties of spin coating.Ps pulsed laser and ns pulsed laser with 355nm scans the optical anisotropy surface that can obtain molecular chain orientation, and the polarization ultraviolet shows its dichroic ratio between 4-30, is higher than general covalency azo liquid crystal high polymer material (1-10); Can successfully be used for the small molecules liquid crystal aligning.Photosensitive sensing thermotropic liquor supermolecule synthetic method of the present invention utilizes a step package technique to carry out the synthetic and design of function photo sensitive polymeric materials.Compare with the covalency synthesis method, method is simple, operation is easy to realize, reaction system is generally the aqueous solution, environmental friendliness, the assembling product is directly separated out from the aqueous solution by chemical dosage ratio, need not subsequent disposal such as purification, and can pass through the performance of the flexible goal of regulation and control supramolecule of the performance material of adjusting assembly as required.Aspect the high molecular synthetic and performance regulation and control of the sophisticated functions that the present invention is difficult to realize in the covalency synthesis method, good application prospects is arranged.
Description of drawings
Fig. 1 is the synthetic schemes of embodiment 1-4 azo ion liquid crystal assembly.
Fig. 2 is the DSC curve that embodiment 1 obtains photosensitive liquid crystal supramolecule material PAZO12.
Fig. 3 is the polarization uv atlas that embodiment 1 obtains the supramolecule optical alignment film of photosensitive liquid crystal PAZO12.
Fig. 4 is that embodiment 2 obtains the polarization Photomicrograph of photosensitive liquid crystal supramolecule PAZO4 optical alignment film as the liquid crystal cell of small molecules liquid crystal aligning layer.
Wherein: the upper substrate of liquid crystal cell all adopts polyimide (PI) substrate of mechanical friction to do reference.
Concrete embodiment
Below in conjunction with accompanying drawing embodiments of the invention are elaborated: present embodiment is being to implement under the prerequisite with the technical solution of the present invention, provided detailed embodiment and concrete operating process, but protection scope of the present invention is not limited to following embodiment.
Embodiment 1
(1) (0.05mol 6.16g) is dissolved in the hydrochloric acid of 50mL 3mol/L, and dissolving is placed in the ice-water bath fully with the 4-anisidine.Keep reacting liquid temperature under 5 ℃, under induction stirring, dropwise add 10ml (5mol/L) sodium nitrite in aqueous solution, after dropwising 5 minutes, the sodium phenylate solution that dropwise adds 25mL (2mol/L) again, the hcl acidifying that the back adds 1mol/L that finishes causes neutrality, after filtration, washing, dry must be to methoxyl group hydroxyazobenzene 1.With 1 (6.85g, 0.03mol), 1, and the 12-dibromo-dodecane (20g, 0.06mol), salt of wormwood (4.2g, 0.03mol) adding the 150ml 24h that refluxes in the acetone, filtered while hot then is after filtrate is reclaimed and removed most of acetone by underpressure distillation, add sherwood oil (30-60 ℃) precipitated product, filtration drying gets ten dibromo alkoxyl group mabs 2.0.01mol 2 is dissolved in the 25mL dehydrated alcohol, adds the Trimethylamine 99 alcoholic solution backflow 24h of 5mL 33% after the heating for dissolving, distillation is removed solvent seasoning and is got azo ion liquid crystal ((4-methoxyl group nitrogen benzide oxygen) dodecyl) trimethylammonium bromide AZO12.Synthetic schemes is seen Fig. 1.
(2) take by weighing azo ion liquid crystal AZO12 and be dissolved in the water-ethanol (V: V, 5: 5), stirring is dissolved it fully under 50 ℃, and the concentration of ion liquid crystal is 6g/L.
(3) take by weighing in the water-soluble or polar solvent of polyacrylic acid, at room temperature stir, it is dissolved fully, strength of solution is 20g/L.Aqueous sodium hydroxide solution with 2mol/L is neutralized to neutrality then.The polyacrylic acid molecular weight is: 600000-1000000.
(4) sodium polyacrylate solution that step (2) is made splashes in the azo ion liquid crystal AZO12 solution of vigorous stirring, and the amount of splashing into waits the mole positive and negative charge by the two and determines than calculating; After dropwising, continue to stir 20 minutes;
(5) separate the supramolecule product with 3 μ m microvoid filter membrane suction filtrations, and with product repeatedly washing under the suction filtration state, to remove the small molecule salt NaBr of assembly and generation before the unreacted fully.Then with isolate in 70 ℃ of vacuum-drying 24h.
Fig. 2 has provided the DSC curve of the photosensitive liquid crystal supramolecule material PAZO12 that makes, can be observed a series of reversible phase transformations.As can be seen from Figure 3, with behind the pulse laser irradiation of 355nm, be far longer than the absorption that is parallel on the laser polarization direction perpendicular to the absorption of laser polarization direction, illustrate that the azo molecules side chain has carried out oriented along laser polarization direction, maximum dichroism reaches 30.
Embodiment 2
(1) it is soluble in water to take by weighing azo ion liquid crystal ((4-methoxyl group nitrogen benzide oxygen) butyl) trimethylammonium bromide AZO4 (concrete synthetic method with example 1), stirs down at 40 ℃ it is dissolved fully, and the concentration of ion liquid crystal is 10g/L.
(2) it is soluble in water to take by weighing polyacrylic acid, at room temperature stirs, and it is dissolved fully, and strength of solution is 15g/L.Aqueous sodium hydroxide solution with 1mol/L is neutralized to neutrality then.The polyacrylic acid molecular weight is 600000-1000000.
(3) sodium polyacrylate solution that step (2) is made splashes in the azo ion liquid crystal AZO4 solution of vigorous stirring, and the amount of splashing into waits the mole positive and negative charge by the two and determines than calculating; After dropwising, continue to stir 30 minutes;
(4) use whizzer with 3000r/min rotating speed centrifugation 15 minutes, pour out supernatant, and, repeat above-mentioned centrifugally operated behind the precipitated product water redispersion.5 times so repeatedly, to remove the small molecule salt NaBr of assembly and generation before the unreacted fully.Then with isolate in 50 ℃ of vacuum-drying 24h.
Heat is analyzed and the alternating temperature polarized light microscopy can be observed a series of reversible phase transformations of PAZO4, and the transformation temperature in the heat-processed is respectively 67 ℃ and 92 ℃.Small-angle scattering is analyzed the PAZO4 that shows anneal and at room temperature is laminar nano mesomorphic phase structure.This material presents light orientation characteristic preferably, and with behind the pulse laser irradiation of 355nm, dichroism is 4.6 to the maximum.Fig. 4 shows that the liquid crystal cell of being assembled by the polyimide substrate of this supramolecule alignment films and friction is the light and shade field variation that 90 degree are the cycle under orthogonal polarizing microscope, illustrate the small molecules liquid crystal has been realized even orientation.
Embodiment 3
(1) take by weighing in azo ion liquid crystal ((the 4-methoxyl group nitrogen benzide oxygen) octyl group) trimethylammonium bromide (AZO8) (concrete synthetic method is with example 1) water-soluble-acetone (V: V, 7: 3), stirring is dissolved it fully under 50 ℃, and the concentration of ion liquid crystal is 5g/L.
(2) it is soluble in water to take by weighing polyethylene benzene leech acid sodium, at room temperature stirs, and it is dissolved fully, and strength of solution is 20g/L.
(3) the polyethylene benzene leech acid sodium solution that step (2) is made splashes in the azo ion liquid crystal AZO8 solution of vigorous stirring, and the amount of splashing into waits the mole positive and negative charge by the two and determines than calculating; After dropwising, continue to stir 30 minutes;
(4) separate the supramolecule product with 3 μ m microvoid filter membrane suction filtrations, and with product repeatedly washing under the suction filtration state, to remove the small molecule salt NaBr of assembly and generation before the unreacted fully.Then with isolate in 60 ℃ of vacuum-drying 12h.
Heat is analyzed and the alternating temperature polarized light microscopy can be observed the phase transformation of PAZO8-series reversible.Small-angle scattering is analyzed under the PAZO8 room temperature that shows anneal and is laminar nano mesomorphic phase structure.This material presents light orientation characteristic preferably, behind the pulse laser irradiation with 355nm, absorption perpendicular to laser polarization direction is far longer than the absorption that is parallel on the laser polarization direction, illustrates that the azo molecules side chain has carried out oriented along laser polarization direction, and maximum dichroic ratio reaches 12.
Embodiment 4
(1) takes by weighing azo ion liquid crystal ((4-methoxyl group nitrogen benzide oxygen) hexyl) trimethylammonium bromide (AZO6) (concrete synthetic method is with example 1) and be dissolved in water-methanol (V: V, 7: 3) in, stirring is dissolved it fully under 40 ℃, and the concentration of ion liquid crystal is 10g/L.
(2) it is soluble in water to take by weighing polyacrylic acid, at room temperature stirs, and it is dissolved fully, and strength of solution is 10g/L.Aqueous sodium hydroxide solution with 2mol/L is neutralized to neutrality then.The polyacrylic acid molecular weight is 600000-1000000.
(3) sodium polyacrylate solution that step (2) is made splashes in the azo ion liquid crystal AZO6 solution of vigorous stirring, and the amount of splashing into waits the mole positive and negative charge by the two and determines than calculating; After dropwising, continue to stir 40 minutes;
(4) separate the supramolecule product with 4 μ m microvoid filter membrane suction filtrations, and with product repeatedly washing under the suction filtration state, to remove the small molecule salt NaBr of assembly and generation before the unreacted fully.Then with isolate in 50 ℃ of vacuum-drying 24h.
Heat is analyzed and the alternating temperature polarized light microscopy can be observed a series of reversible phase transformations of PAZO6, and the transformation temperature in the heat-processed is respectively 66 ℃ and 80 ℃.Small-angle scattering is analyzed under the PAZO6 room temperature that shows anneal and is laminar nano mesomorphic phase structure.This material presents light orientation characteristic preferably, and with behind the pulse laser irradiation of 355nm, dichroism is 5 to the maximum.
Claims (10)
1. the non-covalent synthesis method of a photosensitive sensing thermotropic liquor supermolecule is characterized in that, comprises the steps:
(1) takes by weighing in the water-soluble or polar solvent of azo ion liquid crystal, stir azo ion liquid crystal is dissolved fully;
(2) take by weighing in the water-soluble or polar solvent of anionic polyelectrolyte, stir, anionic polyelectrolyte is dissolved fully, be neutralized to neutrality with aqueous sodium hydroxide solution then;
(3) the anionic polyelectrolyte solution that step (2) is made splashes in the azo ion liquid crystal solution that stirs, and the amount of splashing into waits the mole positive and negative charge by the two to be determined than calculating, and after dropwising, continues to stir;
(4) the supramolecule product that obtains of suction filtration separating step (3), and with product under the suction filtration state repeatedly washing or polar solvent wash, to remove the small molecule salt of assembly and generation before the unreacted fully, then with isolate vacuum-drying.
2. the non-covalent synthesis method of photosensitive sensing thermotropic liquor supermolecule according to claim 1 is characterized in that, in the step (1), whipping temp is 20 ℃-60 ℃, and the concentration of dissolving back azo ion liquid crystal is 1g/L-20g/L.
3. the non-covalent synthesis method of photosensitive sensing thermotropic liquor supermolecule according to claim 1 and 2, it is characterized in that, described azo ion liquid crystal, its preparation method: at first the diazonium salt legal system gets hydroxyazobenzene, hydroxyazobenzene and dibromo alkane reaction connect the alkyl chain flexible portion then, and last and Trimethylamine 99 react that to carry out end group quaternized.
4. the non-covalent synthesis method of photosensitive sensing thermotropic liquor supermolecule according to claim 1 and 2 is characterized in that, the flexible spacer of described azo ion liquid crystal promptly holds the methylene radical between ammonium and the nitrogen benzide to be respectively 4 carbon, 6 carbon, 8 carbon and 12 carbon.
5. the non-covalent synthesis method of photosensitive sensing thermotropic liquor supermolecule according to claim 1, it is characterized in that, in the step (2), at room temperature stir, dissolving back anionic polyelectrolyte concentration is 5g/L-80g/L, aqueous sodium hydroxide solution with 1mol/L-5mol/L is neutralized to neutrality then, and the molecular weight of anionic polyelectrolyte is 20000-1000000.
6. the non-covalent synthesis method of photosensitive sensing thermotropic liquor supermolecule according to claim 1 or 5 is characterized in that anionic polyelectrolyte is polyacrylic acid, polyethylene benzene sulfonic acid sodium salt.
7. the non-covalent synthesis method of photosensitive sensing thermotropic liquor supermolecule according to claim 1 is characterized in that, in the step (3), and the azo ion liquid crystal solution of described stirring, its mixing speed is greater than 1000r/min; Described continuation is stirred, and its time is 10 minutes-60 minutes.
8. the non-covalent synthesis method of photosensitive sensing thermotropic liquor supermolecule according to claim 1 is characterized in that, in the step (4), described separation supramolecule product is meant the method with filter membrane suction filtration separation of 0.45-5 μ m microvoid or centrifugation.
9. according to the non-covalent synthesis method of claim 1 or 8 described photosensitive sensing thermotropic liquor supermolecules, it is characterized in that, described in the step (4) with isolate vacuum-drying, be meant: with isolate in 40 ℃ of-80 ℃ of vacuum-dryings 12 hours-48 hours.
10. the non-covalent synthesis method of photosensitive sensing thermotropic liquor supermolecule according to claim 1 is characterized in that used water is the secondary redistilled water, and polar solvent is ethanol, methyl alcohol or acetone, or the mixed solvent of water and these solvents.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101935368A (en) * | 2010-09-27 | 2011-01-05 | 上海交通大学 | Composite method of liquid crystal supermolecule material containing double photosensitive units |
| CN101974337A (en) * | 2010-09-28 | 2011-02-16 | 吉林大学 | Novel room-temperature cation liquid crystal material |
| CN102492153A (en) * | 2011-11-15 | 2012-06-13 | 华东理工大学 | Preparation method of photosensitive hydrogel |
| CN105254528A (en) * | 2015-10-12 | 2016-01-20 | 上海交通大学 | Synthesis of diamine monomer with azo and polyimide prepared from diamine monomer |
| WO2019157834A1 (en) * | 2018-02-13 | 2019-08-22 | 京东方科技集团股份有限公司 | Composite liquid crystal layer, preparation method therefor, display panel and display device |
| CN111748323A (en) * | 2020-07-22 | 2020-10-09 | 江南大学 | Preparation method and application of optical energy storage phase change material based on azobenzene |
| CN112251240A (en) * | 2020-10-20 | 2021-01-22 | 东北大学 | Quaternary ammonium salt ionic liquid crystal polymer with temperature control electronic switch performance and preparation method and application thereof |
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2007
- 2007-12-20 CN CNA2007101725874A patent/CN101220278A/en active Pending
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101935368A (en) * | 2010-09-27 | 2011-01-05 | 上海交通大学 | Composite method of liquid crystal supermolecule material containing double photosensitive units |
| CN101974337A (en) * | 2010-09-28 | 2011-02-16 | 吉林大学 | Novel room-temperature cation liquid crystal material |
| CN102492153A (en) * | 2011-11-15 | 2012-06-13 | 华东理工大学 | Preparation method of photosensitive hydrogel |
| CN105254528A (en) * | 2015-10-12 | 2016-01-20 | 上海交通大学 | Synthesis of diamine monomer with azo and polyimide prepared from diamine monomer |
| WO2019157834A1 (en) * | 2018-02-13 | 2019-08-22 | 京东方科技集团股份有限公司 | Composite liquid crystal layer, preparation method therefor, display panel and display device |
| CN111748323A (en) * | 2020-07-22 | 2020-10-09 | 江南大学 | Preparation method and application of optical energy storage phase change material based on azobenzene |
| CN112251240A (en) * | 2020-10-20 | 2021-01-22 | 东北大学 | Quaternary ammonium salt ionic liquid crystal polymer with temperature control electronic switch performance and preparation method and application thereof |
| CN112251240B (en) * | 2020-10-20 | 2022-04-12 | 东北大学 | Quaternary ammonium salt ionic liquid crystal polymer with temperature control electronic switch performance and preparation method and application thereof |
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