CN101521030B - Azobenzol liquid crystal holography storage material and preparation method thereof - Google Patents
Azobenzol liquid crystal holography storage material and preparation method thereof Download PDFInfo
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- CN101521030B CN101521030B CN2009100381375A CN200910038137A CN101521030B CN 101521030 B CN101521030 B CN 101521030B CN 2009100381375 A CN2009100381375 A CN 2009100381375A CN 200910038137 A CN200910038137 A CN 200910038137A CN 101521030 B CN101521030 B CN 101521030B
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Abstract
The invention discloses an azobenzol liquid crystal holography storage material and a preparation method thereof. The material comprises silicon dioxide, a compound containing azobenzol radical and a compound containing liquid crystal radical, wherein mol ratio of the azobenzol radical to the liquid crystal radical is 0.5-10:1. The substrate material used in the azobenzol liquid crystal holographystorage material has a silicon dioxide structure with excellent high-transparency and low scattered power, has lower refractive index, and can obtain high modulation index of the refractive index whe n the substrate material is matched with a photorefractive compound with higher refractive index. Existence of the liquid crystal radical can reinforce the photorefractive effect generated by the azobenzol radical in light, and improve diffraction efficiency, thereby improving information storage capacity; and regular arrangement of the liquid crystal radical cannot be affected by thermal motion and non signal light, so that data storage time can be greatly prolonged. Cis-trans isomers of the azobenzol radical can be converted with each other under radiation of signal light and induce the arrangement of the liquid crystal radical, and data can be repeatedly erased and written.
Description
Technical field
The present invention is used for the new material and the technology of preparing thereof of data storage.
Background technology
Worldwide storage demand is with the speed increase in every year 75%, and huge quantity of information makes people to the data storage means of high density, high transmission rates the endless pursuit of being close to be arranged.Traditional memory technology, though updating as magnetic storage, conventional optical disc storage, semiconductor storage etc., these storage means are just progressively near its physics limit.The CD of permanent recording is made up of a series of pit and grooves that are etched in the surface, can rewrite surface crystallizationization/noncrystallineization that CD adopts thin amorphous layer, and information wherein also can be optically read with numerical coding.Disk is equally with the mode storing digital information of different magnetic domains of arranging on the magnetic medium surface.Based on data storage of two dimension (2D) storer such as the theoretical limit that optical read/write pit, groove or magnetic domain are reaching given material.At first, the size of pit and groove is reduced to several nanometers and may reaches 10
10-10
12Bits/mm
2The limit.But a solution is subjected to the restriction of precision optical machinery with high costs inevitably like this, needs special environment (high vacuum or pure liquid state), the most important thing is because the inherent shortcoming of 2D technology.Read continuously very slowly, the access time that causes storing data is long especially.
With respect to above-mentioned two dimension (2D) data storage, can under the condition of equal volume, obtain high data capacity as the holographic storage technology of three-dimensional (3D) data storage.The holographic optical storage utilizes the interference figure of the stack generation of two coherent laser beams to store numerical data according to the principle of holography.Wherein, first light beam is " information carrying beam ", by the information that spatial light modulator is modulated and carrying is write down with the data page form.Second light beam is " reference beam ", and load information can not form interference figure with first light beam is crossing.The interference figure that produces can cause the characteristic of storage medium to change, and become inequality etc. as the refractive index of clear zone and dark space, and this characteristic depends on the local strength of interference figure.By under the condition identical, shine the reproduction that the material that writes down can obtain institute's recorded hologram with reference beam, promptly to recorded reproduction with recording process.This mode that information is carried out page formula storage in the mode of holograph makes full use of the concurrency of optics.The advantage that holographic optical storage relies on highly redundant degree, high storage capacity, high data rate and short access time, lower information bit price, other storage meanss such as content addressed that can walk abreast can not be substituted, so caused extensive concern.
The core of light holographic storage technology is a storage medium, and storage medium is divided into erasable and one-time write two classes substantially.The one-time write storage medium has a variety of, and wherein photopolymer has advantages such as highly sensitive, that memory capacity is high, the information holding time is long, and extensive studies is arranged.Photopolymer generally partly is made up of monomer, light trigger, photosensitizer, matrix etc.Under the irradiation of interference light, thereby form refractive-index grating by the polymerization and of the diffusion of dark place monomer of bright place monomer in the matrix to bright place, and recorded information.Can produce volumetric contraction but one of shortcoming of photopolymer is a material when reacting, volumetric contraction will cause the Bragg angle mismatch, thereby influence the quality of recorded information.And because the manufacture craft restriction of current material, material thickness is difficult to increase, and information storage capacity is restricted.
Data can be deleted and write to erasable storage medium repeatedly, repeatedly uses, and it is divided into inorganic material and organic material two big classes.Inorganic material is representative with the lithium columbate crystal.But the lithium niobate production cost is very high, and shape is subjected to the crystalline size restriction, and the data that write etc. need be carried out post-processed ability long preservation such as heat fixation, have influenced practicality.It is representative that organic material is sold off compound with the light that contains azobenzene group.Azobenzene group can produce anti-(trans-)-suitable (cis-) photoisomerization under the specific wavelength optical excitation.When linearly polarized light acts on anisotropic azobenzene group, the light isomery circulation of trans-cis-trans can take place in molecule, linearly polarized light excites those transistion moments molecule parallel with the polarization direction selectively, after the circulation through repeatedly trans-cis-trans, molecule trends towards vertical signal polarisation of light direction and arranges, change has taken place in final molecular orientation, has produced photorefractive effect.It is not subjected to the light-struck azobenzene group of signal and have refractive index difference, and then write down data.On the contrary, can wipe the light signal of having stored with nonpolarized light or circularly polarized light irradiation sample.But azobenzene compound has limited its application in light holographic memory field owing to have that destructiveness is read, canned data is easily lost and problem such as refractive index modulation degree is low.
Summary of the invention
The objective of the invention is to solve common erasable type light and sell off the deficiency that holographic storage material exists, the azobenzol liquid crystal holography storage material that provide a kind of and can not take place that destructiveness is read, canned data is difficult for losing, memory capacity is big.
Another object of the present invention is to provide a kind of simple to operate, with low cost and at room temperature can prepare the preparation method of the azobenzol liquid crystal holography storage material of difformity thickness.
To achieve these goals, the present invention adopts following technical scheme:
A kind of azobenzol liquid crystal holography storage material comprises silicon dioxide, contains the azobenzene group compound and contains the liquid crystal group compound.Wherein, silicon dioxide is as host material, and how many its consumptions need not special qualification, and those skilled in the art can adjust in proper range.Azobenzene compound is sold off material as light, and the liquid crystal group is sold off enhancing substance as light.The mol ratio of azobenzene group and liquid crystal group is 0.5～10 in the material: between 1.
The preparation method of above-mentioned azobenzol liquid crystal holography storage material, comprise the steps: earlier the sol precursor hydrolysis, adding contains the azobenzene group compound and contains the liquid crystal group compound in the colloidal sol that obtains then, leaves standstill gel in room temperature after mixing and then solidifies.What preparation method of the present invention adopted is sol-gel process, can carry out in the mode of gentleness reaction at ambient temperature, and because the consistance of solidifying can make functional group be evenly dispersed in the matrix, so the increase of thickness can't influence the optical property of material.This material is in light holographic recording process, because the support of rigidity silica matrix, suitable-transconfiguration azobenzene group can be taken place change the surface relief grating that is produced and be controlled in the suitable scope.
Silica matrix forms by sol precursor generation hydrolysis-gel-curing reaction.Described sol precursor is the silane compound that contains two or more methoxy or ethoxies, is preferably ethyl orthosilicate, gamma-aminopropyl-triethoxy-silane, γ-glycidyl ether oxygen propyl trimethoxy silicane, γ-methacryloxypropyl trimethoxy silane or gamma-mercaptopropyltriethoxysilane.
There is azobenzene group in containing in the azobenzene group compound in the matrix, and this azobenzene group is azobenzene (each functional group that is connected and forms with a phenyl ring of two singly-bounds N=N-).Described azobenzene group compound can be micromolecular compound, high molecular polymer, hyperbranched compound, dendrimer etc.It can be to be dispersed in the matrix with physical admixture; Also can be by with matrix in side chain generation chemical reaction, be dispersed in the matrix in the mode of grafting.Preferred azobenzene compound be to butoxy azobenzene, 4-methoxyl-4 '-butyl azobenzene, 4,4 '-two (4-hydroxyazobenzene) biphenyl, to nitro-azo phenol etc.
The liquid crystal group compound that contains in the matrix can be to be dispersed in the matrix with physical admixture; Also can be by with matrix in side chain generation chemical reaction, be dispersed in the matrix in the mode of grafting.Be not limited only to contain a kind of liquid crystal group in the matrix, also can contain two kinds and two kinds of different liquid crystal groups simultaneously.The described liquid crystal group compound that contains is that azomethine is that liquid crystal, benzoic ether are that liquid crystal, biphenyl are, terphenyl is that liquid crystal, cyclohexylpentanoic acid phenyl ester are one or more potpourris in liquid crystal, phenylcyclohexane system or the xenyl hexamethylene methane series liquid crystal.
Azobenzol liquid crystal holography storage material of the present invention contains azobenzene and the liquid crystal group and the low refractive index silica matrix of high index of refraction.Under light action, azobenzene functional group can take place photic trans → cis and cis → trans-isomerism and thermic cis → trans-isomerism circulation.Because azobenzene group absorbs the selectivity of polarized light, the azobenzene compound of original mixed and disorderly random arrangement finally tends to finish orientation on the direction perpendicular to the pumping light electric vector, produces photorefractive effect.The azobenzene group of cis is and turns the shape structure, and the diameter of axle is smaller, can not be as mesomorphic unit.Trans azobenzene group be have larger axis directly than club shaped structure, can be used as mesomorphic unit, the characteristic of liquid crystal group is arranged, therefore will influence the arrangement of non-azobenzene liquid crystal group on every side.Because have very strong intermolecular interaction between trans azobenzene and liquid crystal group, the liquid crystal group forms identical orientation with azobenzene group at last by continuous twist alignment.There is birefringence effect in the liquid crystal group, will strengthen already present azobenzene group photorefractive effect, increases the refractive index modulation degree of material, and then increases the memory capacity of material.Because after the orientation of liquid crystal group generation rule, it is more regular tight that its arrangement will become, and be not vulnerable to the influence of heat fortune merit and impurity light, so the data preservation will become lasting.If desired during obliterated data,, upset azobenzene and the regularly arranged of liquid crystal group gets final product with nonpolarized light or circularly polarized light irradiation material.This azobenzol liquid crystal holography storage material can be stored multiple image on same point.During with the irradiation of nonpolarized light or circularly polarized light, erasable data then.Recorded information is repetitive erasing and writing in a manner described, repeatedly uses.
Compared with prior art, the present invention has following beneficial effect:
1. the host material that azobenzol liquid crystal holography storage material of the present invention uses is silicon dioxide structure, has good optical characteristic (high printing opacity and low scattered power).The refractive index of matrix is lower, sells off the compound coupling with the light that high index is arranged and can obtain high refractive index modulation degree.
2. the existence of liquid crystal group can be strengthened the azobenzene group chance photorefractive effect that light produced, and improves the diffraction efficiency of material, and then has increased information storage capacity; The regularly arranged influence that can not be subjected to thermal motion and non-flashlight of liquid crystal group, time data memory prolongs greatly.
Since the cis-trans-isomer of azobenzene group can be under the irradiation of flashlight the phase co-conversion, and induce the arrangement of liquid crystal group, so data can repetitive erasing and write.
4. the preparation method is simple, and it is promptly curable that the colloidal sol that will contain azobenzene and liquid crystal group is placed a couple of days in room temperature, and material shape can be selected suitable mould as required.
Description of drawings
Fig. 1 a is the material memory image experiment test figure as a result of embodiment 1.
Fig. 1 b is the material memory image experiment test figure as a result of embodiment 1.
Fig. 1 c is the material memory image experiment test figure as a result of embodiment 1.
Fig. 2 a is the material memory image experiment test figure as a result of embodiment 1.
Fig. 2 b is the material memory image experiment test figure as a result of embodiment 1.
Fig. 2 c is the material memory image experiment test figure as a result of embodiment 1.
Fig. 3 is the photic isomate process of azobenzene group.
Fig. 4 ordered state synoptic diagram of molecular cell in the material when not storing data.
The ordered state synoptic diagram of molecular cell in material during Fig. 5 interference light record data.
The ordered state synoptic diagram of molecular cell in the material after Fig. 6 data recording finishes.
Embodiment
Embodiment 1:
1. azo-benzene units is synthetic
(7.8g 0.05mol) adds in the solution of 17ml (0.2mol) concentrated hydrochloric acid and 10ml water, stirs and mixes to butoxy aniline.With the oil bath heating, it is limpid that solution becomes is got, and puts into the cryosel bath then rapidly and stir to obtain good crystal.Maintain the temperature at 0-5 ℃, (3.5g is 0.05mol) with 20ml water and stirring dropwise to drip sodium nitrite.Behind the 30min, the urea that adds equivalent is with the remaining sodium nitrite that neutralizes, and reaction process obtains diazonium salt solution by the monitoring of starch-kalium iodide test paper.(4.9g, (4g, 0.05mol) aqueous solution are cooled to mixed liquor below 10 ℃ phenol in ice bath, add 20g ice then 0.05mol) to be dissolved in 10% NaOH.Above-mentioned diazonium salt solution is slowly splashed into, and stir 1h fast, add saturated sodium acetate solution adjusting pH value then and be 6-7.Temperature keeps 3h at 0-10 ℃, and the potpourri that obtains filters and cleans with a large amount of distilled water, and vacuum drying at room temperature then obtains compound 1.
Compound 1 (13.5g, 0.05mol), the 1-n-butyl bromide (6.9g, 0.05mol), sal tartari (13.8g, 0.1mol) add among the DMF of 80ml, in 80 ℃ of reaction 20h, solution is poured in the 250ml water then, there is sediment to separate out, filters, clean and drying with a large amount of distilled water.The gained crude product is an eluant, eluent with chloroform/normal hexane, separates on silicagel column, obtains compound 2.
2. liquid crystal cells is synthetic
'-biphenyl diphenol (9.3g, 0.05mol) and sal tartari (13.8g 0.1mol) adds among the DMF of 100ml, adding 1-n-butyl bromide behind the stirring 1h (6.9g, 0.05mol), above-mentioned mixed liquor is in 80 ℃ of reaction 20h, then solution is poured in the 250ml water, filtered, clean and drying with a large amount of distilled water.The gained crude product is an eluant, eluent with chloroform/normal hexane, separates on silicagel column, obtains compound 3.
3. the preparation of light holographic material
To γ-glycidyl ether oxygen propyl trimethoxy silicane (9.4g, 0.04mol) and ethyl orthosilicate (2g adds 2.8ml water in 0.01mol), and to regulate pH with hydrochloric acid be about 3.Solution obtains limpid colloidal sol behind stirring at room 3h, (3.3g, 0.01mol) (6g 0.02mol), stirs 1h with compound 3 to add compound 2 then.This colloidal sol is poured in the mould after filtering with 0.45 μ m teflon filter, and room temperature is placed after 3 days and promptly got the light holographic storage material.The related compound synthetic route is as follows:
4. material properties test
The experiment light path:
Adopt ± 45 ° of polarization combination pumping configurations.Pump light Ar
+Laser (514.5nm) is as writing light inlet, be divided into two bundle aplanatic light beams (being respectively information carrying beam and reference beam) through beam splitter, through being incident on the same area formation holographic grating on the sample surfaces with an adjustable-angle θ intersection behind the catoptron and the polarizer.The equivalent optical path of information light and reference light, light intensity is all 200mW/cm
2, again by to regulate light field direction of vibration that the polarizer makes two bunch polarizations write light inlet be orthogonal and become with plane of incidence normal ± 45 °.Surveying light He-Ne laser (632.8nm) is modulated to circularly polarized light by catoptron and the polarizer and λ/4 wave plates and impinges perpendicularly on the zone that has optical grating construction in the sample.Survey light by behind the sample, produce diffraction, with the Ar of narrow band pass filter elimination by sample
+Laser (comprising transmitted light and scattered light) by the single order diffraction light power that connects digital oscillographic photodetector observation He-Ne light rule over time, obtains the time dependent situation of optical grating construction in the sample.
The performance test results:
The diffraction efficiency of material reaches 2.1%, even diffraction efficiency still has 2.0% after placing fortnight.The largest refractive index degree of modulation Δ n=0.023 of material, luminous sensitivity is 6.3 * 10
-3Cm
2/ J.The result is as follows for material memory image experiment test, and Fig. 1 a, 1b, 1c are three width of cloth images in the storage of holographic storage material the same area.After wiping above-mentioned image, other three width of cloth images (Fig. 2 a, Fig. 2 b, Fig. 2 c) have been stored at the same area again with the circular polarization irradiation.Realized the purpose of the erasable storage data of material, and after material placed for 4 week, image information was without any losing.
The azobenzol liquid crystal holography storage material of embodiment 1 is made up of azobenzene compound, liquid-crystal compounds and silica matrix.Azobenzene group has two kinds of isomeride of trans/cis (Fig. 3).Because azobenzene group absorbs the selectivity of polarized light, the azobenzene compound (Fig. 4) of original mixed and disorderly random arrangement is finished orientation (Fig. 5) on the direction perpendicular to the pumping light electric vector.By strong intermolecular interaction between trans azobenzene and liquid crystal group, the continuous twist alignment of liquid-crystal compounds forms identical orientation with azobenzene group at last, as shown in Figure 6.But this material can be stored multiple image and repetitive erasing and write on same point, repeatedly uses.
Embodiment 2:
1. contain the synthetic of azobenzene and liquid crystal group compound
Adding 4-cyano group-4 in the 100ml methylene chloride '-carboxyl biphenyl (8.3g; 0.037mmol), 4; 4 '-dihydroxy azobenzene (2.6g; 0.012mmol) and 4-dimethylamino naphthyridine (4.5g; 0.037mmol); mix the logical nitrogen in back as blanket gas, add 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDCHCl) then.Potpourri adds the methylene chloride dilution behind stirring at room 12h, use saturated NH more respectively
4Cl aqueous solution and saturated sodium-chloride water solution clean.Organic layer obtains compound 4 with anhydrous sodium sulfate drying, solvent evaporated with the silica gel chromatographic column purification.
2. the preparation of light holographic material
To γ-glycidyl ether oxygen propyl trimethoxy silicane (9.4g, 0.04mol) and ethyl orthosilicate (2g adds 2.8ml water in 0.01mol), and to regulate pH with hydrochloric acid be about 3.Solution obtains limpid colloidal sol behind stirring at room 3h, (6.2g 0.01mol), stirs 1h to add compound 4 then.This colloidal sol is poured in the mould after filtering with 0.45 μ m teflon filter, and room temperature is placed after 3 days and promptly got the light holographic storage material.The related compound synthetic route is as follows:
4. material properties test
The experiment light path is identical with embodiment 1.The diffraction efficiency of material is 1.2%.The largest refractive index degree of modulation Δ n=0.011 of material, luminous sensitivity is 4.2 * 10
-3Cm
2/ J.
Embodiment 3:
1. azo-benzene units is synthetic
(6.2g 0.05mmol) adds in the solution of 17ml concentrated hydrochloric acid (0.2mol) and 10ml water P-nethoxyaniline, stirs to mix.With the oil bath heating, it is limpid that solution becomes is got, and puts into cryosel then rapidly and bathe stirring to obtain good crystal.Maintain the temperature at 0-5 ℃, (3.5g is 0.05mol) with 20mol water and stirring dropwise to drip sodium nitrite.Behind the 30min, with remaining sodium nitrite, reaction process obtains diazonium salt solution by the monitoring of starch-kalium iodide test paper in the urea of adding equivalent.(4.9g, (4g, 0.05mol) aqueous solution are cooled to mixed liquor below 10 ℃ with ice bath phenol, add 20g ice then 0.05mol) to be dissolved in 10% NaOH.Above-mentioned diazonium salt solution is slowly splashed into, stir 1h fast, add saturated sodium acetate solution adjusting pH value then and be 6-7.Maintain the temperature at 3h between 0-10 ℃, the potpourri that obtains filters and cleans with a large amount of distilled water, and vacuum drying at room temperature then obtains compound 5.
With compound 5 (9.13g, 0.04mmol) and allyl bromide, bromoallylene (7.3g 0.06mmol) joins in the dry DMF of 150ml, adds sal tartari (13.8g, 0.1mmol), cool to room temperature behind 60 ℃ of reaction 20h adds the distilled water of 300ml then, filtering mixt and with the vacuum drying of gained solid, obtain crude product, crude product is an eluant, eluent with the chloroform, separates on silicagel column, obtains compound 6.
2. liquid crystal cells is synthetic
(75g 0.40mol), stirs fast down to add '-biphenyl diphenol in the aqueous solution of 10% NaOH of 400ml in ice-water bath.(50g 0.40mol) slowly splashes in the time of 1h in the solution dimethyl suflfate, stirs fast.After dropwising, filter and to obtain sediment and be dissolved in again in 10% the sodium hydroxide solution of 400ml.Solution is heated to boiling back cool to room temperature, filters then.The solid matter that obtains adds in the water of 2000ml, is heated to boiling, filters then, and gained filtrate is heated to 70 ℃, adds 20% concentrated hydrochloric acid regulator solution then and becomes acidity.Gained solution is put the static white crystal that obtains, and with ethyl alcohol recrystallization 2 times, obtains compound 7.Productive rate 30%.
With compound 7 (4g, 0.02mmol) and allyl bromide, bromoallylene (3.6g, 0.03mmol) be added in the dry DMF of 100ml, add again sal tartari (13.8g, 0.1mmol), in 60 ℃ the reaction 20h after cool to room temperature, the distilled water that adds 200ml, filtering mixt and with the vacuum drying of gained solid is crossed the silica gel liquid-phase chromatographic column, obtains compound 8.
3. the preparation of light holographic material
Compound 6 (2.7g, 0.01mmol) and compound 8 (7.2g, 0.03mmol) be dissolved in the toluene of 100ml, add the 0.5g azoisobutyronitrile, mix the back and add gamma-mercaptopropyltriethoxysilane (9.5g, 0.04mmol), in 60 ℃ of reaction 10h, the back that finishes feeds a large amount of nitrogen and dries up toluene solvant.In this potpourri, add ethyl orthosilicate (2g, 0.01mol) and water (2.8g 0.16mol), is about 3 with hydrochloric acid conditioning solution pH, and 50 ℃ were stirred 5 hours down, obtain containing the colloidal sol of azobenzene and liquid crystal group.This colloidal sol is poured in the mould after filtering with 0.45 μ m teflon filter, and room temperature is placed after 3 days and promptly got the light holographic storage material.The related compound synthetic route is as follows:
4. material properties test
The experiment light path is identical with embodiment 1.The diffraction efficiency of material is 2.6%.The largest refractive index degree of modulation Δ n=0.030 of material, luminous sensitivity is 4.9 * 10
-3Cm
2/ J.
Claims (3)
1. an azobenzol liquid crystal holography storage material is characterized in that comprising silicon dioxide, contains the azobenzene group compound and contains the liquid crystal group compound, and the mol ratio of azobenzene group and liquid crystal group is 0.5～10: 1; Described contain the azobenzene group compound for to butoxy azobenzene, 4-methoxyl-4 '-butyl azobenzene, 4,4 '-two (4-hydroxyazobenzene) biphenyl or to nitro-azo phenol; The described liquid crystal group compound that contains is that azomethine is that liquid crystal, benzoic ether are that liquid crystal, biphenyl are that liquid crystal, terphenyl are that liquid crystal, cyclohexylenedinitrilotetraacetic acid phenyl ester are one or more potpourris in liquid crystal, cyclohexylbenzene system or the xenyl hexamethylene methane series liquid crystal.
2. the preparation method of the described azobenzol liquid crystal holography storage material of claim 1, it is characterized in that comprising the steps: earlier with the sol precursor hydrolysis, adding contains the azobenzene group compound and contains the liquid crystal group compound in the colloidal sol that obtains then, leaves standstill gel in room temperature after mixing and then solidifies; Described sol precursor is the silane compound that contains two or more methoxy or ethoxies.
3. preparation method as claimed in claim 2 is characterized in that the described silane compound that contains two or more methoxy or ethoxies is one or more potpourris in ethyl orthosilicate, gamma-aminopropyl-triethoxy-silane, γ-glycidyl ether oxygen propyl trimethoxy silicane, γ-methacryloxypropyl trimethoxy silane or the gamma-mercaptopropyltriethoxysilane.
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| CN102809825B (en) * | 2012-07-26 | 2014-12-24 | 上海交通大学 | Holographic-grating-based three-dimensional display |
| CN104496844B (en) * | 2014-11-25 | 2017-01-04 | 江南大学 | A kind of preparation method of the alkyl photosensitive foam controller of oxygen diphenyl diimide |
| CN108456281A (en) * | 2018-01-16 | 2018-08-28 | 浙江大学 | Ferrocenyl azobenzene photoelectricity double-bang firecracker emergencing copolymer material and preparation method thereof for information storage |
| CN110339827A (en) * | 2019-06-27 | 2019-10-18 | 延边大学 | A photosensitive chromatographic stationary phase based on azobenzene photosensitive compound modified silicon base |
| CN111333023B (en) * | 2020-03-02 | 2023-09-26 | 北京大学 | Preparation method and application of solvent-induced photoresponsive polymer surface micro-nano structure |
| CN118259511A (en) * | 2022-12-20 | 2024-06-28 | 中兴通讯股份有限公司 | Holographic metamaterial negative film, preparation system and method of holographic metamaterial optical device |
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