CN109400505A - A kind of azobenzene isonitrile monomer and its polymer and preparation method - Google Patents
A kind of azobenzene isonitrile monomer and its polymer and preparation method Download PDFInfo
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Abstract
The invention discloses a kind of azobenzene isonitrile monomer and its polymer and preparation method, the wherein following general formula of the structure of azobenzene isonitrile polymer are as follows:In formula,Wherein, polymerization degree n=40~200, m 1,1.5,2,2.5 or 3.Preparation method includes that palladium chtalyst azobenzene isonitrile monomer polymerization prepares azobenzene isonitrile polymer.The present invention combines azobenzene with isonitrile, easy to operate, and synthesis is easy, and prepared polymer has very big potential using value in fields such as fluorescence probe, biological medicine, nanosecond science and technology, intellectual material, photoelectric materials.
Description
Technical field
The present invention relates to functional polymer and polymer reaction fields, and in particular to a kind of azobenzene isonitrile monomer and its poly-
Close object and preparation method.
Background technique
Poly- isonitrile (poly isocyanide) be find earliest have stablize one of macromolecule of helical conformation, property
Matter is stable, monomer is easy to get, polymerization is simple, in the solution with helical structure can be kept when solid-state well, thus be one
Plant significantly artificial-synthetic copolymer.Poly- isonitrile be first be reported have and stablize the polymer of helical conformation,
It, will when various functional groups (such as stimulating responsive group, photoswitch structure) are grafted in the side group of helix poly isonitrile
Assign this material new property and function, so that the functional polymer material of new construction, new capability is generated, in chiral molecules
There are important research significance and application in the fields such as identification, asymmetry catalysis and Chiral Separation, pharmaceutical carrier, liquid crystal display
Prospect.
In recent years, azobenzene derivatives not only have been used to synthesize intelligent polymerization as the function element that photoswitch responds
Object, liquid crystal material, molecular switch and molecule machine etc., and just promptly penetrating into chemical biology architectural study and analysis
Various aspects.
If azo molecules unit is grafted in the side group of helix poly isonitrile, the spiral high score of new construction will be generated
Son, and assign this material new structure and function, such as pharmaceutical indications, fluorescence probe, biosensor.Therefore, this field
Technical staff be dedicated to developing that a kind of property is stable, synthesis is easy and in fluorescence probe, biomedicine, nanosecond science and technology, intelligence
The fields such as material, photoelectric material have the azobenzene isonitrile polymer of potential value.
Summary of the invention
The purpose of the present invention is to provide a kind of azobenzene isonitrile monomer and its polymer and preparation methods, first by straight
It is bonded into method or ester-interchange method obtains azobenzene isonitrile monomer, be then catalyzed its polymerization using palladium catalyst and obtain azobenzene isonitrile
Polymer.The polymer by azobenzene in conjunction with isonitrile, it is easy to operate, synthesis be easy, and in fluorescence probe, biomedicine, receive
There is very big potential value in the fields such as rice science and technology, intellectual material, photoelectric material.
To achieve the above object, the invention provides the following technical scheme:
A kind of azobenzene isonitrile monomer, the general formula of the chemical structure of the monomer are as follows:
In formula
Wherein m is 1,1.5,2,2.5 or 3.
A kind of azobenzene isonitrile polymer, the general formula of the chemical structure of the polymer are as follows:
In formula
Wherein, polymerization degree n=40~200, m 1,1.5,2,2.5 or 3.
Preferably, the preparation method of a kind of azobenzene isonitrile monomer, comprising the following steps:
(1) 4- (phenyl phenodiazine base) phenol, reagent B, potassium iodide and potassium carbonate is weighed in reaction flask, to vacuumize, be filled with
Nitrogen；Under nitrogen atmosphere, solvent DMF is injected, reaction flask is placed in oil bath pan, after 80 DEG C are stirred 24 hours, elutriation is added
Yellow solid out filters drying, obtains product a；
(2) step (1) product a, reagent C, EDCI and DMAP are weighed to be put into two mouth flask, DCM is added as solvent,
After reaction 5 hours, after concentration, is purified with chromatographic column, obtain product b；
(3) step (2) product b and zinc powder are weighed in two mouth flask, vacuumizes, is filled with nitrogen, under nitrogen atmosphere, note
Enter ethyl alcohol and glacial acetic acid and anhydrous sodium bicarbonate quenching reaction is added after reaction 24 hours, filter, concentration obtains product c；
(4) step (3) product c is weighed, vacuumizes, is filled with nitrogen, under nitrogen atmosphere, solvent EA is injected, is beaten at 0 DEG C
After entering formic anhydride, room temperature reaction 4h is then moved to, anhydrous sodium bicarbonate is added and removes extra acid, it is dry, it filters, concentration obtains
Product d；
(5) step (4) product d is weighed, vacuumizes, is filled with nitrogen, under nitrogen atmosphere, injects solvent DCM and triethylamine,
The BTC dissolved with DCM is added dropwise at 0 DEG C, reacts 1h, after concentration, is purified with chromatographic column, obtain the azobenzene isonitrile
Monomer.
The synthetic route of the azobenzene isonitrile monomer is as follows:
Preferably, the reagent C is one of o-nitrobenzoic acid, m-Nitrobenzoic Acid, paranitrobenzoic acid or several
Kind.
Preferably, the preparation method of a kind of azobenzene isonitrile monomer, comprising the following steps:
(1) 4- (phenyl phenodiazine base) phenol, reagent B, potassium iodide and potassium carbonate is weighed in reaction flask, to vacuumize, be filled with
Nitrogen injects solvent DMF, reaction flask is placed in oil bath pan under nitrogen atmosphere, and after 80 DEG C are stirred 24 hours, elutriation is added
Yellow solid out filters drying, obtains product；
(2) step (1) product, Pentafluorophenol isonitrile monomer and DMAP are weighed in reaction flask, vacuumizes, is filled with nitrogen,
Under the atmosphere of nitrogen, dry triethylamine and THF are injected, reaction flask is placed in after stirring 4~5h at room temperature, is filtered, concentration
It is purified afterwards with chromatographic column, obtains azobenzene isonitrile monomer.
The synthetic route of the azobenzene isonitrile monomer is as follows:
Preferably, the reagent B be ethylene chlorhydrin, ethylene bromohyrin, trimethylene chlorohydrin, the bromo- 1- propyl alcohol of 3-, 1- methaform,
One or more of the chloro- 1- amylalcohol of the bromo- n-butyl alcohol of 4-, 5-, the bromo- 1- amylalcohol of 5-, the chloro- 1- hexanol of 6-, the bromo- 1- hexanol of 6-.
Preferably, the preparation method of a kind of azobenzene isonitrile polymer, comprising the following steps:
Palladium catalyst and azobenzene isonitrile monomer are added in polymerization bottle, under the conditions of anhydrous and oxygen-free, vacuum nitrogen gas,
Dry solvent A is added, in 50~90 DEG C of back flow reactions 6~for 24 hours, methanol is added and terminates reaction, products therefrom is washed with methanol
After washing, it is dried under vacuum to mass conservation, obtains azobenzene isonitrile polymer P, wherein the general structure of palladium catalyst are as follows:
In formula,
The general structure of P are as follows:
In formula,
Wherein polymerization degree n=40~200, m 1,1.5,2,2.5 or 3.
Preferably, the molar ratio of the palladium catalyst and the different nitrile monomer of benzene is 1:(40~200), when azobenzene isonitrile
Monomer input amount is 30~100mg, and the additional amount of solvent A is 1~3mL.
Preferably, the preparation method of a kind of azobenzene isonitrile polymer, comprising the following steps:
Palladium catalyst and azobenzene isonitrile monomer are added in polymerization bottle, under the conditions of anhydrous and oxygen-free, vacuum nitrogen gas,
Dry solvent A is added, in 55~60 DEG C of back flow reactions 20~for 24 hours, methanol is added and terminates reaction, products therefrom is washed with methanol
After washing, it is dried under vacuum to mass conservation, obtains azobenzene isonitrile polymer P, the general structure of P is as follows:
In formula
Wherein polymerization degree n=40~200, m 1,1.5,2,2.5 or 3.
Preferably, the preparation method of a kind of azobenzene isonitrile polymer, the solvent A are tetrahydrofuran, trichlorine
One or more of methane, toluene.
Compared with prior art, the beneficial effects of the present invention are:
(1) the azobenzene isonitrile Macroscopic single crystal in the present invention is simple, not harsh to experiment condition requirement, easy to operate,
Reaction easily carries out.
(2) synthesis step can simplify by the transesterification of Pentafluorophenol isonitrile monomer, simple and quick can obtains azo
Benzene isonitrile monomer.
(3) the azobenzene isonitrile polymer in the present invention, raw material sources are extensive；For being catalyzed azobenzene isonitrile monomer reaction
Catalyst type it is more.
(4) the azobenzene isonitrile polymer in the present invention combines azobenzene with isonitrile, in fluorescence probe, biology doctor
There is very big application value in the fields such as, nanosecond science and technology, intellectual material, photoelectric material.
Detailed description of the invention
Fig. 1 is the nucleus magnetic hydrogen spectrum figure of azobenzene isonitrile monomer 3 in the embodiment of the present invention 3.
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of TPE base palladium catalyst in the embodiment of the present invention 5.
Fig. 3 is the nucleus magnetic hydrogen spectrum figure of propilolic alcohol palladium catalyst in the embodiment of the present invention 6.
Fig. 4 is the nucleus magnetic hydrogen spectrum figure of azobenzene isonitrile polymer P 1 in the embodiment of the present invention 4.
Fig. 5 is the gel permeation chromatogram of azobenzene isonitrile polymer P 1 in the embodiment of the present invention 4.
Fig. 6 be in the embodiment of the present invention 4 azobenzene isonitrile polymer P 1 in different proportion THF/H2It is glimmering in O mixed solution
Spectrogram, in fluorogram, H2The volume ratio of O and THF is followed successively by 60% from top to bottom, 50%, 40%, 30%, 20%,
10%, 0.
Specific embodiment
The technical scheme in the embodiments of the invention will be clearly and completely described below, it is clear that described implementation
Example is only a part of the embodiments of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is general
Logical technical staff every other embodiment obtained without making creative work belongs to what the present invention protected
Range.
Embodiment 1
The synthetic method of azobenzene isonitrile monomer 1 is as follows:
2g 4- (phenyl phenodiazine base) phenol, 1.83g ethylene bromohyrin, 1.94g potassium iodide and 2.05g potassium carbonate is weighed in anti-
It answers in bottle, vacuumizes, be filled with nitrogen；Under nitrogen atmosphere, 80mL DMF is injected, reaction flask is placed in oil bath pan, 80 DEG C are stirred
After mixing for 24 hours, a large amount of elutriations are added and go out yellow solid, filters drying, obtains product 1, wherein the structural formula of product 1 are as follows:
The route of the present embodiment synthetic product 1 is as follows:
500mg product 1,500mg Pentafluorophenol isonitrile monomer and 390mg DMAP are weighed in reaction flask, vacuumizes, fills
Enter nitrogen；Under the atmosphere of nitrogen, dry triethylamine and THF are injected；Reaction is placed in after stirring 5 hours at room temperature, filtering,
It after concentration, is purified with chromatographic column, obtains azobenzene isonitrile monomer 1, wherein the structural formula of azobenzene isonitrile monomer 1 are as follows:
The route that the present embodiment synthesizes azobenzene isonitrile monomer 1 is as follows:
Embodiment 2
The synthetic method of azobenzene isonitrile monomer 2 is as follows:
2g 4- (phenyl phenodiazine base) phenol, 1.59g 1- methaform, 1.95g potassium iodide and 2.03g potassium carbonate are weighed in anti-
It answers in bottle, vacuumizes, be filled with nitrogen；Under nitrogen atmosphere, 80mL DMF is injected, reaction flask is placed in oil bath pan, 80 DEG C are stirred
After mixing for 24 hours, a large amount of elutriations are added and go out yellow solid, filters drying, obtains product 2, wherein the structural formula of product 2 are as follows:
The route of the present embodiment synthetic product 2 is as follows:
500mg product 2,500mg Pentafluorophenol isonitrile monomer and 390mg DMAP are weighed in reaction flask, vacuumizes, fills
Enter nitrogen；Under the atmosphere of nitrogen, dry triethylamine and THF are injected；Reaction is placed in after stirring 5 hours at room temperature, filtering,
It after concentration, is purified with chromatographic column, obtains azobenzene isonitrile monomer 2, wherein the structural formula of azobenzene isonitrile monomer 2 are as follows:
The route that the present embodiment synthesizes azobenzene isonitrile monomer 2 is as follows:
Embodiment 3
The synthetic method of azobenzene isonitrile monomer 3 is as follows:
Weigh 4g 4- (phenyl phenodiazine base) phenol, the chloro- 1- hexanol of 4.1g 6-, 3.88g potassium iodide and 4.15g potassium carbonate in
It in reaction flask, vacuumizes, is filled with nitrogen；Under nitrogen atmosphere, 100mL DMF is injected, reaction flask is placed in oil bath pan, 80 DEG C
After stirrings for 24 hours, a large amount of elutriations are added and go out yellow solid, filters drying, obtains product 3, wherein the structural formula of product 3 are as follows:
The route of the present embodiment synthetic product 3 is as follows:
500mg product 3,500mg Pentafluorophenol isonitrile monomer and 390mg DMAP are weighed in reaction flask, vacuumizes, fills
Enter nitrogen；Under the atmosphere of nitrogen, dry triethylamine and THF are injected；Reaction is placed in after stirring 5 hours at room temperature, filtering,
It after concentration, is purified with chromatographic column, obtains azobenzene isonitrile 3, wherein the structural formula of azobenzene isonitrile monomer 3 are as follows:
The route that the present embodiment synthesizes azobenzene isonitrile monomer 3 is as follows:
The nucleus magnetic hydrogen spectrum figure of azobenzene isonitrile monomer 3 is as shown in Figure 1.
Embodiment 4
Azobenzene isonitrile polymer P 1 the preparation method is as follows:
6.75mg methoxyl group palladium catalyst and 198.46mg azobenzene isonitrile monomer 3 are added in polymerization bottle, in anhydrous nothing
Under the conditions of oxygen, the dry tetrahydrofuran of 2mL is added in vacuum nitrogen gas, in 55 DEG C of reaction 12h, methanol is added and terminates reaction, will
After products therefrom is washed with methanol, it is dried under vacuum to mass conservation, obtains azobenzene isonitrile polymer P 1.
The route that the present embodiment catalysis 3 polymerization of azobenzene isonitrile monomer prepares azobenzene isonitrile polymer P 1 is as follows:
Fig. 4 is the nucleus magnetic hydrogen spectrum figure of azobenzene isonitrile polymer P 1 in the present embodiment.
Fig. 5 is the gel permeation chromatogram of azobenzene isonitrile polymer P 1 in the present embodiment.
Fig. 6 be in the present embodiment azobenzene isonitrile polymer P 1 in different proportion THF/H2Fluorescence Spectra in O mixed solution
Figure, in the fluorogram of Fig. 6, H2The volume ratio of O and THF is followed successively by 60% from top to bottom, 50%, 40%, 30%, 20%,
10%, 0.
Embodiment 5
Azobenzene isonitrile polymer P 2 the preparation method is as follows:
4.8mg TPE base palladium catalyst is added in polymerization bottle (the nucleus magnetic hydrogen spectrum figure of TPE base palladium catalyst is as shown in Figure 2)
With 94mg azobenzene isonitrile monomer 3, under the conditions of anhydrous and oxygen-free, the dry tetrahydrofuran of 2mL is added in vacuum nitrogen gas,
55 DEG C of reaction 12h are added methanol and terminate reaction, after products therefrom is washed with methanol, are dried under vacuum to mass conservation, obtain idol
Pyridine isonitrile polymer P 2.
The route that the present embodiment catalysis 3 polymerization of azobenzene isonitrile monomer prepares azobenzene isonitrile polymer P 2 is as follows:
Embodiment 6
Azobenzene isonitrile polymer P 3 the preparation method is as follows:
3.9mg propilolic alcohol palladium catalyst (nucleus magnetic hydrogen spectrum figure such as Fig. 3 institute of propilolic alcohol palladium catalyst is added in polymerization bottle
Show) and 134.48mg azobenzene isonitrile monomer 3, under the conditions of anhydrous and oxygen-free, the dry chloroform of 2mL is added in vacuum nitrogen gas,
In 55 DEG C of reaction 12h, methanol is added and terminates reaction, after products therefrom is washed with methanol, is dried under vacuum to mass conservation, obtains
Azobenzene isonitrile polymer P 3.
The route that the present embodiment catalysis 3 polymerization of azobenzene isonitrile monomer prepares azobenzene isonitrile polymer P 3 is as follows:
Embodiment 7
The synthetic method of azobenzene isonitrile monomer 4 is as follows:
(1) 4g 4- (phenyl phenodiazine base) phenol, the chloro- 1- hexanol of 4.1g 6-, 3.88g potassium iodide and 4.15g carbonic acid are weighed
Potassium vacuumizes in reaction flask, is filled with nitrogen；Under nitrogen atmosphere, 100mL DMF is injected, reaction flask is placed in oil bath pan,
After 80 DEG C of stirrings for 24 hours, a large amount of elutriations are added and go out yellow solid, filters drying, obtains 5.5g product a；
(2) 2.8g paranitrobenzoic acid, 1.64g DMAP and 3.9g EDCI are weighed in two mouth flask, it is molten that DCM is added
Solution, stirs 10min on magnetic stirring apparatus；It weighs 5g step (1) product a to be added in above-mentioned solution, continues to be stirred to react 5 small
Shi Hou, it is concentrated, it is purified with chromatographic column, obtains 7g product b；
(3) 5g step (2) product b and 5.8g zinc powder is weighed in two mouth flask, to vacuumize, be filled with nitrogen；In nitrogen atmosphere
Under enclosing, injects ethanol in proper amount and glacial acetic acid (volume ratio 3:1) and anhydrous sodium bicarbonate quenching reaction is added after reaction 24 hours,
Filtering, concentration, obtains 4.5g product c；
(4) 4.5g step (3) product c is weighed, vacuumizes, is filled with nitrogen；Under nitrogen atmosphere, solvent EA is injected, at 0 DEG C
Under squeeze into 8mL formic anhydride after, then move to room temperature reaction 4h, anhydrous sodium bicarbonate be added and removes extra acid, it is dry, filter, it is dense
Contracting, obtains 4.5g product d；
(5) 3g step (4) product d is weighed, vacuumizes, is filled with nitrogen；Under nitrogen atmosphere, solvent DCM and three second are injected
The BTC that 1.76g has been dissolved with DCM is added dropwise in amine at 0 DEG C, reacts 1h, after concentration, is purified with chromatographic column, obtains 2.5g idol
Pyridine isonitrile.
The route that the present embodiment synthesizes azobenzene isonitrile monomer 4 is as follows:
Above content is only to structure of the invention example and explanation, affiliated those skilled in the art couple
Described specific embodiment does various modifications or additions or is substituted in a similar manner, without departing from the present invention
Structure or beyond the scope defined by this claim, be within the scope of protection of the invention.
Claims (10)
1. a kind of azobenzene isonitrile monomer, which is characterized in that the general formula of the chemical structure of the monomer is as follows:
In formula
Wherein m is 1,1.5,2,2.5 or 3.
2. a kind of azobenzene isonitrile polymer, which is characterized in that the general formula of the chemical structure of the polymer is as follows:
In formula
Wherein, polymerization degree n=40~200, m 1,1.5,2,2.5 or 3.
3. a kind of preparation method of azobenzene isonitrile monomer according to claim 1, which is characterized in that including following step
It is rapid:
(1) 4- (phenyl phenodiazine base) phenol, reagent B, potassium iodide and potassium carbonate is weighed in reaction flask, to vacuumize, be filled with nitrogen；
Under nitrogen atmosphere, solvent DMF is injected, reaction flask is placed in oil bath pan, after 80 DEG C are stirred 24 hours, elutriation is added and goes out yellow
Solid filters drying, obtains product a；
(2) step (1) product a, reagent C, EDCI and DMAP are weighed to be put into two mouth flask, DCM is added as solvent, reaction
It after 5 hours, after concentration, is purified with chromatographic column, obtains product b；
(3) step (2) product b and zinc powder are weighed in two mouth flask, vacuumizes, is filled with nitrogen, under nitrogen atmosphere, injects second
Anhydrous sodium bicarbonate quenching reaction is added after reaction 24 hours in pure and mild glacial acetic acid, filters, and concentration obtains product c；
(4) step (3) product c is weighed, vacuumizes, is filled with nitrogen, under nitrogen atmosphere, solvent EA is injected, squeezes into first at 0 DEG C
After acid anhydrides, room temperature reaction 4h is then moved to, anhydrous sodium bicarbonate is added and removes extra acid, it is dry, it filters, concentration obtains product
d；
(5) step (4) product d is weighed, vacuumizes, is filled with nitrogen, under nitrogen atmosphere, solvent DCM and triethylamine are injected, 0
The BTC dissolved with DCM is added dropwise at DEG C, reacts 1h, after concentration, is purified with chromatographic column, obtain the azobenzene isonitrile list
Body.
4. a kind of preparation method of azobenzene isonitrile monomer according to claim 3, it is characterised in that: the reagent C is
One or more of o-nitrobenzoic acid, m-Nitrobenzoic Acid, paranitrobenzoic acid.
5. a kind of preparation method of azobenzene isonitrile monomer according to claim 1, which is characterized in that including following step
It is rapid:
(1) 4- (phenyl phenodiazine base) phenol, reagent B, potassium iodide and potassium carbonate is weighed in reaction flask, to vacuumize, be filled with nitrogen,
Under nitrogen atmosphere, solvent DMF is injected, reaction flask is placed in oil bath pan, after 80 DEG C are stirred 24 hours, elutriation is added and goes out yellow
Solid filters drying, obtains product；
(2) step (1) product, Pentafluorophenol isonitrile monomer and DMAP are weighed in reaction flask, vacuumizes, is filled with nitrogen, in nitrogen
Under the atmosphere of gas, dry triethylamine and THF are injected, reaction flask is placed in after stirring 4~5h at room temperature, filtering is used after concentration
Chromatographic column purification, obtains azobenzene isonitrile monomer.
6. a kind of preparation method of azobenzene isonitrile monomer according to claim 3 or 5, it is characterised in that: the reagent B
For ethylene chlorhydrin, ethylene bromohyrin, trimethylene chlorohydrin, the bromo- 1- propyl alcohol of 3-, 1- methaform, the bromo- n-butyl alcohol of 4-, the chloro- 1- amylalcohol of 5-,
One or more of the bromo- 1- amylalcohol of 5-, the chloro- 1- hexanol of 6-, the bromo- 1- hexanol of 6-.
7. a kind of preparation method of azobenzene isonitrile polymer according to claim 2, which is characterized in that including following step
It is rapid:
Palladium catalyst and azobenzene isonitrile monomer are added in polymerization bottle, under the conditions of anhydrous and oxygen-free, vacuum nitrogen gas is added
Dry solvent A is added methanol and terminates reaction in 50~90 DEG C of back flow reactions 6~for 24 hours, after products therefrom is washed with methanol,
It is dried under vacuum to mass conservation, obtains azobenzene isonitrile polymer P, wherein the general structure of palladium catalyst are as follows:
In formula,
The general structure of P are as follows:
In formula,
Wherein polymerization degree n=40~200, m 1,1.5,2,2.5 or 3.
8. a kind of preparation method of azobenzene isonitrile polymer according to claim 7, it is characterised in that: the palladium is urged
Agent and the molar ratio of the different nitrile monomer of benzene are 1:(40~200), it is molten when azobenzene isonitrile monomer input amount is 30~100mg
The additional amount of agent A is 1~3mL.
9. a kind of preparation method of azobenzene isonitrile polymer according to claim 2, which is characterized in that including following step
It is rapid:
Palladium catalyst and azobenzene isonitrile monomer are added in polymerization bottle, under the conditions of anhydrous and oxygen-free, vacuum nitrogen gas is added
Dry solvent A is added methanol and terminates reaction, products therefrom is washed with methanol in 55~60 DEG C of back flow reactions 20~for 24 hours
Afterwards, it is dried under vacuum to mass conservation, obtains azobenzene isonitrile polymer P, the general structure of P is as follows:
In formula
Wherein polymerization degree n=40~200, m 1,1.5,2,2.5 or 3.
10. a kind of preparation method of azobenzene isonitrile polymer according to claim 7 or 8 or 9, it is characterised in that: institute
Stating solvent A is one or more of tetrahydrofuran, chloroform, toluene.
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| CN111471467A (en) * | 2020-05-14 | 2020-07-31 | 商丘师范学院 | Polymer type lyotropic liquid crystal material, preparation method thereof and application thereof in chiral drug resolution |
| CN112062901A (en) * | 2020-08-14 | 2020-12-11 | 合肥工业大学 | Spiral fluorescent isonitrile copolymer and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110841613A (en) * | 2019-10-31 | 2020-02-28 | 合肥工业大学 | Chiral separation multifunctional cellulose-based material and preparation method thereof |
| CN110841613B (en) * | 2019-10-31 | 2022-05-17 | 合肥工业大学 | Chiral separation multifunctional cellulose-based material and preparation method thereof |
| CN111196774A (en) * | 2020-02-15 | 2020-05-26 | 桂林理工大学 | Asymmetric azobenzene capable of solid-liquid conversion and preparation method thereof |
| CN111471467A (en) * | 2020-05-14 | 2020-07-31 | 商丘师范学院 | Polymer type lyotropic liquid crystal material, preparation method thereof and application thereof in chiral drug resolution |
| CN111471467B (en) * | 2020-05-14 | 2023-04-25 | 商丘师范学院 | Polymer type lyotropic liquid crystal material, preparation method thereof and application thereof in chiral drug resolution |
| CN112062901A (en) * | 2020-08-14 | 2020-12-11 | 合肥工业大学 | Spiral fluorescent isonitrile copolymer and preparation method thereof |
| CN112062901B (en) * | 2020-08-14 | 2023-03-21 | 合肥工业大学 | Spiral fluorescent isonitrile copolymer and preparation method thereof |
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