CN108485643A - Thin polymer film and preparation method thereof with changing color resulting from acid and aggregation-induced emission performance - Google Patents
Thin polymer film and preparation method thereof with changing color resulting from acid and aggregation-induced emission performance Download PDFInfo
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
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- C08J2333/14—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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Abstract
Thin polymer film and preparation method thereof of the present invention with changing color resulting from acid and aggregation-induced emission performance, by carrying out free radical solution polymerization by conventional ethylene monomer and with changing color resulting from acid and the vinyl monomer of aggregation-induced emission performance, the copolymer material with changing color resulting from acid and aggregation-induced emission performance is prepared, copolymer material is dissolved and thin polymer film is made by solvent volatilization, the thin polymer film not only has changing color resulting from acid performance and aggregation-induced emission performance, also good film forming characteristics；In addition, the preparation method of the thin polymer film, simple for process, manufacturing cost is relatively low.
Description
Technical field
The present invention relates to technical field of organic luminescence materials, and in particular to one kind having changing color resulting from acid and aggregation-induced emission
Thin polymer film of performance and preparation method thereof.
Background technology
Changing color resulting from acid luminescent material refers under extraneous acid stimulation, and spectral color generates a kind of material substantially changeing,
There is important potential using value in fields such as optical recording, molecule sensing, molecular switch and luminescent devices.But it is traditional
Changing color resulting from acid luminescent material there are problems that under high concentration or solid state assemble fluorescent quenching, hinder changing color resulting from acid shine
Practical application of the material in the fields such as fluorescent switch and sensor.
2001, this loyalty seminar of Tang found molecule aggregation to 1-methyl-1,2,3,4,5-pentaphenyl-
The fluorescent emission of silole (MPPS) compound has positive effect.Just the opposite with conventional organic luminescence material, which exists
Hardly emit fluorescence in solution, but can but launch strong fluorescence in solid forms.Then they claim this phenomenon
For " aggregation-induced emission " (Aggregation-induced emission, AIE), and this material is called aggregation inducing hair
Luminescent material.AIE fundamentally solves the problems, such as the quenching of luminous organic material aggregation inducing, causes in organic light emission research field
Extensive concern.
The mainly organic molecule of changing color resulting from acid gathering induced luminescence material at present, however, under normal circumstances, it is organic
Small molecule needs that film can just be made by expensive equipment, and manufacturing cost is higher, and the poor mechanical property of film, limit its
Application on solid state device.
Invention content
The embodiment of the present invention provides a kind of thin polymer film and its system with changing color resulting from acid and aggregation-induced emission performance
Preparation Method, the thin polymer film not only have changing color resulting from acid performance and aggregation-induced emission performance, also good film forming characteristics.
A kind of preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance, the preparation method
Include the following steps：
The vinyl monomer with tetraphenyl ethylene group and benzothiazole group is synthesized, the vinyl monomer has changing color resulting from acid
With aggregation-induced emission performance, wherein the vinyl monomer is：
Conventional ethylene monomer, radical initiator and the vinyl monomer are placed in reaction dissolvent and carry out free-atom aqueous solution
Polymerization, to prepare copolymer material；
The copolymer material is dissolved using with volatile organic solvent, to obtain copolymer solution；
The copolymer solution is made by thin polymer film using volatilization membrane formation process.
It is described in the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention
Traditional vinyl monomer is：Methyl methacrylate, methyl acrylate, hydroxy-ethyl acrylate or styrene.
It is described in the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention
Radical initiator is：Azodiisobutyronitrile, benzoyl peroxide, di-t-butyl peroxide or diisopropyl peroxide.
It is described in the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention
Reaction dissolvent is：N,N dimethylformamide, toluene or dioxane.
In the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention, in institute
It states in conventional ethylene monomer and the vinyl monomer, the mass percent of the conventional ethylene monomer is 89%-98.9%, described
The mass percent of vinyl monomer is 1.1%-11%；
The ratio of the gross mass of the conventional ethylene monomer and the vinyl monomer and the quality of the radical initiator
Between 100-1000
It is described in the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention
Organic solvent is：Dichloromethane, tetrahydrofuran or acetone.
It is described in the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention
Conventional ethylene monomer, radical initiator and the vinyl monomer are placed in reaction dissolvent and carry out free radical solution polymerization, with
The step of preparing copolymer material, including：
Conventional ethylene monomer, radical initiator and the vinyl monomer are placed in polymerisation bottle, and reaction is added
Solvent fully dissolves；
Oxygen in the reaction bulb, heated sealed are displaced using drum nitrogen method；
For 24 hours, the reaction bulb is put into ice water for reaction, is terminated reaction, is used in combination n-hexane to precipitate, to obtain copolymer material
Material.
It is described in the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention
The step of synthesizing the vinyl monomer with tetraphenyl ethylene group and benzothiazole group, including：
6- hydroxyl -2- tetraphenyl ethylenes base-benzothiazole and dichloromethane are added in round-bottomed flask, nitrogen protection is passed through
Gas is cooled to 0 DEG C, is slowly added to acryloyl chloride, reacts 3h；
Water is added dropwise and reacts away excessive acryloyl chloride, adds a large amount of water extractions, and with dichloromethane and n-hexane volume
Than being 1:1 leacheate carries out column chromatography for separation, and vacuum rotary steam removes solvent, vacuum drying, to obtain with tetraphenyl ethylene base
The vinyl monomer of group and benzothiazole group.
It is described in the preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance of the present invention
Membrane formation process of volatilizing is spin-coating method or pull-rod coating method.
The present invention also provides a kind of thin polymer films with changing color resulting from acid and aggregation-induced emission performance, use above
The preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance is made.
Thin polymer film and preparation method thereof of the present invention with changing color resulting from acid and aggregation-induced emission performance leads to
It crosses conventional ethylene monomer and carries out free radical solution polymerization with changing color resulting from acid and the vinyl monomer of aggregation-induced emission performance,
The copolymer material with changing color resulting from acid and aggregation-induced emission performance is prepared, copolymer material is dissolved and passes through solvent
Thin polymer film is made in volatilization so that not only there is the thin polymer film of preparation apparent changing color resulting from acid performance and aggregation inducing to send out
Optical property, and there is excellent film forming；In addition, the preparation method of the thin polymer film, simple for process, manufacturing cost compared with
It is low.
Description of the drawings
To describe the technical solutions in the embodiments of the present invention more clearly, make required in being described below to embodiment
Attached drawing is briefly described, it should be apparent that, drawings in the following description are only some embodiments of the invention, for
For those skilled in the art, without creative efforts, it can also be obtained according to these attached drawings other attached
Figure.
Fig. 1 is the preparation side of the polymer provided in an embodiment of the present invention with changing color resulting from acid and aggregation-induced emission performance
The step schematic diagram of method；
Fig. 2 is the preparation side of the polymer provided in an embodiment of the present invention with changing color resulting from acid and aggregation-induced emission performance
The specific steps schematic diagram of the step S101 of method；
Fig. 3 is the preparation side of the polymer provided in an embodiment of the present invention with changing color resulting from acid and aggregation-induced emission performance
The specific steps schematic diagram of the step S102 of method.
Specific implementation mode
Following will be combined with the drawings in the embodiments of the present invention, and technical solution in the embodiment of the present invention carries out clear, complete
Site preparation describes.Obviously, described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.It is based on
Embodiment in the present invention, the every other implementation that those skilled in the art are obtained without creative efforts
Example, shall fall within the protection scope of the present invention.
Referring to Fig. 1, Fig. 1 is the polymerization provided in an embodiment of the present invention with changing color resulting from acid and aggregation-induced emission performance
The step schematic diagram of the preparation method of object.As shown in Figure 1, provided in an embodiment of the present invention there is changing color resulting from acid and aggregation inducing to send out
The preparation method of the thin polymer film of optical property, the preparation method include the following steps：
Step S101 synthesizes the vinyl monomer with tetraphenyl ethylene group and benzothiazole group；
Conventional ethylene monomer, radical initiator and the vinyl monomer are placed in reaction dissolvent and carry out by step S102
Free radical solution polymerization, to prepare copolymer material；
The copolymer material is dissolved using with volatile organic solvent, obtains copolymer solution by step S103；
Using volatilization membrane formation process thin polymer film is made in the copolymer solution by step S104.
Specifically, in step S101, can should be with the vinyl monomer of tetraphenyl ethylene group and benzothiazole groupIt is worth noting that, the vinyl monomer have changing color resulting from acid performance and
Aggregation-induced emission performance, transmitting fluorescence is weaker in the solution, but in state of aggregation or solid, can launch strong glimmering
Light.
Further, referring to Fig. 2, Fig. 2 has changing color resulting from acid and aggregation-induced emission to be provided in an embodiment of the present invention
The specific steps schematic diagram of the step S101 of the preparation method of the polymer of performance.As shown in Figure 1, Figure 2, step S101 is specific
Including：
6- hydroxyl -2- tetraphenyl ethylenes base-benzothiazole and dichloromethane are added in round-bottomed flask by step S1011, are led to
Enter nitrogen protection gas, be cooled to 0 DEG C, be slowly added to acryloyl chloride, reacts 3h；
Step S1012 is added dropwise water and reacts away excessive acryloyl chloride, adds the extraction of a large amount of water, and with dichloromethane and
N-hexane volume ratio is 1:1 leacheate carries out column chromatography for separation, and vacuum rotary steam removes solvent, vacuum drying, to be had
The vinyl monomer of tetraphenyl ethylene group and benzothiazole group.
In step s 102, conventional ethylene monomer, radical initiator and the vinyl monomer are placed in reaction dissolvent
Free radical solution polymerization is carried out, to prepare copolymer material.
Wherein, the conventional ethylene monomer that the embodiment of the present invention refers to can be：Methyl methacrylate, methyl acrylate,
Hydroxy-ethyl acrylate or styrene etc..The embodiment of the present invention passes through in the ethylene with tetraphenyl ethylene group and benzothiazole group
Monomer and the copolymerization of conventional ethylene monomer, have saved cost.
The radical initiator that the embodiment of the present invention refers to can be：Azodiisobutyronitrile, benzoyl peroxide, peroxidating
Di-t-butyl or diisopropyl peroxide etc..
The reaction dissolvent that the embodiment of the present invention refers to can be：N, N dimethyl toluene, toluene or dioxane etc..
Preferably, in the conventional ethylene monomer and the vinyl monomer, the quality percentage of the conventional ethylene monomer
Than being 1.1%-11% for the mass percent of 89%-98.9%, the vinyl monomer；The conventional ethylene monomer and the second
The ratio of the gross mass of alkene monomer and the quality of the radical initiator is between 100-1000.
Further, referring to Fig. 3, Fig. 3 has changing color resulting from acid and aggregation-induced emission to be provided in an embodiment of the present invention
The specific steps schematic diagram of the step S102 of the preparation method of the polymer of performance.Referring to figs 1 and 3, step S102 is specific
Including：
Conventional ethylene monomer, radical initiator and the vinyl monomer are placed in polymerisation bottle by step S1021,
And reaction dissolvent is added and fully dissolves；
Step S1022 displaces the oxygen in the reaction bulb, heated sealed using drum nitrogen method；
For 24 hours, the reaction bulb is put into ice water for step S1023, reaction, terminates reaction, n-hexane is used in combination to precipitate, with
To copolymer material.
In step s 103, the copolymer material is dissolved using with volatile organic solvent, to generate copolymerization
Object solution.Wherein, which can be：Dichloromethane, tetrahydrofuran or acetone etc..
In step S104, the copolymer solution is made by thin polymer film using volatilization membrane formation process.Wherein, the volatilization
Membrane formation process is spin-coating method or pull-rod coating method.
Below by way of specific examples of the implementation, the invention will be further elaborated, but the present invention is not limited thereto particular case
Son.
Embodiment 1
(1) vinyl monomer of the synthesis with tetraphenyl ethylene group and benzothiazole group：
The dichloromethane of 6- hydroxyl -2- tetraphenyl ethylenes base-benzothiazole (19.26g, 40.00mmol) and 100mL are added
Into the round-bottomed flask of 250.0mL, it is passed through nitrogen protection gas, is cooled to 0 DEG C, is slowly added to the acryloyl chloride of 4.0mL, stirring is anti-
3h is answered, reaction solution is poured into water, three times with dichloromethane extraction, organic layer is dried with anhydrous sodium sulfate, and vacuum rotary steam removes
Solvent, using the Methods For Purification of silica gel column chromatography, i.e., with dichloromethane and n-hexane volume ratio for 1:1 leacheate carries out column layer
Analysis separation, vacuum rotary steam remove solvent, and vacuum drying obtains 18.85g light yellow solids.
(2) conventional ethylene monomer, radical initiator and the vinyl monomer are placed in reaction dissolvent and carry out free radical
Polymerisation in solution, to generate copolymer material：
Take vinyl monomer (0.54g, 1.0mmol), the metering system with tetraphenyl ethylene group and benzothiazole group
Sour methyl esters (9.89g, 98.9mmol), azodiisobutyronitrile (0.02g, 0.1mmol) are placed in 50mL polymerisation bottles, are added
15mL dimethylformamides fully dissolve, and displace oxygen using drum nitrogen method, seal, are heated to 70 DEG C of reactions for 24 hours, are put into
Reaction is terminated in ice water, three times with a large amount of n-hexanes precipitation, obtains 8.90g light yellow solid powder.
(3) using having volatile organic solvent to dissolve the copolymer material, to obtain copolymer solution：
A certain amount of light yellow solid powder is fully dissolved with dichloromethane, obtains pale yellow transparent copolymer mixture
Liquid.
(4) copolymer solution is made by thin polymer film using volatilization membrane formation process：
Copolymer mixture is sealed into static 2h, copolymer mixture whirler spin-coating dries film,
Obtain thin polymer film.
Embodiment 2
(1) vinyl monomer of the synthesis with tetraphenyl ethylene group and benzothiazole group：
The dichloromethane of 6- hydroxyl -2- tetraphenyl ethylenes base-benzothiazole (19.26g, 40.00mmol) and 100mL are added
Into the round-bottomed flask of 250.0mL, it is cooled to 0 DEG C, the acryloyl chloride of 4.0mL is slowly added to, is stirred to react 3h, reaction solution is fallen
Enter in water, three times with dichloromethane extraction, organic layer is dried with anhydrous sodium sulfate, and vacuum rotary steam removes solvent, utilizes silicagel column
The Methods For Purification of chromatography, i.e., with dichloromethane and n-hexane volume ratio for 1:1 leacheate carries out column chromatography for separation, vacuum rotary steam
Solvent is removed, vacuum drying obtains 18.85g light yellow solids.
(2) conventional ethylene monomer, radical initiator and the vinyl monomer are placed in reaction dissolvent and carry out free radical
Polymerisation in solution, to generate copolymer material：
Take vinyl monomer (1.08g, 2.0mmol), the metering system with tetraphenyl ethylene group and benzothiazole group
Sour methyl esters (9.79g, 97.9mmol), azodiisobutyronitrile (0.02g, 0.1mmol) are placed in 50mL polymerisation bottles, are added
15mL dimethylformamides fully dissolve, and displace oxygen using drum nitrogen method, seal, are heated to 70 DEG C of reactions for 24 hours, are put into
Reaction is terminated in ice water, three times with a large amount of n-hexanes precipitation, obtains 9.80g light yellow solid powder.
(3) using having volatile organic solvent to dissolve the copolymer material, to obtain copolymer solution：
A certain amount of light yellow solid powder is fully dissolved with dichloromethane, obtains pale yellow transparent copolymer mixture
Liquid.
(4) copolymer solution is made by thin polymer film using volatilization membrane formation process：
Copolymer mixture is sealed into static 2h, copolymer mixture whirler spin-coating dries film,
Obtain thin polymer film.
Embodiment 3
(1) vinyl monomer of the synthesis with tetraphenyl ethylene group and benzothiazole group：
The dichloromethane of 6- hydroxyl -2- tetraphenyl ethylenes base-benzothiazole (19.26g, 40.00mmol) and 100mL are added
Into the round-bottomed flask of 250.0mL, it is cooled to 0 DEG C, the acryloyl chloride of 4.0mL is slowly added to, is stirred to react 3h, reaction solution is fallen
Enter in water, three times with dichloromethane extraction, organic layer is dried with anhydrous sodium sulfate, and vacuum rotary steam removes solvent, utilizes silicagel column
The Methods For Purification of chromatography, i.e., with dichloromethane and n-hexane volume ratio for 1:1 leacheate carries out column chromatography for separation, vacuum rotary steam
Solvent is removed, vacuum drying obtains 18.85g light yellow solids.
(2) conventional ethylene monomer, radical initiator and the vinyl monomer are placed in reaction dissolvent and carry out free radical
Polymerisation in solution, to generate copolymer material：
Take vinyl monomer (2.16g, 4.0mmol), the metering system with tetraphenyl ethylene group and benzothiazole group
Sour methyl esters (9.59g, 95.9mmol), azodiisobutyronitrile (0.02g, 0.1mmol) are placed in 50mL polymerisation bottles, are added
15mL dimethylformamides fully dissolve, and displace oxygen using drum nitrogen method, seal, are heated to 70 DEG C of reactions for 24 hours, are put into
Reaction is terminated in ice water, three times with a large amount of n-hexanes precipitation, obtains 10.24g light yellow solid powder.
(3) using having volatile organic solvent to dissolve the copolymer material, to generate copolymer solution：
A certain amount of light yellow solid powder is fully dissolved with dichloromethane, obtains pale yellow transparent copolymer mixture
Liquid.
(4) copolymer solution is made by thin polymer film using volatilization membrane formation process：
Copolymer mixture is sealed into static 2h, copolymer mixture whirler spin-coating dries film,
Obtain thin polymer film.
Embodiment 4
(1) vinyl monomer of the synthesis with tetraphenyl ethylene group and benzothiazole group：
The dichloromethane of 6- hydroxyl -2- tetraphenyl ethylenes base-benzothiazole (19.26g, 40.00mmol) and 100mL are added
Into the round-bottomed flask of 250.0mL, it is cooled to 0 DEG C, the acryloyl chloride of 4.0mL is slowly added to, is stirred to react 3h, reaction solution is fallen
Enter in water, three times with dichloromethane extraction, organic layer is dried with anhydrous sodium sulfate, and vacuum rotary steam removes solvent, utilizes silicagel column
The Methods For Purification of chromatography, i.e., with dichloromethane and n-hexane volume ratio for 1:1 leacheate carries out column chromatography for separation, vacuum rotary steam
Solvent is removed, vacuum drying obtains 18.85g light yellow solids.
(2) conventional ethylene monomer, radical initiator and the vinyl monomer are placed in reaction dissolvent and carry out free radical
Polymerisation in solution, to generate copolymer material：
Take vinyl monomer (3.24g, 6.0mmol), the metering system with tetraphenyl ethylene group and benzothiazole group
Sour methyl esters (9.39g, 93.9mmol), azodiisobutyronitrile (0.02g, 0.1mmol) are placed in 50mL polymerisation bottles, are added
15mL dimethylformamides (DMF) fully dissolve, and displace oxygen using drum nitrogen method, seal, are heated to 70 DEG C of reactions for 24 hours,
It is put into ice water and terminates reaction, three times with a large amount of n-hexanes precipitation, obtain 10.50g light yellow solid powder.
(3) using having volatile organic solvent to dissolve the copolymer material, to generate copolymer solution：
A certain amount of light yellow solid powder is fully dissolved with dichloromethane, obtains pale yellow transparent copolymer mixture
Liquid.
(4) copolymer solution is made by thin polymer film using volatilization membrane formation process：
Copolymer mixture is sealed into static 2h, copolymer mixture whirler spin-coating dries film,
Obtain thin polymer film.
The preparation method of thin polymer film of the present invention with changing color resulting from acid and aggregation-induced emission performance, passes through
Conventional ethylene monomer, radical initiator and vinyl monomer are placed in reaction dissolvent and carry out free radical solution polymerization, is generated altogether
Polymer material, and thin polymer film is made in copolymer material dissolving so that the thin polymer film of the generation thin polymer film is not
Only there is changing color resulting from acid performance and aggregation-induced emission performance, also good film forming characteristics；In addition, the system of the thin polymer film
Preparation Method, simple for process, manufacturing cost is relatively low.
Claims (10)
1. a kind of preparation method of the thin polymer film with changing color resulting from acid and aggregation-induced emission performance, which is characterized in that institute
Preparation method is stated to include the following steps：
The vinyl monomer with tetraphenyl ethylene group and benzothiazole group is synthesized, the vinyl monomer has changing color resulting from acid and gathers
Collect induced luminescence performance, wherein the vinyl monomer is：
Conventional ethylene monomer, radical initiator and the vinyl monomer are placed in progress free-atom aqueous solution in reaction dissolvent to gather
It closes, to prepare copolymer material；
The copolymer material is dissolved using with volatile organic solvent, obtains copolymer solution；
The copolymer solution is made by thin polymer film using volatilization membrane formation process.
2. the preparation side of the thin polymer film according to claim 1 with changing color resulting from acid and aggregation-induced emission performance
Method, which is characterized in that traditional vinyl monomer is：Methyl methacrylate, methyl acrylate, hydroxy-ethyl acrylate or benzene
Ethylene.
3. the preparation side of the thin polymer film according to claim 1 with changing color resulting from acid and aggregation-induced emission performance
Method, which is characterized in that the radical initiator is：Azodiisobutyronitrile, benzoyl peroxide, di-t-butyl peroxide or mistake
Aoxidize diisopropyl.
4. the preparation side of the thin polymer film according to claim 1 with changing color resulting from acid and aggregation-induced emission performance
Method, which is characterized in that the reaction dissolvent is：N,N-Dimethylformamide, toluene or dioxane.
5. according to thin polymer film of the claim 1-4 any one of them with changing color resulting from acid and aggregation-induced emission performance
Preparation method, which is characterized in that in the conventional ethylene monomer and the vinyl monomer, the quality of the conventional ethylene monomer
Percentage is 89%-98.9%, and the mass percent of the vinyl monomer is 1.1%-11%；
The ratio of the quality of the gross mass of the conventional ethylene monomer and the vinyl monomer and the radical initiator between
Between 100-1000.
6. the preparation side of the thin polymer film according to claim 1 with changing color resulting from acid and aggregation-induced emission performance
Method, which is characterized in that the organic solvent is：Dichloromethane, tetrahydrofuran or acetone.
7. the preparation side of the thin polymer film according to claim 1 with changing color resulting from acid and aggregation-induced emission performance
Method, which is characterized in that described conventional ethylene monomer, radical initiator and the vinyl monomer are placed in reaction dissolvent carries out
Free radical solution polymerization, the step of to prepare copolymer material, including：
Conventional ethylene monomer, radical initiator and the vinyl monomer are placed in polymerisation bottle, and reaction dissolvent is added
Fully dissolving；
Oxygen in the reaction bulb, heated sealed are displaced using drum nitrogen method；
For 24 hours, the reaction bulb is put into ice water for reaction, is terminated reaction, is used in combination n-hexane to precipitate, to obtain copolymer material.
8. the preparation side of the thin polymer film according to claim 1 with changing color resulting from acid and aggregation-induced emission performance
Method, which is characterized in that the synthesis has the step of vinyl monomer of tetraphenyl ethylene group and benzothiazole group, including：
6- hydroxyl -2- tetraphenyl ethylenes base-benzothiazole and dichloromethane are added in round-bottomed flask, nitrogen protection gas is passed through,
It is cooled to 0 DEG C, is slowly added to acryloyl chloride, reacts 3h；
Water is added dropwise and reacts away excessive acryloyl chloride, adds a large amount of water extractions, and be with dichloromethane and n-hexane volume ratio
1:1 leacheate carries out column chromatography for separation, and vacuum rotary steam removes solvent, vacuum drying, to obtain with tetraphenyl ethylene group and
The vinyl monomer of benzothiazole group.
9. the preparation side of the thin polymer film according to claim 1 with changing color resulting from acid and aggregation-induced emission performance
Method, which is characterized in that the volatilization membrane formation process is spin-coating method or pull-rod coating method.
10. a kind of thin polymer film with changing color resulting from acid and aggregation-induced emission performance, which is characterized in that wanted using such as right
Ask 1~9 any one of them that there is changing color resulting from acid and the preparation method of the thin polymer film of aggregation-induced emission performance to be made.
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| CN113861099A (en) * | 2021-09-30 | 2021-12-31 | 香港中文大学（深圳） | Free radical initiator, luminescent free radical polymer and preparation method thereof |
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| CN107793652A (en) * | 2017-11-23 | 2018-03-13 | 贵州理工学院 | Thin polymer film with changing color resulting from acid and aggregation-induced emission performance and preparation method thereof |
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| CN103804318A (en) * | 2014-02-14 | 2014-05-21 | 中山大学 | Benzothiazole derivative containing triphenylethylene or tetraphenylethylene structure and having aggregation-induced emission property and preparation method and application thereof |
| CN107793652A (en) * | 2017-11-23 | 2018-03-13 | 贵州理工学院 | Thin polymer film with changing color resulting from acid and aggregation-induced emission performance and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113861099A (en) * | 2021-09-30 | 2021-12-31 | 香港中文大学（深圳） | Free radical initiator, luminescent free radical polymer and preparation method thereof |
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Application publication date: 20180904 |