CN108822297A - A kind of multi-color electrochromic polymer and its application in electrochromism field - Google Patents
A kind of multi-color electrochromic polymer and its application in electrochromism field Download PDFInfo
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- CN108822297A CN108822297A CN201810748549.7A CN201810748549A CN108822297A CN 108822297 A CN108822297 A CN 108822297A CN 201810748549 A CN201810748549 A CN 201810748549A CN 108822297 A CN108822297 A CN 108822297A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Abstract
A kind of novel multi-color electrochromic polymer and its application in electrochromism field that one kind is prepared by way of terpolymerization using purpurine and aniline oligomer as electrochromism primitive, belong to Functional polymer materials technology field.Polymer is to be prepared by pyromellitic acid anhydride monomer, anilino- diamine monomer and purpurine diamine monomer by terpolymerization reaction.The polymer material (- 0.8V~0V~0.8V) under lower driving voltage can produce the reversible color change of plurality of stable (purple~colourless~green~blue), have huge applications potentiality in electrochromic material field.
Description
Technical field
The invention belongs to functional polymer material fields, and in particular to a kind of using purpurine and aniline oligomer as electroluminescent change
Color base member, a kind of novel multi-color electrochromic polymer prepared by way of terpolymerization and its in electrochromism field
In application.
Background technique
Electrochromism refers to the optical properties (reflectivity, transmitance, absorptivity etc.) of material under the action of extra electric field
There is a phenomenon where stablizing, reversible change, show as the reversible change of color and transparency in appearance.With electrochromic property
Material be known as electrochromic material, electrochromic material is as a kind of novel functional material, gradually in smart window, low energy consumption
Display, automobile show wide application prospect from the multiple fields such as rearview mirror, intelligent wearable device are dimmed.
As the polyaniline of typical conducting polymer, since its electro-chemical activity is high, conversion voltage is low, good cycling stability
The advantages that, it is considered to be the most possible electrochromic polymeric compounds material for obtaining practical application.However due to big ruler in its molecule
Very little conjugated structure and intermolecular strong hydrogen bond action, makes polyaniline material not melt insoluble, poor in processability, and then serious influence
Practical application of the polyaniline material in electrochromism field.And the aniline oligomer as polyaniline model compound, due to
Its determine molecular structure, good dissolubility and with redox characteristic as polyaniline compound, cause numerous research works
The concern of person.The flexible MOLECULE DESIGN of aniline oligomer makes it can be used as electrochromism primitive to be introduced in polymer architecture
In, to obtain, a series of dissolubilities are good, the good anilino- electrochromic polymeric compounds material of processing performance.The quasi polymer
Substantially the electrochromic property of polyaniline material is maintained.
Purpurine is 1,1 '-disubstituted -4,4 '-connection pyrrole salt, in its structure there are two nitrogen-atoms different oxidations also
Ortho states, it is possible to provide electronics receives electronics, and oxidation-reduction reaction reversible twice can occur.There are three types of oxidations for purpurine tool also
Original state is that one kind common are machine small molecule cathodic coloration material along with color change in oxidation-reduction process.Mesh
Before, molecular modification is mostly focused on for the research of purpurine, solution type electrochromic device is prepared into, as electrochromism
The research that material is fixed in conductive substrates is also fewer.
Summary of the invention
Pass through three by purpurine monomer and the diamine monomer containing aniline oligomer segment the object of the present invention is to provide a kind of
Multi-color electrochromic polymer and its application in electrochromism field prepared by the mode of first combined polymerization.The polymer material
It can produce plurality of stable reversible color change (purple~colourless between lower driving voltage (- 0.8V~0V~0.8V)
~green~blue), there are huge applications potentiality in electrochromic material field.
Multi-color electrochromic polymer of the present invention, structural formula are shown below：
X, y are positive integer, 30≤x≤60,10≤y≤20
(Ⅰ)
The invention firstly uses the reduction-state parent aniline tetramers and difluoro benzoyl chloride to be contained by amidation process
Having double fluorine monomer F of aniline oligomer segment, (contents such as synthesis, characterization of the monomer are detailed in Chinese patent：
201010293748.7, side chain type electroactive polyarylether polymer and preparation method thereof), then by double fluorine monomer F and 4- amino
Phenol prepares electroactive anilino- diamine monomer M (during the contents such as synthesis, characterization of the monomer are detailed in by nucleophilic substitution
State's patent：201410010359.7 side chain type electroactive polyurea polymer, preparation method and its application in terms of anti-corrosion)；Its
Secondary, using three propantheline bromide hydrobromides and 4,4- bipyridyl reacts to obtain purpurine diamine monomer Z；Finally, by two kinds of diamine monomers
M, Z polymerize to obtain multi-color electrochromic polymer of the present invention with pyromellitic acid anhydride.
The preparation method of multi-color electrochromic polymer of the present invention, its step are as follows：
(1) synthesis of structural formula purpurine diamine monomer Z as shown in (III)：By molal quantity be 5 times of 4,4- bipyridyl three
Propantheline bromide hydrobromide is added in acetonitrile, and the solid content of reaction system is 10~20%, and back flow reaction 72 hours；It filters, it will
Obtained precipitating is with being dissolved in distilled water after ethanol washing 3 times, and it is 4,4- bipyridyl 4 that molal quantity, which is added, into solution
Times ammonium hexafluorophosphate, after ammonium hexafluorophosphate is completely dissolved to the sodium hydroxide solution of mixed solution and dripping 1M to there is no
White flock precipitate generates；It filters, obtained precipitating is washed with distilled water 3 times, 35~45 DEG C of dryings 24~36 of vacuum drying oven
Hour, obtain the purpurine diamine monomer Z for being dissolved in organic solvent；
(2) electroactive anilino- diamine monomer M, purpurine diamine monomer Z, pyromellitic acid anhydride are added to organic solvent
In (such as N-Methyl pyrrolidone, n,N-dimethylacetamide, N, N- dimethylformamide or dimethyl sulfoxide), reaction system contains admittedly
Amount is 10~20%；Wherein the mole ratio of electroactive anilino- diamine monomer M and purpurine diamine monomer Z is 1：3, equal benzene tetramethyl
The molal quantity of acid dianhydride is the sum of the molal quantity of diamine monomer M and Z, N2Protection lower room temperature reaction 10~12 hours；
(3) reaction product that step (2) obtains is poured into distilled water, filters, is washed respectively with distilled water and dehydrated alcohol
Product is washed, end product is dried in vacuo 24~36 hours at 35~45 DEG C, obtains structural formula multi-color electrochromic as shown in (I)
Polymer.
Wherein, the structural formula of anilino- diamine monomer M is：
The structural formula of purpurine diamine monomer Z is：
The structural formula of pyromellitic acid anhydride is：
Detailed description of the invention
Fig. 1：The nuclear magnetic spectrogram for the multi-color electrochromic polymer that the present invention synthesizes；
Fig. 2：The infrared spectrum of multi-color electrochromic polymer synthesized by the present invention；
Fig. 3：The cyclic voltammetry curve for the multi-color electrochromic thin polymer film that the present invention synthesizes；
Fig. 4：The electrochemical impedance for the multi-color electrochromic thin polymer film that the present invention synthesizes tests spectrogram；
Fig. 5:Ultraviolet-visible spectrum of the multi-color electrochromic thin polymer film that the present invention synthesizes under 0~0.8V voltage
Map；Illustration is color change figure of the thin polymer film when being passed through voltage and being 0V, 0.4V, 0.8V；
Fig. 6：In the case where alternately applying 0 and 0.8V voltage, the period is the multi-color electrochromic thin polymer film that the present invention synthesizes
30s, the uv absorption spectra under the 1-10 alternate voltages tested at the 720nm wavelength；
Fig. 7：UV-visible spectrum spectrum of the thin polymer film that the present invention synthesizes under -0.8~0V voltage；Illustration is
Color change figure of the thin polymer film when being passed through voltage and being -0.6V, 0V；
Fig. 8：The thin polymer film that the present invention synthesizes is in the case where alternately applying -0.8 and 0V voltage, period 30s, in 550nm
UV-visible spectrum under the 1-10 alternate voltages tested at wavelength；
The group as corresponding to the nuclear magnetic spectrogram and each signal peak that Fig. 1 is polymer,1H NMR(d6- DMSO, ppm), δ=
10.37 (m ,-CONH-), δ=9.45-8.30 (m, Ar-H in viologen), δ=7.70-6.30 (m, Ar-H), δ=4.86
(d,-CH2), δ=2.89 (m ,-CH2), δ=2.30 (m ,-CH2-).Wherein the proton signal peak at 10.37ppm corresponds to poly-
The hydrogen of amido bond in object is closed, 9.45-8.30ppm corresponds to the hydrogen in purpurine unit on pyridine ring, and 7.70-6.30ppm corresponds to
Hydrogen on phenyl ring, 4.86ppm, 2.89ppm are-CH in purpurine structure at 2.30ppm2On hydrogen.
As Fig. 2 polymer infrared spectroscopy in, 3253cm-1For the vibration absorption peak of amido.3045cm-1For on pyridine ring
The stretching vibration absworption peak of c h bond.1717cm-1For the stretching vibration absworption peak of carbonyl in amide structure.1599,1502 Hes
1451cm-1For the vibration absorption peak of C=C key in phenyl ring and pyridine ring.1297cm-1For C-N key chattering absorption peak.826,753 Hes
557cm-1For the characteristic absorption peak of c h bond on phenyl ring.
If Fig. 3 is multi-color electrochromic thin polymer film (thickness：Cyclic voltammogram 300nm).Using three-electrode system,
Polymer solution is coated in ITO substrate to (revolving speed is 900r/s 60s) by way of spin coating, work is used as after vacuum drying
Make electrode, platinum electrode is to electrode, and Ag/AgCl electrode is reference electrode, in the potassium chloride salt acid solution of the 1M of pH=2 into
Row test.Three pairs of redox peaks are shown in figure, the electricity at the place -0.54V/-0.44V is to the redox for purpurine diamine unit
Convert current potential.Electricity converts current potential to the redox between Oligoanilines reduction-state/intermediate oxidation state at 0.14V/0.32V.
Electricity converts current potential to the redox between Oligoanilines intermediate oxidation state/highest oxidation state at 0.38V/0.49V.
If Fig. 4 is multi-color electrochromic thin polymer film (thickness：Electrochemical impedance spectrogram 300nm).Select Randles
Equivalent circuit diagram simulated experiment data, the electrochemical impedance value for measuring the thin polymer film modified in ITO substrate is 14450 Ω.
It is illustrated in figure 5 UV-visible spectrum spectrum of the polymer under 0~0.8V voltage, first in polymer/ITO
Apply constant voltage 200s on electrode, current value is stablized.Redox transformation no longer occurs for the Oligoanilines in polymer.It should
Thin polymer film is placed in ultraviolet-visible spectrometer, its transmitance is tested in the wave-length coverage of 280-800nm.Illustration is shown
It is polymer/ITO working electrode by colourless (0V) to green (0.4V), then to the color transition of blue (0.8V).
Thin polymer film is illustrated in figure 6 under 0 and 0.8V alternate voltages, period 30s is tested at 720nm wavelength
The 1-10 alternate voltages under uv absorption spectra.Coloration time is defined as polymer to reach from bleaching state to coloured state
To the time needed for the 90% of color change, fading time is defined as polymer and reaches color change from coloured state to bleaching state
90% needed for the time.When as seen from the figure under the 1st~10 alternate voltages, the coloration time of polymer working electrode and take off
The color time is respectively 2.2s and 1.2s, coloration efficiency 40cm2/C。
It is illustrated in figure 7 UV-visible spectrum spectrum of the polymer under -0.8~0V voltage, first in polymer/ITO
Apply constant voltage 200s on electrode, current value is stablized.Redox transformation no longer occurs for the purpurine unit in polymer.It should
Polymer electrode is placed in ultraviolet-visible spectrometer, its transmitance is tested in the wave-length coverage of 280~800nm.Illustration is shown
It is changed into the color transition of purple (- 0.6V) by colourless (0V) for polymer/ITO working electrode.
Thin polymer film is illustrated in figure 8 under -0.8 and 0V alternate voltages, period 30s is tested at 550nm wavelength
The 1st~10 alternate voltages under UV-visible spectrum.Coloration time is defined as polymer from bleaching state to coloured state
Fading time is defined as polymer and reaches color change from coloured state to bleaching state by the time needed for reaching the 90% of color change
Time needed for 90% changed.When as seen from the figure under the 1st~10 alternate voltages, the coloration time of polymer working electrode and
Fading time is respectively 5.1s and 11.7s, coloration efficiency 22cm2/C。
Specific embodiment
Embodiment 1
The synthesis of structural formula purpurine diamine monomer Z as shown in (III)：The tribromo third for being 5 times of 4,4- bipyridyl by molal quantity
Amine hydrobromate is added in acetonitrile, and the solid content of reaction system is 20%, and back flow reaction 72 hours.It filters, will be precipitated
It is dissolved in distilled water afterwards twice with ethanol washing, and the hexafluoro that molal quantity is 4 times of 4,4- bipyridyl will be added in solution
Ammonium phosphate, to the sodium hydroxide solution of mixed solution and dripping 1M to there is no white flocks after ammonium hexafluorophosphate is completely dissolved
Precipitating generates.It filters, precipitating is washed with distilled water 3 times, the drying 30 hours of 40 DEG C of vacuum drying oven obtains being dissolved in organic solvent
Purpurine diamine monomer Z, yield 77%.
Electroactive anilino- diamine monomer M, purpurine diamine monomer Z, pyromellitic acid anhydride are added to N- methylpyrrole
In alkanone, reaction system solid content is 20%.Wherein the mole ratio of diamine monomer M and Z is 1:3, pyromellitic acid anhydride
Molal quantity is the sum of the molal quantity of diamine monomer M and Z.N2Protection lower room temperature reaction 10 hours.
Reaction product is poured into distilled water, is filtered, respectively with distilled water and dehydrated alcohol washed product, end product exists
40 DEG C are dried in vacuo 30 hours, obtain structural formula multi-color electrochromic polymer as shown in (I), yield 58%.
Claims (2)
1. a kind of multi-color electrochromic polymer, structural formula are as follows：
X, y are positive integer, 30≤x≤60,10≤y≤20.
2. a kind of application of the multi-color electrochromic polymer described in claim 1 in electrochromism field.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109762347A (en) * | 2019-01-24 | 2019-05-17 | 吉林大学 | It is a kind of by the multi-functional netted hybrid film material of covalent bonding and its in the application of electrochemical field |
| CN110437095A (en) * | 2019-07-29 | 2019-11-12 | 安阳工学院 | 2- (3- amino-benzene oxygen) -6- (4- amino-benzene oxygen)-N- (2- aminofluorene) benzamide monomer |
| WO2020232777A1 (en) * | 2019-05-21 | 2020-11-26 | 武汉华星光电半导体显示技术有限公司 | Electrochromic polyamic acid material, preparation method therefor, and display device |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109762347A (en) * | 2019-01-24 | 2019-05-17 | 吉林大学 | It is a kind of by the multi-functional netted hybrid film material of covalent bonding and its in the application of electrochemical field |
| CN109762347B (en) * | 2019-01-24 | 2020-12-01 | 吉林大学 | Multifunctional reticular hybrid film material bonded through covalent bond and application thereof in electrochemical field |
| WO2020232777A1 (en) * | 2019-05-21 | 2020-11-26 | 武汉华星光电半导体显示技术有限公司 | Electrochromic polyamic acid material, preparation method therefor, and display device |
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| CN110437095A (en) * | 2019-07-29 | 2019-11-12 | 安阳工学院 | 2- (3- amino-benzene oxygen) -6- (4- amino-benzene oxygen)-N- (2- aminofluorene) benzamide monomer |
| CN110437095B (en) * | 2019-07-29 | 2022-05-10 | 安阳工学院 | 2- (3-aminophenoxy) -6- (4-aminophenoxy) -N- (2-aminofluorene) benzamide monomer |
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