CN105801851A - Preparation method of electrochromic polyaniline derivative containing triphenylethylene structure on principal-chain nitrogen atom - Google Patents
Preparation method of electrochromic polyaniline derivative containing triphenylethylene structure on principal-chain nitrogen atom Download PDFInfo
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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
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
- C08G73/0266—Polyanilines or derivatives thereof
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K9/00—Tenebrescent materials, i.e. materials for which the range of wavelengths for energy absorption is changed as a result of excitation by some form of energy
- C09K9/02—Organic tenebrescent materials
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
Abstract
The invention discloses a preparation method of an electrochromic polyaniline derivative containing a triphenylethylene structure on a principal-chain nitrogen atom. According to the preparation method of the electrochromic polyaniline derivative containing the triphenylethylene structure on the principal-chain nitrogen atom, diphenylamine, tetrabutylammonium tribromide and di-tert-butyl dicarbonate are used as raw materials. The preparation method of the electrochromic polyaniline derivative containing the triphenylethylene structure on the principal-chain nitrogen atom comprises the following steps of firstly, making the diphenylamine and the tetrabutylammonium tribromide generate a halogenating reaction in a heating condition to obtain di(4-bromophenyl)amine; secondly, making the di(4-bromophenyl)amine and the di-tert-butyl dicarbonate generate a tert-butoxycarbonylation reaction under the action of a catalyst to obtain N-tert-butyloxycarbonyl-di(4-bromophenyl)amine; finally, making the N-tert-butyloxycarbonyl-di(4-bromophenyl)amine and a phenylamine compound containing the triphenylethylene structure generate an amination reaction under the action of a catalyst to obtain a polyaniline derivative containing the triphenylethylene structure on principal-chain nitrogen atom. The method is simple, and a product is uniform and further easy-control in components and better in solubility. An obtained thin polymer film is low in driving voltage and short in response time, can be applied to a smart window, a display, an electrochromic camouflage device and the like, and has a wide application prospect.
Description
Technical field
The invention belongs to electrochromic material field, be specifically related on a kind of backbone nitrogen atom contain
There is the preparation method of the electrochromic polyanilines derivant of triphenyl thylene structure.
Background technology
Electrochromic material refers under DC Electric Field, optical property (absorbance, reflection
Rate, absorbance and emissivity etc.) produce in visible wavelength range stable reversible change,
Appearance property then shows as color and the reversible change material of transparency.By applying difference
Voltage, off-color material can with ambient brightness change and change self brightness and colourity, with ensure
Target is in consistent state at any time with background, thus in the field such as camouflage, intellectual material
Have broad application prospects.
In numerous electrochromic materials, polyaniline has good electric conductivity, environmental stability
And cheap price, but owing to its solubility property, processability and physical property are poor etc.
Problem limits its application and development.Scholars more both domestic and external began attempt to lead to from 2002
Cross aniline and other monomer copolymerization or in polyaniline structure, introduce certain substituent group generation
Polyaniline derivative carries out the structurally-modified of polyaniline and modifies, thus effectively improves above
Defect.But these are explored and research have ignored scope and the controllability that polyaniline color changes, and make
Obtain it to be restricted in the application of some color region of variation.Additionally, in existing Electrochromic device,
Colourity and the brightness stability variant with ambient background, variable color of polyaniline optically variable films is bad
And there is the problem that film forming is irregular, thus significantly limit it in electrochromism camouflage device
Application.
The present invention contains the electroluminescent change of triphenyl thylene structure by preparing on a kind of backbone nitrogen atom
Color polyaniline derivative material and thin film thereof, be possible not only to brightness and the colourity of thin film, carry
The stability of high variable color, and dissolubility and the film property of polyaniline can be improved, to solving mesh
Front military engineering camouflage color can not have weight with surrounding and the technical barrier of seasonal variations
Want practical value.
Summary of the invention
The present invention is directed to the above-mentioned problems in the prior art, it is provided that a kind of backbone nitrogen atom
The preparation method of the upper electrochromic polyanilines derivant containing triphenyl thylene structure.
The preparation method of the present invention includes:
Step 1: diphenylamines and tetrabutyl tribromide ammonium are occurred halogenating reaction in a heated condition
Obtain two (4-bromophenyl) amine；
Step 2: two (4-bromophenyl) amine and Bis(tert-butoxycarbonyl)oxide are under the effect of catalyst
T-butoxycarbonylating reaction is occurred to obtain N-tertbutyloxycarbonyl-two (4-bromophenyl) amine；
Step 3:N-tertbutyloxycarbonyl-two (4-bromophenyl) amine and the benzene containing triphenyl thylene structure
Amines occurs aminating reaction to obtain on backbone nitrogen atom containing three under the effect of catalyst
The polyaniline derivative of styryl structures.
Above-mentioned preparation method, wherein, step 1 reaction dissolvent selected from chloroform, toluene, four
Hydrogen furan or its mixture；Diphenylamines and tetrabutyl tribromide ammonium molar ratio are 1:1～1:4,
Response time is 0.5～6 hour, and reaction temperature is 15～35 DEG C.
Specifically, step 1 is: diphenylamines, tetrabutyl tribromide ammonium and chloroform are added
Entering in there-necked flask, diphenylamines and tetrabutyl tribromide ammonium molar ratio are 1:1～1:4,
Evacuation is passed through argon.Being controlled by mixture temperature between 15～35 DEG C, reaction 0.5～6 is little
Time, with 1～7% sodium thiosulfate solution wash this solution, then wash with water to pH value be 7.
Evaporation chloroform, is dissolved in mixture in ether, and several times, anhydrous sodium sulfate is done in washing
Dry, rotary evaporation removes solvent, and crude by column chromatography obtains two (4-bromophenyl) amine.
Above-mentioned preparation method, in step 2, catalyst is 4-(dimethylamino) pyridine, reacts molten
Agent is selected from chloroform, oxolane, dichloromethane, toluene or its mixture；Two (4-
Bromophenyl) amine and Bis(tert-butoxycarbonyl)oxide molar ratio be 1:1～1:5, catalyst 4-(two
Methylamino) 0.1～0.5 times of the amount that consumption is two (4-bromophenyl) amine material of pyridine；Instead
Being 0.5～8 hour between Ying Shi, reaction temperature is 60～110 DEG C.
Specifically, step 2 is: by two (4-bromophenyl) amine, Bis(tert-butoxycarbonyl)oxide,
4-(dimethylamino) pyridine and oxolane join in there-necked flask, and evacuation is also passed through argon
Gas shielded.Two (4-bromophenyl) amine and Bis(tert-butoxycarbonyl)oxide molar ratio are 1:1～1:5,
The consumption of catalyst 4-(dimethylamino) pyridine is the amount of two (4-bromophenyl) amine material
0.1～0.5 times.Gained solution is heated to 60～110 DEG C reflux 0.5～8 hour, then cools down
To room temperature, rotary evaporation removes solvent, and crude by column chromatography obtains N-tertbutyloxycarbonyl-two
(4-bromophenyl) amine.
Above-mentioned preparation method, in step 3, catalyst is three (two benzal-BASE acetone) two palladiums,
Reaction dissolvent is selected from dichloromethane, toluene, oxolane, hexane or its mixture；The tertiary fourth of N-
Oxygen carbonyl-two (4-bromophenyl) amine and aniline compound containing triphenyl thylene structure feed intake mole
Ratio is 1:1～1:4, and the consumption of catalyst three (two benzal-BASE acetone) two palladiums is the tertiary fourth of N-
0.01～0.06 times of the amount of oxygen carbonyl-two (4-bromophenyl) amine material；Tri-butyl phosphine with
N-tertbutyloxycarbonyl-two (4-bromophenyl) amine molar ratio is 1:2～1:10, sodium tert-butoxide
Consumption is 2～7 times of the amount of N-tertbutyloxycarbonyl-two (4-bromophenyl) amine material；During reaction
Between be 24～72 hours, reaction temperature is 80～110 DEG C.Aniline containing triphenyl thylene structure
Compound is 4 '-(3-aminophenyl) triphenylethylenes, 4 '-(3-aminophenyl) tetraphenyl ethylenes, 4 '-(4-
Aminophenyl) triphenylethylene, 4 '-(4-aminophenyl) tetraphenyl ethylenes, carbazyl aminophenyl triphen second
Ene derivative and other triphenylethylene derivatives containing aminophenyl or its mixture.
Specifically, step 3 is: by N-tertbutyloxycarbonyl-two (4-bromophenyl) amine, contain
The aniline compound of triphenyl thylene structure and toluene join in there-necked flask, N-tertbutyloxycarbonyl
-two (4-bromophenyl) amine with the aniline compound molar ratio containing triphenyl thylene structure is
1:1～1:4.Three (two benzal-BASE acetone) two palladiums, three uncles it are separately added in this solution
Butyl phosphine and sodium tert-butoxide.The consumption of catalyst three (two benzal-BASE acetone) two palladiums is
0.01～0.06 times of the amount of N-tertbutyloxycarbonyl-two (4-bromophenyl) amine material, tri-tert
Phosphine and N-tertbutyloxycarbonyl-two (4-bromophenyl) amine molar ratio are 1:2～1:10, tertiary fourth
The consumption of sodium alkoxide is 2～7 times of the amount of N-tertbutyloxycarbonyl-two (4-bromophenyl) amine material.
Solution is heated to 80～110 DEG C, reacts 24～72 hours under argon shield.It is subsequently adding
5～50ml ammonia, are cooled to room temperature, wash several times with saturated nacl aqueous solution, anhydrous sulfur
Acid magnesium is dried.Rotary evaporation removes solvent, and crude product is poured in hexane precipitation, and washing leaches
Precipitation, obtain polymer powder after drying.
Using technique scheme, the present invention has obtained on a kind of backbone nitrogen atom containing triphen second
The preparation method of the electrochromic polyanilines derivant of alkene structure.This polymeric material can be with solution
Being sprayed on ito glass surface filming, after making device, the driving voltage of this polymeric material is low,
Response time is shorter, is highly suitable to be applied for the field such as smart window, electrochromism camouflage device.
The invention have the benefit that
The most whole safe preparation process, and operating process be prone to grasp.
2. product composition is easily controllable, and resulting polymers dissolubility is preferable.
3. polyaniline derivative thin film has good electric conductivity, and electrochromism has extended cycle life,
Fast response time.
Accompanying drawing explanation
Fig. 1 is the synthetic reaction route schematic diagram of polyaniline derivative (P1)；
Fig. 2 is the synthetic reaction route schematic diagram of polyaniline derivative (P2)；
Fig. 3 is the Fourier transform infrared spectrogram of compound 1；
Fig. 4 is the Fourier transform infrared spectrogram of 4 '-(3-aminophenyl) triphenylethylenes；
Fig. 5 is the Fourier transform infrared spectrogram of copolymer (P1)；
Fig. 6 is the nucleus magnetic hydrogen spectrum figure of copolymer (P1).
Detailed description of the invention
Below in conjunction with the accompanying drawings and the present invention is described in further details by embodiment.
Embodiment one:
N-tertbutyloxycarbonyl-two (4-bromophenyl) amine and 4 '-(3-aminophenyl) triphenylethylenes are handed over
Preparation for copolymer (P1):
The synthesis of (1) two (4-bromophenyl) amine
When 20 DEG C, by diphenylamines (0.017g, 0.1mmol) and tetrabutyl tribromide ammonium
(0.096g, 0.2mmol) joins in there-necked flask, and evacuation is passed through argon.With injection
Device adds 15ml chloroform soln in there-necked flask and stirs reaction half an hour, red
Mixture be quickly converted to colourless；This solution is washed, so with 3% sodium thiosulfate solution
After wash with water to pH value be 7.Boil off solvent, mixture is dissolved in 20ml ether, water
Washing several times, be dried with sodium sulfate, then rotary evaporation removes solvent.Pass through silicagel column
Chromatography purifies and obtains two (4-bromophenyl) amine, and productivity is 89%.
(2) synthesis of N-tertbutyloxycarbonyl-two (4-bromophenyl) amine
By two (4-bromophenyl) amine (0.327g, 1mmol) and 4-(dimethylamino) pyridine
(0.024g, 0.2mmol) Bis(tert-butoxycarbonyl)oxide (0.24ml, 1.1mmol) joins three
In mouth flask, evacuation is also passed through argon shield.Utilize syringe at addition in there-necked flask
The oxolane (20ml) managed.Gained solution is heated to 70 DEG C of backflow 1h, then by it
It is cooled to room temperature, by silica gel column chromatography isolated N-tertbutyloxycarbonyl-two (4-bromophenyl)
Amine, productivity is 76%.
The synthesis of (3) 4 '-(3-aminophenyl) triphenylethylenes
By 2-(4-bromophenyl)-1，1-diphenylethylene (0.336g, 1mmol) and 3-amino
Phenylboric acid (0.138g, 1mmol), tri-n-octyl methyl ammonium chloride (0.2g, 0.5mmol), 20ml
Toluene, the K of 2M2CO3Aqueous solution 5ml, joins in the there-necked flask of 50ml.To three
Mouth bottle evacuation logical argon shield, add tetrakis triphenylphosphine palladium after stirring 30min
(Pd(PPh3)4) (0.002g, 1.73 μm ol), evacuation leads to argon again.Oil bath is heated to
90 DEG C, reflux 24h.Extracting with water, organic facies anhydrous sodium sulfate is dried.Rotate and steam
Send out removing solvent and obtain crude product.The method using silica gel column chromatography carries out separating-purifying, and productivity is
60%.
(4) synthesis of copolymer p 1
By N-tertbutyloxycarbonyl-two (4-bromophenyl) amine (0.092g, 0.22mmol) and 4 '-
(3-aminophenyl) triphenylethylene (0.075g, 0.22mmol) dissolves under inert atmosphere conditions
In 15ml toluene.Three (two benzal-BASE acetone) it are separately added in this toluene solution
Two palladiums (0.005g, 5.39 μm ol), tri-butyl phosphine (0.007g, 0.03mmol) and tertiary fourth
Sodium alkoxide (0.062g, 0.65mmol).It is warming up to 95 DEG C, under argon shield, reacts 24h.It
After, add 10ml ammonia and make product be cooled to room temperature, by organic facies saturated nacl aqueous solution
Wash for several times, and dried over magnesium sulfate.Rotary evaporation removes solvent, and crude product is poured into oneself
Alkane makes copolymer precipitate, wash, with hexane, the precipitation leached and put in vacuum drying oven, warp
Obtaining polymer powder after drying, productivity is 88%.
Embodiment two:
N-tertbutyloxycarbonyl-two (4-bromophenyl) amine and 4 '-(3-aminophenyl) tetraphenyl ethylenes are handed over
Preparation for copolymer (P2):
(1) synthesis of 1-(4-bromophenyl)-1,2,2-triphenylethylene
Diphenyl methane (1.346g, 8.0mmol) is dissolved in anhydrous tetrahydro furan (20ml)
In, evacuation simultaneously, it is passed through argon shield.DEG C at, in above-mentioned solution add 2.2M
The hexane solution (3.64ml) of n-BuLi, after stirring reaction 1h, adds 4-bromine benzophenone
(1.671g, 6.4mmol).Continuing stirring 10h, reaction temperature gradually rises to room temperature.So
Rear addition aqueous ammonium chloride solution terminates reaction, and gained mixture dichloromethane extracts.Have
Machine layer is dried through anhydrous sodium sulfate, and rotary evaporation removes solvent and obtains thick alcohol.It is dissolved in
In toluene (32ml), add p-methyl benzenesulfonic acid (0.272g, 1.44mmol) backflow 12h.
Reactant mixture is cooled to room temperature, after evaporation, obtains crude product.With normal hexane as leacheate, adopt
Obtaining pale yellow powder with after silica gel column chromatography separating-purifying, productivity is 70%.
The synthesis of (2) 4 '-(3-aminophenyl) tetraphenyl ethylenes
By 1-(4-bromophenyl)-1,2,2-triphenylethylenes (0.822g, 2mmol) and 3-amino
Phenylboric acid (0.274g, 2mmol), tri-n-octyl methyl ammonium chloride (0.4g, 1mmol), 40ml
Toluene, the K of 2M2CO3Aqueous solution 10ml, joins in the there-necked flask of 100ml.Take out
Vacuum logical argon shield, add tetrakis triphenylphosphine palladium (Pd (PPh after stirring 30min3)4)
(0.004g, 3.46 μm ol), evacuation leads to argon again.Oil bath is heated to 90 DEG C, backflow
24h.Extracting with water, organic facies anhydrous sodium sulfate is dried.Rotary evaporation removes solvent
After crude product.The method utilizing silica gel column chromatography carries out separating-purifying, and productivity is 62%.
(3) synthesis of copolymer p 2
By N-tertbutyloxycarbonyl-two (4-bromophenyl) amine (0.092g, 0.22mmol) and 4 '-
(3-aminophenyl) tetraphenyl ethylene (0.093g, 0.22mmol) dissolves under inert atmosphere conditions
In 15ml toluene.Three (two benzal-BASE acetone) it are separately added in this toluene solution
Two palladiums (0.005g, 5.39 μm ol), tri-butyl phosphine (0.007g, 0.03mmol) and tertiary fourth
Sodium alkoxide (0.062g, 0.65mmol).It is warming up to 95 DEG C, under argon shield, reacts 24h.It
After, add 10ml ammonia and make product be cooled to room temperature, by organic facies saturated nacl aqueous solution
Wash for several times, and dried over magnesium sulfate.Rotary evaporation removes solvent, and crude product is poured into oneself
Alkane makes copolymer precipitate, wash the precipitation leached with hexane, obtain polymer powder after drying
End, productivity is 85%.
Above-described embodiment is only to be described the preferred embodiments of the present invention, not to this
Bright spirit and scope are defined, on the premise of without departing from design philosophy of the present invention, and ability
The various changes and modifications that in territory, technical scheme is made by professional and technical personnel, all belong to
In protection scope of the present invention.
Claims (4)
1. the electrochromic polyanilines containing triphenyl thylene structure on a backbone nitrogen atom derives
The preparation method of thing, including:
Step 1: diphenylamines and tetrabutyl tribromide ammonium are occurred halogenating reaction in a heated condition
Obtain two (4-bromophenyl) amine；
Step 2: two (4-bromophenyl) amine and Bis(tert-butoxycarbonyl)oxide are under the effect of catalyst
T-butoxycarbonylating reaction is occurred to obtain N-tertbutyloxycarbonyl-two (4-bromophenyl) amine；
Step 3:N-tertbutyloxycarbonyl-two (4-bromophenyl) amine and the benzene containing triphenyl thylene structure
Amines occurs aminating reaction to obtain on backbone nitrogen atom containing three under the effect of catalyst
The polyaniline derivative of styryl structures.
Method the most according to claim 1, it is characterised in that: step 1 is reacted molten
Agent is selected from chloroform, toluene, oxolane or its mixture；Diphenylamines and tetrabutyl tribromo
Changing ammonium molar ratio is 1:1～1:4, and the response time is 0.5～6 hour, and reaction temperature is
15～35 DEG C.
Method the most according to claim 1, it is characterised in that: catalyst in step 2
For 4-(dimethylamino) pyridine, reaction dissolvent is selected from chloroform, oxolane, dichloromethane
Alkane, toluene or its mixture；Two (4-bromophenyl) amine and Bis(tert-butoxycarbonyl)oxide feed intake mole
It is two (4-bromophenyls) than the consumption for 1:1～1:5, catalyst 4-(dimethylamino) pyridine
0.1～0.5 times of the amount of amine material；Response time is 0.5～8 hour, and reaction temperature is
60～110 DEG C.
Method the most according to claim 1, it is characterised in that: catalyst in step 3
Be three (two benzal-BASE acetone) two palladiums, reaction dissolvent selected from dichloromethane, toluene, four
Hydrogen furan, hexane or its mixture；N-tertbutyloxycarbonyl-two (4-bromophenyl) amine with containing three
The aniline compound molar ratio of styryl structures is 1:1～1:4, catalyst three (two benzal
-BASE acetone) consumption of two palladiums is N-tertbutyloxycarbonyl-two (4-bromophenyl) amine material
0.01～0.06 times of amount；Tri-butyl phosphine is thrown with N-tertbutyloxycarbonyl-two (4-bromophenyl) amine
Material mol ratio is 1:2～1:10, and the consumption of sodium tert-butoxide is N-tertbutyloxycarbonyl-two (4-bromobenzene
Base) 2～7 times of amount of amine material；Response time is 24～72 hours, and reaction temperature is
80～110 DEG C.Aniline compound containing triphenyl thylene structure is 4 '-(3-aminophenyl) triphen second
Alkene, 4 '-(3-aminophenyl) tetraphenyl ethylenes, 4 '-(4-aminophenyl) triphenylethylenes, 4 '-(4-
Aminophenyl) tetraphenyl ethylene, carbazyl aminophenyl triphenylethylene derivatives and other is containing aminophenyl
Triphenylethylene derivatives or its mixture.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101679206A (en) * | 2007-04-12 | 2010-03-24 | 日产化学工业株式会社 | Oligoaniline compound |
| CN104341311A (en) * | 2013-07-31 | 2015-02-11 | 中山大学 | Novel diamine compound, and preparation method and application thereof |
-
2016
- 2016-04-22 CN CN201610256488.3A patent/CN105801851A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101679206A (en) * | 2007-04-12 | 2010-03-24 | 日产化学工业株式会社 | Oligoaniline compound |
| CN104341311A (en) * | 2013-07-31 | 2015-02-11 | 中山大学 | Novel diamine compound, and preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| SAI MI ET AL: "AIEE-Active and Electrochromic Bifunctional Polymer and a Device Composed thereof Synchronously Achieve Electrochemical Fluorescence Switching and Electrochromic Switching", 《APPLIED MATERIALS & INTERFACES》 * |
| 张文治 等: "聚苯胺类电致变色材料的研究进展", 《高分子通报》 * |
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Application publication date: 20160727 |