CN102329299B - Star-shaped oligothiophene derivative, preparation method and application thereof - Google Patents
Star-shaped oligothiophene derivative, preparation method and application thereof Download PDFInfo
- Publication number
- CN102329299B CN102329299B CN 201110192065 CN201110192065A CN102329299B CN 102329299 B CN102329299 B CN 102329299B CN 201110192065 CN201110192065 CN 201110192065 CN 201110192065 A CN201110192065 A CN 201110192065A CN 102329299 B CN102329299 B CN 102329299B
- Authority
- CN
- China
- Prior art keywords
- thienyl
- reaction
- benzene
- preparation
- star
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Landscapes
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Abstract
The invention provides a star-shaped oligothiophene derivative, a preparation method and application thereof. The derivative is 1, 3-di(2'-(5'-aldehyde)-thienyl)-5-(2'-thienyl)-benzene and is obtained by reacting N, N-dimethylformamide with phosphorus oxychloride, and then, reacting with 1, 3, 5-tri(2'-thienyl)-benzene, hydrolyzing a reaction product, sucking a filtrate and separating the filtrate. The derivative further can be 1, 3, 5-tri(2'-(5'-cyano)-thienyl)-benzene and is obtained by reacting a dichloromethane solution of the 1, 3, 5-tri(2'-thienyl)-benzene with chlorosulfonyl isocyanate, and then, reacting with the N, N-dimethylformamide, hydrolyzing, extracting and purifying a reaction product. The product prepared by the method has good chemical stability and environmental stability, and can be used as an organic electrochromic material to be used for assembling an organic electrochromic device. By using the product, the defects that an inorganic electrochromic material is difficult to form a film, is not suitable to be processed flexibly and cannot be degraded in toxicity are overcome.
Description
Technical field
The present invention relates to organic polymer photoelectric material technical field, be specifically related to star-shaped oligothiophene derivative and preparation method thereof and application.
Background technology
Electrochromism refers to that material produces stable reversible change phenomenon at the optical properties (transmissivity, reflectivity or specific absorption) of ultraviolet-visible light or near infrared region under DC Electric Field, show as the reversible change of color and transparency in appearance.Material with electrochromic property is called electrochromic material.Electrochromic material has been showed good application prospect in the fields such as dimming glass of demonstration, building energy conservation glass, anti-glare rear-view mirror for automobile, automobile or aircraft.And the polymerization degree and polymerization position can be controlled, high purity Uniformpoly thiophene with definite molecular weight, because of its five-membered ring structure, meet Huckel's rule, has moderate energy gap, wider spectral response, good environmental stability and thermostability in recent years, are used as functional organic material and research and develop.Up to the present, according to the research and development target of Uniformpoly thiophene as light, Electricity Functional organic materials, design, synthesized various Uniformpoly thiophene derivatives.These Uniformpoly thiophene derivatives mainly are used to the research of the following aspects: (1) studies the electric conductivity of resulting ion free radical salt with the relation of conjugate length by electrochemical doping; (2) the research and development Uniformpoly thiophene derivative is as the photoelectric characteristic of photoelectric conversion material; (3) the research Uniformpoly thiophene derivative is sent out the characteristics of luminescence of material as organic electroluminescent.
In view of Uniformpoly thiophene derivative is π-Department of Electronics's conjugate beam, the electric material of a class excellent performance, therefore, the kind and the Application Areas thereof that enlarge Uniformpoly thiophene derivative seem particularly important.
At present, electrochromic material almost is inorganic transition metal oxide entirely, and the manufacturing cost of inorganic electrochromic material is higher, is difficult for film forming, unsuitable flexible processing, and also some inorganic transition metal oxide also has nondegradable toxicity.
Summary of the invention
In order to solve defective and the deficiency of existing correlation technique, enlarge simultaneously kind and the Application Areas thereof of Uniformpoly thiophene derivative, the invention provides star-shaped oligothiophene derivative and preparation method thereof and application, prepared star-shaped oligothiophene derivative is easy to film forming, be easy to flexible processing, can be used as organic electrochromic material and be used for assembling organic electroluminescence variable color device.
Star-shaped oligothiophene derivative provided by the present invention is 1,3-two (2
'-(5
'-aldehyde radical)-thienyl)-5-(2
'-thienyl)-and benzene (referred to as 3TB-2CHO), have molecular structure as follows:
（1）
Its structural characterization data are as follows:
Mass spectrum: m/z 380.9 (M+);
Proton nmr spectra: δ (ppm): 9.96 (s, 2H), 8.15 ~ 8.05 (m, 4H), 8.03 (s, 3H), 7.85 (d, 1H), 7.71 (d, 1H), 7.25 (t, 1H);
Infrared spectra: (KBr method, cm
-1): 1650 (ν
C=O).
As another kind of structure, star-shaped oligothiophene derivative of the present invention is 1,3,5-three (2
'-(5
'-cyano group)-thienyl)-benzene (referred to as 3TB-3CN), have molecular structure as follows:
（2）
Its structural characterization data are as follows:
Mass spectrum: m/z 400.6 (M+);
Proton nmr spectra: δ (ppm): 7.98 (s, 3H), 7.71 (d, 3H), 7.26 (d, 3H);
Infrared spectra: (KBr method, cm
-1): 2265 (ν
C ≡ N).
The preparation process of described 3TB-2CHO is as follows:
(1) under the nitrogen protection, to
N,
NSlowly drip phosphorus oxychloride in the-dimethyl formamide, 30 ℃～65 ℃ of control temperature of reaction, stirring reaction 20 minutes～30 minutes obtains reaction solution;
(2) add 1,3,5-three (2 in the reaction solution that obtains to step (1)
'-thienyl)-and benzene, stirring reaction 35 minutes～45 minutes obtains reaction soln;
(3) add distilled water in the reaction soln that obtains to step (2) and be hydrolyzed, obtain flocks, be 3-two (2
'-(5
'-aldehyde radical)-thienyl)-5-(2
'-thienyl)-and the crude product of benzene, suction filtration goes out flocks, utilizes chromatographic column that crude product is separated, and namely obtains pure 3-two (2
'-(5
'-aldehyde radical)-thienyl)-5-(2
'-thienyl)-benzene.
The washing fluid of described chromatographic column adopting is toluene.
Described each preparation process is all carried out in microwave reactor.
Described 1,3,5-three (2
'-(5
'-cyano group)-thienyl)-preparation process of benzene is as follows:
(1) under the nitrogen protection, with 1,3,5-three (2
'-thienyl)-and benzene and methylene chloride mixing, get mixed solution; Slowly drip Sulfuryl chloride isocyanate in mixed solution, 30 ℃～65 ℃ of control temperature of reaction stirring reaction 40-60 minute, obtain reaction solution;
(2) add in the reaction solution that obtains to step (1)
N,
N-dimethyl formamide, stirring reaction 15 minutes～25 minutes obtains reaction soln;
(3) add the distilled water hydrolysis in the reaction soln that obtains to step (2), get hydrolyzed solution; Use the dichloromethane extraction hydrolyzed solution, the organic layer anhydrous sodium sulfate drying after the extraction, remove by filter sodium sulfate after, get filtrate; Behind the methylene dichloride in the pressure reducing and steaming filtrate, obtain 1,3,5-three (2
'-(5
'-cyano group)-thienyl)-crude product of benzene, crude product separates with chromatographic column, namely obtains purely 1,3, and 5-three (2
'-(5
'-cyano group)-thienyl)-benzene.
It is the mixed solvent of methylene dichloride and sherwood oil that described chromatographic column is separated the washing fluid that adopts.
Each step of described preparation is all carried out in microwave reactor.
The application of star-shaped oligothiophene derivative of the present invention in preparation organic electroluminescence variable color device, step; As follows:
The first step, the method for employing vacuum plating, at ITO conductive glass surface evaporation star-shaped oligothiophene derivative film, film thickness is 100nm～130nm;
Second step, take the perchloric acid 4-butyl amine as ionogen, acetonitrile is solvent, is mixed with electrolyte solution;
The 3rd step, having the ITO conductive glass of star-shaped oligothiophene derivative film and colourless transparent glass to be assembled into thickness with evaporation is 1 millimeter～1.5 millimeters electrolyzer, in groove, add the electrolyte solution of preparing, insert simultaneously diameter and be 0.5 millimeter～0.8 millimeter platinum line, respectively with ITO conductive glass and platinum line as electrode, be packaged into the organic electrochromic device
When apply+when 2.5 V and-2.5 V voltage, in the device, the 3TB-2CHO film can occur faint yellow and russet reversible change; When apply+when 1.9 V and-1.9 V voltage, in the device, the 3TB-3CN film can occur faint yellow and orange-red reversible change.
Compared with prior art, the present invention has following advantage:
(1) the inorganic electrochromic device that overcome with inorganic electrochromic material assembling of the present invention has the manufacturing cost height, is difficult for film forming, the unsuitable flexible shortcoming of processing and having non-degradable toxicity;
(2) the prepared star-shaped oligothiophene derivative of the present invention not only has better chemistry and environmental stability, and its oxidized and reduced is also more stable, and its electrochromic property also is stable.
Embodiment
Below in conjunction with embodiment, the present invention is done further detailed description, but be not limited to this.
Embodiment 1
1), the preparation of 3TB-2CHO:
The first step under the protection of nitrogen, adds in there-necked flask
N,
N-dimethyl formamide slowly drips phosphorus oxychloride, 30 ℃ of control temperature of reaction, and stirring reaction 65 minutes obtains reaction solution;
Second step adds 1,3,5-three (2 in above-mentioned reaction solution
'-thienyl)-and benzene, stirring reaction 35 minutes obtains reaction soln;
In the 3rd step, after reaction finishes, in the reaction soln of second step gained, add the distilled water hydrolysis, the flocks that obtains is the crude product of 3TB-2CHO, vacuum filtration goes out flocks, then with chromatographic column flocks is separated, and obtains the pure products of 3TB-2CHO.
The structural characterization data of 3TB-2CHO are as follows:
Mass spectrum: m/z 380.9 (M+);
Proton nmr spectra: δ (ppm): 9.96 (s, 2H), 8.15 ~ 8.05 (m, 4H), 8.03 (s, 3H), 7.85 (d, 1H), 7.71 (d, 1H), 7.25 (t, 1H).
Infrared spectra: (KBr method, cm
-1): 1650 (ν
C=O).
2), the preparation of 3TB-3CN:
The first step under the protection of nitrogen, adds 1,3,5-three (2 in there-necked flask
'-thienyl)-and benzene and methylene chloride, slowly drip Sulfuryl chloride isocyanate, 30 ℃ of control temperature of reaction, stirring reaction 65 minutes obtains reaction solution;
Second step adds in above-mentioned reaction solution
N,
N-dimethyl formamide, stirring reaction 15 minutes obtains reaction soln;
The 3rd step after reaction finishes, added the distilled water hydrolysis in the reaction soln of second step gained, the organic layer anhydrous sodium sulfate drying with using behind the dichloromethane extraction removes by filter sodium sulfate, gets filtrate; Methylene dichloride in the pressure reducing and steaming filtrate namely obtains the crude product of 3TB-3CN, then with chromatographic column crude product is carried out separating-purifying, obtains the pure products of 3TB-3CN.
Each step reaction of preparation 3TB-2CHO and 3TB-3CN is all carried out in microwave reactor.
For 3TB-2CHO, the washing fluid that chromatographic separation adopts is toluene; For 3TB-3CN, the washing fluid that chromatographic separation adopts is the mixed solvent of methylene dichloride and sherwood oil.
The structural characterization data of 3TB-3CN are as follows:
Mass spectrum: m/z 400.6 (M+);
Proton nmr spectra: δ (ppm): 7.98 (s, 3H), 7.71 (d, 3H), 7.26 (d, 3H);
Infrared spectra: (KBr method, cm
-1): 2265 (ν
C ≡ N).
3), the preparation of organic electrochromic device
The first step, the method for employing vacuum plating, at ITO conductive glass surface evaporation star-shaped oligothiophene derivative film, its thickness is 100nm.
Second step, take the perchloric acid 4-butyl amine as ionogen, acetonitrile is solvent, is mixed with electrolyte solution.
The 3rd step, having the ITO conductive glass of star-shaped oligothiophene derivative film and colourless transparent glass to be assembled into thickness with evaporation is 1 millimeter electrolyzer, in groove, add the electrolyte solution of preparing, insert simultaneously diameter and be 0.5 millimeter platinum line, respectively with electroconductive ITO glass and platinum line as electrode, be packaged into the organic electrochromic device.
The 4th step, when apply+when 2.5 V and-2.5 V voltage, in the device, the 3TB-2CHO film can occur faint yellow and russet reversible change; When apply+when 1.9 V and-1.9 V voltage, in the device, the 3TB-3CN film can occur faint yellow and orange-red reversible change;
Embodiment 2
1), the preparation of 3TB-2CHO:
The first step under the protection of nitrogen, adds in there-necked flask
N,
N-dimethyl formamide slowly drips phosphorus oxychloride, 45 ℃ of control temperature of reaction, and stirring reaction 40 minutes gets reaction solution;
Second step adds 1,3,5-three (2 in above-mentioned reaction solution
'-thienyl)-and benzene, stirring reaction 30 minutes obtains reaction soln;
The 3rd step after reaction finishes, added the distilled water hydrolysis in above-mentioned reaction soln, obtain flocks, and vacuum filtration goes out flocks, is the crude product of 3TB-2CHO, then separates with chromatographic column, obtains the pure products of 3TB-2CHO.
The structural characterization data of 3TB-2CHO are as follows:
Mass spectrum: m/z 380.9 (M+);
Proton nmr spectra: δ (ppm): 9.96 (s, 2H), 8.15 ~ 8.05 (m, 4H), 8.03 (s, 3H), 7.85 (d, 1H), 7.71 (d, 1H), 7.25 (t, 1H);
Infrared spectra: (KBr method, cm
-1): 1650 (ν
C=O).
2), the preparation of 3TB-3CN:
The first step under the protection of nitrogen, adds 1,3,5-three (2 in there-necked flask
'-thienyl)-and benzene and methylene chloride, slowly drip Sulfuryl chloride isocyanate, 45 ℃ of control temperature of reaction, stirring reaction 45 minutes gets reaction solution;
Second step adds in above-mentioned reaction solution
N,
N-dimethyl formamide, stirring reaction 20 minutes obtains reaction soln;
The 3rd step after reaction finishes, added the distilled water hydrolysis in above-mentioned reaction soln, with the organic layer anhydrous sodium sulfate drying behind the dichloromethane extraction, remove by filter sodium sulfate after, get filtrate; Methylene dichloride in the pressure reducing and steaming filtrate namely obtains the crude product of 3TB-3CN, then with chromatographic column crude product is carried out separating-purifying, namely obtains the pure products of 3TB-3CN.
Each step reaction of 3TB-2CHO and 3TB-3CN is all carried out in microwave reactor.
For 3TB-2CHO, the washing fluid that chromatographic separation adopts is toluene; For 3TB-3CN, the washing fluid that chromatographic separation adopts is the mixed solvent of methylene dichloride and sherwood oil.
The structural characterization data of 3TB-3CN are as follows:
Mass spectrum: m/z 400.6 (M+);
Proton nmr spectra: δ (ppm): 7.98 (s, 3H), 7.71 (d, 3H), 7.26 (d, 3H);
Infrared spectra: (KBr method, cm
-1): 2265 (ν
C ≡ N).
3), the preparation of organic electrochromic device
The first step, the method for employing vacuum plating, at electroconductive ITO glass surface evaporation star-shaped oligothiophene derivative film, its thickness is 115nm;
Second step, take the perchloric acid 4-butyl amine as ionogen, acetonitrile is solvent, is mixed with electrolyte solution;
The 3rd step, having the electroconductive ITO glass of star-shaped oligothiophene derivative film and colourless transparent glass to be assembled into thickness with evaporation is 1.3 millimeters electrolyzer, in groove, add the electrolyte solution of preparing, insert simultaneously diameter and be 0.7 millimeter platinum line, respectively with electroconductive ITO glass and platinum line as electrode, be packaged into the organic electrochromic device;
The 4th step, when apply+when 2.5 V and-2.5 V voltage, in the device, the 3TB-2CHO film can occur faint yellow and russet reversible change; When apply+when 1.9 V and-1.9 V voltage, in the device, the 3TB-3CN film can occur faint yellow and orange-red reversible change.
Embodiment 3
1), the preparation of 3TB-2CHO:
The first step under the protection of nitrogen, adds in there-necked flask
N,
N-dimethyl formamide slowly drips phosphorus oxychloride, 65 ℃ of control temperature of reaction, and stirring reaction obtained reaction solution in 20 minutes;
Second step adds 1,3,5-three (2 in above-mentioned reaction solution
'-thienyl)-and benzene, stirring reaction obtained reaction soln in 35 minutes;
The 3rd step after reaction finishes, added the distilled water hydrolysis in the reaction soln of second step gained, obtain flocks, and vacuum filtration goes out flocks, is the crude product of 3TB-2CHO, then separates with chromatographic column, obtains the pure products of pure 3TB-2CHO.
The structural characterization data of 3TB-2CHO are as follows:
Mass spectrum: m/z 380.9 (M+);
Proton nmr spectra: δ (ppm): 9.96 (s, 2H), 8.15 ~ 8.05 (m, 4H), 8.03 (s, 3H), 7.85 (d, 1H), 7.71 (d, 1H), 7.25 (t, 1H);
Infrared spectra: (KBr method, cm
-1): 1650 (ν
C=O).
2), the preparation of 3TB-3CN:
The first step under the protection of nitrogen, adds 1,3,5-three (2 in there-necked flask
'-thienyl)-and benzene and methylene chloride, slowly drip Sulfuryl chloride isocyanate, 65 ℃ of control temperature of reaction, stirring reaction 20 minutes obtains reaction solution;
Second step adds in above-mentioned reaction solution
N,
N-dimethyl formamide, stirring reaction 25 minutes obtains reaction soln;
The 3rd step, after reaction finishes, in the resulting reaction soln of second step, add the distilled water hydrolysis, with the organic layer anhydrous sodium sulfate drying behind the dichloromethane extraction, get filtrate after removing by filter sodium sulfate, behind the methylene dichloride in the pressure reducing and steaming filtrate, namely obtain the crude product of 3TB-3CN, then separate with chromatographic column, namely obtain the pure products of 3TB-3CN.
Each step reaction of 3TB-2CHO and 3TB-3CN is all carried out in microwave reactor.
For 3TB-2CHO, the washing fluid that chromatographic separation adopts is toluene; For 3TB-3CN, the washing fluid that chromatographic separation adopts is the mixed solvent of methylene dichloride and sherwood oil.
The structural characterization data of 3TB-3CN are as follows:
Mass spectrum: m/z 400.6 (M+);
Proton nmr spectra: δ (ppm): 7.98 (s, 3H), 7.71 (d, 3H), 7.26 (d, 3H);
Infrared spectra: (KBr method, cm
-1): 2265 (ν
C ≡ N).
3), the preparation of organic electrochromic device
The first step, the method for employing vacuum plating, at electroconductive ITO glass surface evaporation star-shaped oligothiophene derivative film, its thickness is 130nm.
Second step, take the perchloric acid 4-butyl amine as ionogen, acetonitrile is solvent, is mixed with electrolyte solution.
The 3rd step, having the electroconductive ITO glass of star-shaped oligothiophene derivative film and colourless transparent glass to be assembled into thickness with evaporation is 1.5 millimeters electrolyzer, in groove, add the electrolyte solution of preparing, insert simultaneously diameter and be 0.8 millimeter platinum line, respectively with electroconductive ITO glass and platinum line as electrode, be packaged into the organic electrochromic device;
The 4th step, when apply+when 2.5 V and-2.5 V voltage, in the device, the 3TB-2CHO film can occur faint yellow and russet reversible change; When apply+when 1.9 V and-1.9 V voltage, in the device, the 3TB-3CN film can occur faint yellow and orange-red reversible change.
Claims (3)
1. the preparation method of star-shaped oligothiophene derivative, this star-shaped oligothiophene derivative is 1,3,5-three (2
'-(5
'-cyano group)-thienyl)-benzene, have following molecular structure:
(1) under the nitrogen protection, with 1,3,5-three (2
'-thienyl)-and benzene and methylene chloride mixing, get mixed solution; Slowly drip Sulfuryl chloride isocyanate in mixed solution, 30 ℃～65 ℃ of control temperature of reaction stirring reaction 40-60 minute, obtain reaction solution;
(2) add in the reaction solution that obtains to step (1)
N,
N-dimethyl formamide, stirring reaction 15 minutes～25 minutes obtains reaction soln;
(3) add the distilled water hydrolysis in the reaction soln that obtains to step (2), obtain hydrolyzed solution; Use the dichloromethane extraction hydrolyzed solution, the organic layer anhydrous sodium sulfate drying after the extraction, remove by filter sodium sulfate after, get filtrate; Behind the methylene dichloride in the pressure reducing and steaming filtrate, obtain 1,3,5-three (2
'-(5
'-cyano group)-thienyl)-crude product of benzene, crude product separates with chromatographic column, namely obtains purely 1,3, and 5-three (2
'-(5
'-cyano group)-thienyl)-benzene.
2. method according to claim 1 is characterized in that it is the mixed solvent of methylene dichloride and sherwood oil that described chromatographic column is separated the washing fluid that adopts.
3. preparation method according to claim 2 is characterized in that each step of described preparation all carries out in microwave reactor.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110192065 CN102329299B (en) | 2011-07-11 | 2011-07-11 | Star-shaped oligothiophene derivative, preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201110192065 CN102329299B (en) | 2011-07-11 | 2011-07-11 | Star-shaped oligothiophene derivative, preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN102329299A CN102329299A (en) | 2012-01-25 |
| CN102329299B true CN102329299B (en) | 2013-10-30 |
Family
ID=45481286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 201110192065 Active CN102329299B (en) | 2011-07-11 | 2011-07-11 | Star-shaped oligothiophene derivative, preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102329299B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103374022B (en) * | 2013-07-02 | 2016-01-06 | 华南理工大学 | Oligopoly thiophene derivative and preparation method thereof |
| CN109020948A (en) * | 2018-08-03 | 2018-12-18 | 浙江工业大学 | A kind of benzene-bigeminy thiophene derivant and the preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1730478A (en) * | 2005-08-30 | 2006-02-08 | 华南理工大学 | Uniformpoly thiophene derivative and its preparation method and uses |
| CN101367790A (en) * | 2008-09-19 | 2009-02-18 | 华南理工大学 | Quick preparation method for oligomerization thiophene derivant and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7247735B2 (en) * | 2002-07-26 | 2007-07-24 | Infineon Technologies Ag | Octupolar molecules used as organic semiconductors |
-
2011
- 2011-07-11 CN CN 201110192065 patent/CN102329299B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1730478A (en) * | 2005-08-30 | 2006-02-08 | 华南理工大学 | Uniformpoly thiophene derivative and its preparation method and uses |
| CN101367790A (en) * | 2008-09-19 | 2009-02-18 | 华南理工大学 | Quick preparation method for oligomerization thiophene derivant and uses thereof |
Non-Patent Citations (4)
| Title |
|---|
| 1,3,5-Tris(2-acetylthienyl)benzene;Chen-Hao Zhu, et.al.;《Acta Crystallographica Section E Structure Reports Online》;20061231;第E62卷;第o4312–o4314页 * |
| Chen-Hao Zhu, et.al..1,3,5-Tris(2-acetylthienyl)benzene.《Acta Crystallographica Section E Structure Reports Online》.2006,第E62卷第o4312–o4314页. |
| Frederic Cherioux, et.al..Synthesis and Electrochemical Properties of Novel 1,3,5-Tris(oligothienyl)benzenes: A New Generation of 3D Reticulating Agents.《Adv. Funct. Mater.》.2001,第11卷(第4期),第305-309页. |
| Synthesis and Electrochemical Properties of Novel 1,3,5-Tris(oligothienyl)benzenes: A New Generation of 3D Reticulating Agents;Frederic Cherioux, et.al.;《Adv. Funct. Mater.》;20010831;第11卷(第4期);第305-309页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN102329299A (en) | 2012-01-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3013840B1 (en) | Electrochromic compound, electrochromic composition, display element, and dimming element | |
| Ming et al. | Chalcogenodiazolo [3, 4-c] pyridine based donor–acceptor–donor polymers for green and near-infrared electrochromics | |
| KR101897386B1 (en) | Electrochromic compound, electrochromic composition, display element, and dimming element | |
| EP2914608B1 (en) | Electrochromic compound, electrochromic composition, and display element | |
| CN114685469B (en) | Thiophene derivative based on 9-phenyl-carbazole and preparation and application thereof | |
| CN114907551B (en) | Red electrochromic polymer, preparation method, film and device | |
| Huang et al. | Photoactively electroactive polyamide with azo group in the main chain via oxidative coupling polymerization | |
| Mantione et al. | Easy‐to‐make carboxylic acid dioxythiophene monomer (ProDOT‐COOH) and functional conductive polymers | |
| Halder et al. | Vis-to-NIR electrochromism and bright-to-dark electrofluorochromism in a triazine and thiophene-based three-dimensional covalent polymer | |
| CN102329299B (en) | Star-shaped oligothiophene derivative, preparation method and application thereof | |
| CN114853988A (en) | Electrochromic polymer containing thiophene embedded unit, preparation method, thin film and device | |
| CN110713493B (en) | Electrochemical polymerization preparation and application of triphenylamine derivative conjugated polymer material | |
| CN103554505B (en) | Terpyridyl-fluorenes metal hybrid polymkeric substance and the electrochromic device containing this polymkeric substance | |
| CN108997427B (en) | Electrochromic compound, application, electrochromic device prepared from electrochromic compound and application | |
| CN116874747A (en) | Electrochromic polymer, preparation method thereof and electrochromic polymer film | |
| Qian et al. | The influence of pendent anions on electrochemical and electrochromic properties of thiophene-triphenylamine-based polymeric ionic liquids | |
| Shi et al. | Solution-processable low-bandgap 3-fluorothieno [3, 4-b] thiophene-2-carboxylate-based conjugated polymers for electrochromic applications | |
| Winkel et al. | Synthesis and electropolymerization of 3, 5-bis-(3, 4-ethylenedioxythien-2-yl)-4, 4-dimethyl isopyrazole: a donor-acceptor-donor monomer | |
| Liu et al. | Novel terpyridine-Fe (II) coordination polymers with zigzag configuration for efficient electrochromic energy storage devices | |
| CN103193793A (en) | Salicylic acid functionalized (3, 4-ethylenedioxythiophene) monomer, polymer and preparation methods thereof | |
| CN109053675A (en) | A kind of benzene-methyl-bigeminy thiophene derivant and the preparation method and application thereof | |
| CN110606939A (en) | Application and preparation of poly (N, N-diphenyl-4- (2, 5-dimethyl-1H-pyrrole-1-yl) aniline) | |
| Guan et al. | Synthesis and Electrochromic Properties Based on Star-shaped Oligothiophene Derivatives with Phenyl Core | |
| CN118684865A (en) | Electrochromic polymer of triphenylamine derivative and preparation method and application thereof | |
| Qu et al. | Synthesis and optoelectronic properties of free-standing polythiophene cross-linking polycarbazole films |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20161207 Address after: 519030 Guangdong city of Zhuhai province Hengqin Baohua Road No. 6, room 105 -15480 Patentee after: Zhuhai Shang Ming optoelectronics Co., Ltd. Address before: 510640 Tianhe District, Guangdong, No. five road, No. 381, Patentee before: South China University of Technology |