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Bidiindoledione d-a-d type polymer electrochromic material and preparation method thereof

An electrochromic material, D-A-D technology, applied in the direction of color-changing fluorescent materials, chemical instruments and methods, etc., can solve the problems of increasing the difficulty of polymerization and restricting the development of polymers in the field of electrochromism, achieving a wide light absorption range and wide application range Effect

Inactive Publication Date: 2018-11-06
JIANGXI SCI & TECH NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, in the family of donor-acceptor electrochromic polymers, the research on the donor unit is relatively mature, but the weak electron cloud density of the acceptor unit increases the difficulty of polymerization, which limits the use of corresponding polymers in electrochromic polymers. field development

Method used

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  • Bidiindoledione d-a-d type polymer electrochromic material and preparation method thereof
  • Bidiindoledione d-a-d type polymer electrochromic material and preparation method thereof
  • Bidiindoledione d-a-d type polymer electrochromic material and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1: the electrochemical synthesis of P (IDOH-EDOT) polymer electrochromic material

[0060] (1) Synthesis of IDOH-EDOT active precursor

[0061]

[0062] Under the condition of nitrogen protection, add a certain proportion of 6,6'-dibromo-3,3'-dihexylindoledione, 2-tinbutyl-3,4-ethane into a three-necked flask filled with toluene solvent Dioxythiophene, in catalyst Pd(PPh 3 ) 4 Under catalysis, it was condensed and refluxed at 110°C for 12 hours; after the reaction, the product was extracted three times with chloroform, dried with a small amount of anhydrous magnesium sulfate for 24 hours, and then the solvent was distilled off under reduced pressure, separated by silica gel chromatography, and purified to obtain a purple-red solid product , the yield was 80%. 1 HNMR (CDCl 3 ): δ9.14(d,J=8.47Hz,2H),7.35–7.33(dd,J 1 =8.4Hz, J2=1.6Hz, 2H), 7.22(s, 2H), 6.39(s, 2H), 4.36–4.28(m, 8H), 3.82–3.79(m, 4H), 1.65-1.55(m, 4H), 1.43–1.24(m,12H), 0.98–0.86(m,6H). ...

Embodiment 2

[0073] Embodiment 2: the electrochemical synthesis of P (IDOD-EDOT) polymer electrochromic material

[0074] (1) Synthesis of IDOD-EDOT active precursor

[0075]

[0076] Under the condition of nitrogen protection, a certain proportion of 6,6'-dibromo-3,3'-bidocosindoledione, 2-tinbutyl-3,4 -Ethylenedioxythiophene, in catalyst Pd(PPh 3 ) 4 Under catalysis, it was condensed and refluxed at 110°C for 12 hours; after the reaction, the product was extracted three times with chloroform, dried with a small amount of anhydrous magnesium sulfate for 24 hours, and then the solvent was distilled off under reduced pressure, separated by silica gel chromatography, and purified to obtain a purple-red solid product , the yield was 88%. 1 HNMR (CDCl 3 ): δ9.01(d,J=8.47Hz,2H),7.35–7.33(dd,J 1 =8.4Hz,J 2 =1.6Hz,2H),7.22(s,2H),6.39(s,2H),4.36–4.28(m,8H),3.8–3.7(m,4H),1.65-1.55(m,4H),1.43– 1.24(m,36H),0.98–0.86(m,6H).

[0077] (2) Electrochemical polymerization of P(IDOD-EDOT) polymer...

Embodiment 3

[0086] Embodiment 3: Electrochemical synthesis of P (IDOH-Th) polymer electrochromic material

[0087] (1) Synthesis of IDOH-Th active precursor

[0088]

[0089] Under nitrogen protection conditions, a certain proportion of 6,6'-dibromo-3,3'-dihexylindoledione and 2-tinbutylthiophene were added to a three-necked flask filled with toluene solvent, and the catalyst Pd( PPh 3 ) 2 Cl 2 Under catalysis, it was condensed and refluxed at 110°C for 12 hours; after the reaction, the product was extracted three times with chloroform, dried with a small amount of anhydrous magnesium sulfate for 24 hours, and then the solvent was distilled off under reduced pressure, separated by silica gel chromatography, and purified to obtain a reddish-brown solid product , the yield was 65%. 1 H-NMR (CDCl 3 ): δ9.14(d,J=8.47Hz,2H),7.35–7.33(dd,J 1 =8.4Hz,J 2 =1.6Hz,2H),7.22(s,2H),6.39(s,2H),4.36–4.28(m,8H),3.8–3.7(m,4H),1.65-1.55(m,4H),1.43– 1.24(m,12H),0.98–0.86(m,6H).(eg Figure 9 shown...

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Abstract

The invention discloses a bi-diindoledione D-A-D polymer electrochromic material and a preparation method thereof, belonging to the field of polymer electrochromic materials, wherein the bi-diindole diketone monomer The structure is acceptor (A), and furyl, selenyl, thienyl and their derivatives, pyrrolyl and their derivatives are donors (D); polymer electrochromic is obtained by electrochemical polymerization from active precursors Materials or polymer electrochromic materials can be obtained by one-step polymerization reaction by chemical method. Due to the presence of N atoms and diketone functional groups in the structure of the polymer electrochromic material, the diindolyl diketones have a strong electron-withdrawing ability as the acceptor structure, which makes the polymer electrochromic material It has lower bandwidth, wider light absorption range, and has the characteristics of richer colors, faster response time, higher coloring efficiency, and better stability.

Description

technical field [0001] The invention relates to the field of polymer electrochromic materials, in particular to a class of biindoledione D-A-D polymer electrochromic materials and a preparation method thereof, using biindolediketones as acceptors (A) , Furanyl, selenophene, thienyl and its thienyl derivatives, pyrrolyl and its pyrrolyl derivatives as the donor (D) D-A-D type polymer electrochromic materials and device performance research. Background technique [0002] Electrochromism refers to the phenomenon that the optical properties of materials (mainly reflectivity, transmittance, absorption rate, etc.) undergo reversible color changes under the action of an external electric field, and appear as reversible changes in color and transparency in appearance. Electrochromic materials can be applied to light-weight and portable display devices such as electronic paper, devices using light transmittance such as smart windows, and the like. At present, the core issue in the f...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C09K9/02
CPCC08G61/122C08G61/124C08G61/126C08G2261/124C08G2261/1414C08G2261/3223C08G2261/344C08G2261/411C08G2261/414C08G2261/54C08G2261/90C09K9/02C09K2211/1466
Inventor 徐景坤顾华卢宝阳陈帅明守利林凯文刘宏涛
Owner JIANGXI SCI & TECH NORMAL UNIV
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