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Bis-indolinedione D-A-D type polymer electrochromic material and preparation method thereof

A technology of electrochromic materials and indoledione, which is applied in the direction of color-changing fluorescent materials, chemical instruments and methods, can solve the problems of increasing the difficulty of polymerization and limiting the development of polymers in the field of electrochromism, and achieves a wide light absorption range, Wide range of effects

Inactive Publication Date: 2016-12-21
JIANGXI SCI & TECH NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Bis-indolinedione D-A-D type polymer electrochromic material and preparation method thereof
  • Bis-indolinedione D-A-D type polymer electrochromic material and preparation method thereof
  • Bis-indolinedione D-A-D type polymer electrochromic material and preparation method thereof

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Experimental program
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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 bis-indolinedione D-A-D type polymer electrochromic material and a preparation method thereof, and belongs to the field of polymer electrochromic materials, wherein the bis-indolinedione monomer structure is as a receptor (A), donors (D) comprise furan group, selenophene group, thiophene group and derivatives thereof, and pyrrole group and derivatives thereof; and the polymer electrochromic material is obtained by electrochemical polymerization method or a chemical method from an active precursor. Due to N atoms and dione functional groups in the structure of the polymer electrochromic material, bis-indolinedione as the receptor structure has strong electron-withdrawing ability, so that the bis-indolinedione D-A-D type polymer electrochromic material has lower bandwidth, a wide light absorption range, richer color, faster response time, higher coloration efficiency, better stability and other characteristics.

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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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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