Quinacridone-thiophene derivative, preparation method and application thereof

A technology of thiophene derivatives and quinacridone, which is applied in the field of quinacridone-thiophene derivatives and its preparation, can solve the problems of slow response speed, limited application range, single color display, etc., and achieve good electrochemical cycle stability sexual effect

Pending Publication Date: 2020-12-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Early electrochromic materials were mainly inorganic electrochromic materials, including transition metal oxides, but their slow response speed, single color display and low coloring efficiency severely limited their application range

Method used

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  • Quinacridone-thiophene derivative, preparation method and application thereof
  • Quinacridone-thiophene derivative, preparation method and application thereof
  • Quinacridone-thiophene derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Synthesis of C10QA

[0049]

[0050] Quinacridone 3.12g (0.01mol), 1-bromodecane 8.84g (0.04mol), sodium hydroxide 1.6g (0.04mol), tetrabutylammonium bromide 1.3g (0.004mol), dimethyl ethylene Add 30mL of sulfone to a 100mL single-necked flask in sequence, and stir at room temperature for 24 hours. After the reaction, extract with water and dichloromethane three times. After the extract is concentrated, use anhydrous sodium sulfate to remove water, and perform column chromatography purification, using silica gel as the stationary phase. Dichloromethane and petroleum ether were used as the mobile phase. The eluate containing the target compound was collected, and the solvent was removed by rotary evaporation and dried to obtain orange-red solid C10QA with a yield of 85%. The characterization structure of the confirmed substance is as follows: 1 HNMR (500MHz, CDCl 3 )δ 8.82(s, 2H), 8.61(dd, 2H), 7.80(td, 2H), 7.56(d, 2H), 7.30(t, 2H), 4.55(m, 4H), 2.0(m, 4...

Embodiment 2

[0051] Example 2: Synthesis of C10QA-2Br

[0052]Add 1.19g (0.002mol) of C10QA and 1.25g (0.007mol) of NBS into a 100mL two-necked flask, add 10mL of N,N-dimethylformamide (DMF) under nitrogen protection, heat to reflux, and react in the dark for 24 hours , after the reaction, extract three times with water and dichloromethane, concentrate the extract and remove water with anhydrous sodium sulfate, carry out column chromatography purification, use silica gel as the stationary phase, dichloromethane and petroleum ether as the mobile phase, collect the The eluate of the compound was evaporated to remove the solvent and dried to obtain orange-red solid C10QA-2Br with a yield of 80%. The characterization structure of the confirmed substance is as follows: 1 H NMR (500MHz, CDCl 3 )δ8.78(s, 2H), 8.70(s, 2H), 7.85(d, 2H), 7.45(d, 2H), 4.55(m, 4H), 2.0(m, 4H), 1.64(m, 4H ), 1.47(m, 4H), 1.42-1.20(m, 20H), 0.90(t, 6H).

Embodiment 3

[0053] Example 3: Synthesis of C10QA-2T

[0054] Add 0.32g (0.4mmol) of C10QA-2Br and a small amount of tetrakis(triphenylphosphine)palladium to a 100mL two-necked flask, and add 0.64g (0.16mmol) of 2-tributylstannylthiophene and 10mL of DMF under nitrogen protection. , heated to reflux for 12 hours. After the reaction, extract three times with water and dichloromethane, concentrate the extract, remove water with anhydrous sodium sulfate, and perform column chromatography purification, using silica gel as the stationary phase, dichloromethane and petroleum ether as the mobile phase, and collect the target compound. The eluate was evaporated to remove the solvent and dried to obtain pink solid C10QA-2T with a yield of 60%. The characterization structure of the confirmed substance is as follows: 1 H NMR (500MHz, CDCl 3 )δ 8.77(s, 2H), 8.69(s, 2H), 7.85(d, J=9.2Hz, 2H), 7.45(d, J=8.4 Hz, 2H), 4.52(s, 4H), 2.24(m , 4H), 1.60 (m, 4H), 1.52-1.20 (m, 24H), 0.90 (t, 6H).

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Abstract

The invention discloses a quinacridone-thiophene derivative shown as formula (I), a preparation method and application thereof in the field of electrochromism. The quinacridone-thiophene derivative has a rigid planar structure, the thiophene group has excellent electrochemical activity, a polymer film can be prepared through electrochemical polymerization, the film can realize reversible color change from orange red to blue black under the step voltage of 0-1.2V, the coloring time at 444nm, 658nm and 1100nm is respectively 3.60s, 2.04s and 3.55s, and the fading time is respectively 0.79s, 0.68s and 0.92s. The film is almost not attenuated in terms of contrast after 100 cycles under the wavelength of 658nm, and shows good electrochemical cycle stability, thus indicating that the quinacridone-thiophene derivative has a potential application prospect in the field of electrochromism.

Description

[0001] (1) Technical field [0002] The invention relates to a quinacridone-thiophene derivative with quinacridone as the central core and thiophene as the peripheral group, a preparation method thereof, and an application thereof in the field of electrochromism. [0003] (2) Background technology [0004] Quinacridone compounds are a kind of easy-to-obtain organic pigments, the hue is mainly red and purple, the molecular planarity is good, and the fastness is excellent, especially the light fastness and heat fastness are the best. The heat is close to 300°C, so it is widely used in high-grade coatings, engineering plastics, inks, fiber puree coloring and other fields, but the solubility of quinacridone compounds is extremely poor, thus limiting its application in other fields. Later, it was found that substituting long alkyl chains at its N position can effectively adjust the solubility and photoelectric properties of quinacridone derivatives in solvents. [0005] Electrochro...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K9/02C08J5/18C08L65/00
CPCC07D471/04C09K9/02C08J5/18C09K2211/1044C09K2211/1092C08J2365/00Y02E10/549
Inventor 吕晓静李锦张诚杨园园张凌
Owner ZHEJIANG UNIV OF TECH
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