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Thiophene derivative based on 9-phenyl-carbazole as well as preparation and application of thiophene derivative

A technology of tributylstannyl dithiophene and its derivatives, applied in organic chemistry, chemical instruments and methods, color-changing fluorescent materials, etc., can solve the problem of high driving voltage, achieve increased conjugation degree, great application value, The effect of lowering the redox potential

Pending Publication Date: 2022-07-01
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are relatively few studies on the electrochromic properties of pure polythiophene, because the electrochemical polymerization potential of pure polythiophene is relatively high, so the driving voltage required for its color change is relatively high

Method used

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  • Thiophene derivative based on 9-phenyl-carbazole as well as preparation and application of thiophene derivative
  • Thiophene derivative based on 9-phenyl-carbazole as well as preparation and application of thiophene derivative
  • Thiophene derivative based on 9-phenyl-carbazole as well as preparation and application of thiophene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Synthesis of TBTCB-3Br

[0030] Combine 9-(4-bromophenyl)-carbazole (0.5 g, 1.55 mmol), N-bromosuccinimide (1.65 g, 6.2 mmol) and N,N-dimethylformamide (30 mL) ) into a single-necked round-bottomed flask in turn, and stirred at 0 °C in an ice-water mixed bath for 8 hours. After the reaction was completed, pour the fully reacted solution into 200 mL of deionized water, and extract 5 times with 400 mL of dichloromethane. , until the solvent N, N-dimethylformamide was completely extracted, the extract was concentrated, dried with anhydrous sodium sulfate to remove water, mixed with crude silica gel (Qingdao Yumingyuan Silica Reagent Co., Ltd.), and then subjected to column chromatography Purification, using fine silica gel (Qingdao Yumingyuan Silica Reagent Co., Ltd.) as the stationary phase, dichloromethane and petroleum ether with a volume ratio of 1:4~5 as the mobile phase, collecting the eluent containing the target compound, and removing it by rotary evapor...

Embodiment 2

[0032] Example 2: Synthesis of Thiophene Derivatives of 9-Phenyl-carbazole (TBTCB-3T)

[0033] The TBTCB-3Br (0.8 g, 1.68 mmol) prepared in Example 1 and an appropriate amount of bis(triphenylphosphine) palladium dichloride were added to a 100 mL two-necked round-bottomed flask, and the mixture was heated under N 2 Under protection, 20 mL of N,N-dimethylformamide and 2-tributylstannyl dithiophene (6.86 g, 15.12 mmol) were added to the reaction flask in turn, stirred, and heated to reflux at 120 °C for 36 hours. After the reaction was completed, pour the completed solution into 200 mL of deionized water, and extract with 400 mL of dichloromethane for 5 times until the solvent N,N-dimethylformamide was completely extracted. After drying with sodium sulfate to remove water, the sample was mixed with crude silica gel, and then purified by column chromatography. Using fine silica gel as the stationary phase and dichloromethane and petroleum ether as the mobile phases, the eluate co...

Embodiment 3

[0035] Example 3: Preparation of polymer films of thiophene derivatives of 9-phenyl-carbazole

[0036] The thiophene derivatives of 9-phenyl-carbazole (TBTCB-3T) 7.35 mg (1 mmol / L) and the electrolyte tetrabutylammonium hexafluorophosphate 0.387 g (0.1 mol / L) were added to a 10 mL volumetric flask , dilute to volume with chromatographic grade dichloromethane, ultrasonicate for 3 min, and after the solid is completely dissolved, carry out electrochemical polymerization, and the polymerization curve is as follows Figure 4 shown. With ITO glass (0.9 4cm) is the working electrode, the platinum sheet is the counter electrode, and the Ag / AgCl is the reference electrode. The pTBTCB-3T polymer film was obtained by cyclic voltammetry polymerization. The polymerization voltage ranged from 0 to 1.5 V. 6 laps. Dedoping in a blank electrolyte solution (0.387 g tetrabutylammonium hexafluorophosphate, make up to 10 mL with chromatography grade dichloromethane) at a dedoping voltage of -0....

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Abstract

The invention provides a 9-phenyl-carbazole-based thiophene derivative as shown in a formula (I) as well as preparation and application of the 9-phenyl-carbazole-based thiophene derivative. According to the thiophene derivative based on 9-phenyl-carbazole, thiophene is used as a peripheral group, 9-phenyl-carbazole is used as a central core, compared with a thiophene monomer, the thiophene derivative based on 9-phenyl-carbazole shows a larger conjugate length, and the redox potential of thiophene is greatly reduced, so that a corresponding polymer film is obtained through electrochemical polymerization; the reversible color change from bright yellow to blue can be realized under different voltages, the good electrochromic performance is shown, and the huge application prospect is shown in the fields of electronic tags and electronic paper.

Description

technical field [0001] The present invention relates to a thiophene derivative based on 9-phenyl-carbazole, a preparation method thereof, and its application in preparing electrochromic materials. Background technique [0002] Electrochromism refers to the phenomenon that certain materials reversibly change their color and optical properties through redox reactions under an applied electric field. It has been used in smart windows, automotive rearview mirrors and other fields. Conductive polymer materials have received extensive attention in the field of electrochromism due to their wide color change range, high optical contrast, fast response speed, and controllable energy band. Thiophene is a five-membered heterocyclic structure, and polythiophene-based conductive polymers have the characteristics of easy synthesis, cheap raw materials, etc., and because of their good environmental stability and thermal stability during doping and de-doping, they have become a research top...

Claims

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Application Information

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IPC IPC(8): C07D409/14C09K9/02
CPCC07D409/14C09K9/02C09K2211/1029C09K2211/1092
Inventor 邵明发张诚吕晓静
Owner ZHEJIANG UNIV OF TECH
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