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Electrochemical polymerization preparation of triphenylamine derivative conjugated polymer material and applications

An electrochemical and polymer thin film technology, applied in the fields of organic chemistry, color-changing fluorescent materials, chemical instruments and methods, etc., can solve the problems of limiting the application of electrochromic field, difficult to prepare by electrochemical polymerization, etc.

Active Publication Date: 2020-01-21
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its triphenylamine dimer will form a very stable delocalization phenomenon in the oxidation-reduction process, which makes it difficult to further prepare by electrochemical polymerization, thus limiting its application in the field of electrochromism

Method used

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  • Electrochemical polymerization preparation of triphenylamine derivative conjugated polymer material and applications
  • Electrochemical polymerization preparation of triphenylamine derivative conjugated polymer material and applications
  • Electrochemical polymerization preparation of triphenylamine derivative conjugated polymer material and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Embodiment 1: Synthesis of 2,3,8,9,14,15-six (4-dianilinophenyl)-hexaazyridine:

[0065] Add hexahydrate and cyclohexanone (60mg), 4,5-bis(N,N-diphenylbenzene)-1,2-diaminobenzene (600mg) into a pre-washed and dried 50ml two-necked flask, nitrogen protection Then add glacial acetic acid (20ml), heat up to 120°C, and react for 15h. After the reaction was completed, it was washed and extracted three times with dichloromethane and deionized water, and the organic phase was collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography. Using 200-300 mesh silica gel as the stationary phase, eluting with a dichloromethane / ethyl acetate mixture with a volume ratio of 2:1 as the mobile phase, collecting the eluate containing the target compound, distilling off the solvent under reduced pressure and drying to obtain Red solid 344mg, yield 85%. 1 H NMR (500MHz, CDCl3) δ8.73 (s, 6H), 7.34-7.28 (m,, 36H)...

Embodiment 2

[0066] Example 2: Synthesis of 4,5-bis(N,N-diphenylbenzene)-1,2-diaminobenzene:

[0067] Add 4-boric acid triphenylamine (773mg), 4,5-dibromo-o-diaminobenzene (138mg), Pd(PPh 3 ) 2 Cl 2 (40mg), K 2 CO 3 (424mg), after nitrogen protection, 30ml of toluene and 2ml of deionized water were added, the temperature was raised to 80°C, and the reaction was carried out for 24h. After the reaction, the mixture was washed and extracted with dichloromethane and water several times, and the organic phase was collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and separated and purified by column chromatography. Use 200-300 mesh silica gel as the stationary phase, and use dichloromethane / petroleum ether mixed solution with a volume ratio of 3:1 as the mobile phase for elution, collect the eluate containing the target compound, distill off the solvent under reduced pressure and dry it, then TLC was used to obtain 488 mg of pink solid with a yield of 8...

Embodiment 3

[0068] Example 3: Preparation and characterization of 2,3,8,9,14,15-hexa(4-dianilinophenyl)-hexaazyridine polymer film:

[0069] Characterization of 2,3,8,9,14,15-hexa(4-dianilinophenyl)-hexaazyridine monomer in polymer film by infrared spectroscopy (see attached image 3 ), it can be seen from the figure that the compound monomer and the polymer film have the characteristic infrared absorption peaks of the triphenylamine unit and the central core hexaazyridine at the same time. Located at 1594, 1515, 1452cm -1 The absorption peak is the skeleton vibration of substituted benzene, 1488cm -1 and 1360cm -1 The absorption peaks at are respectively the C=N stretching vibration and the C-N stretching vibration in the naphthalene heterocycle, 1273 and 1180cm -1 The absorption peak at corresponds to the C-N stretching vibration in triphenylamine and the C-H in-plane bending vibration of substituted benzene, 889 and 831 cm -1 Corresponding to 1,2,4 trisubstituted benzene C-H out-of...

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Abstract

The invention relates to a 2,3,8,9,14,15-hexa(4-diphenylaminophenyl)-hexa-aza-naphthalene (DTPA-HATN) organic small molecule having a triphenylamine-naphthalene heterocyclic structure and a preparation method thereof, and provides an electrochemical polymerization preparation method of a poly[2,3,8,9,14,15-hexa(4-diphenylaminophenyl)-hexa-aza-naphthalene] polymer film with high contrast (as most as 60%) and good cycling stability. The invention provides an application of the poly[2,3,8,9,14,15-hexa(4-diphenylaminophenyl)-hexa-aza-naphthalene] polymer film as an electrochromic material. According to the invention, electrochemical polymerization preparation is realized, and application in the field of electrochromism is realized.

Description

technical field [0001] The invention relates to a poly[2,3,8,9,14,15-hexa(4-dianilinophenyl)-hexaazyridine] conjugated polymer material and its monomer, preparation method and its use in Applications in the field of electrochromism. Background technique [0002] Electrochromism refers to the reversible conversion of the optical properties (absorption, transmittance, reflectance, etc.) Its macroscopic performance is the reversible conversion of the color of the material with the applied electric field. [0003] As a new energy-saving and environmentally friendly material, electrochromic materials are currently the most common applications including smart windows, anti-glare rearview mirrors, electronic paper and military camouflage materials. Electrochromic materials can be divided into two categories: inorganic and organic. Inorganic electrochromic materials are based on inorganic metal oxides (WO 3 , V 2 o 5 , Prussian blue system, etc.), has good photochemical stabili...

Claims

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Application Information

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IPC IPC(8): C07D487/14C25B3/10C09K9/02C25B3/29
CPCC07D487/14C09K9/02C09K2211/1466C09K2211/1433C25B3/29
Inventor 李维军徐宁陈章新张诚
Owner ZHEJIANG UNIV OF TECH
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