Local dense quaternized polyfluorene ether ketone compound and preparation method thereof

A ketone compound and polyfluorene ether technology, which is applied in the field of local intensive quaternization of polyfluorene ether ketone compounds and their preparation, can solve the problem that the chloromethylation reagent is highly toxic and cannot precisely control the position where the quaternary ammonium salt cation is connected. and quantity, etc., to achieve the effect of low price, excellent solubility, and easy availability

Inactive Publication Date: 2018-09-14
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method cannot precisely control the location and quantity of quaternary ammonium salt cations, and chloromethylation reagents are generally highly toxic

Method used

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  • Local dense quaternized polyfluorene ether ketone compound and preparation method thereof
  • Local dense quaternized polyfluorene ether ketone compound and preparation method thereof
  • Local dense quaternized polyfluorene ether ketone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1 Preparation of compound I containing eight benzyl groups

[0045]25.00 g (61.5 mmol) 9,9-bis(3,5-dimethyl-4-hydroxyphenyl) fluorene, 33.84 g (157.3 mmol) 4-bromo-2,6-dimethylanisole, Add 34.04 g (246.5 mmol) of anhydrous potassium carbonate, 5.83 g (40.6 mmol) of cuprous bromide, 21 mL (270.4 mmol) of pyridine, and 300 mL of N,N-dimethylformamide into a 500 mL three-necked flask, Under the protection of argon, stir magnetically at 165°C for 170 hours, then acidify the product to pH 2, filter, extract with water and dichloromethane, and finally purify by chromatography to obtain eight benzyl compounds I. Yield: 29.1%. The data of the proton nuclear magnetic resonance spectrum of this compound are: 1 H NMR (400 MHz, CDCl 3 , ppm)δ 2.05 (s, 12H),2.22 (s, 12H), 3.69 (s, 6H), 6.40 (s, 4H), 6.94 (s, 4H), 7.36 (t, 2H), 7.43(t, 2H), 7.55 (d, 2H), 7.83 (d, 2H).

Embodiment 2

[0046] Example 2 Preparation of bisphenol monomer II containing eight benzyl groups

[0047] Add 5.17 g (7.66 mmol) of compound I containing eight benzyl groups in Example 1, and 130 mL of dichloromethane into a 250 mL three-necked round-bottomed flask, and use liquid nitrogen and acetone to bring the temperature of the system under the protection of argon. The temperature was lowered to -78°C, and 4.66 g (18.5 mmol) of boron tribromide was slowly added, and then the reaction was continued at room temperature for 10 hours. After the reaction, the product was poured into 200 mL of deionized water, extracted with water and methylene chloride, and purified by chromatography to obtain bisphenol monomer II containing eight benzyl groups. Yield: 99%. The data of the proton nuclear magnetic resonance spectrum of this compound are: 1 H NMR (400 MHz, CDCl 3 ,ppm) δ 2.05 (s, 12H), 2.19 (s, 12H), 4.32 (s, 2H), 6.39 (s, 4H), 6.93 (s,4H), 7.36 (t, 2H), 7.43 (t, 2H), 7.56 (d, 2H), 7.83 ...

Embodiment 3

[0048] Example 3 Preparation of polyfluorene ether ketone compound A containing benzyl

[0049] The bisphenol monomer II containing eight benzyl groups in Example 2 0.3881 g (0.6 mmol), 0.8410 g (2.4 mmol) 9,9-bis (4-hydroxyphenyl) fluorene, 0.6546 g (3 mmol) Add 4,4'-difluorobenzophenone, 0.6219 g (4.5 mmol) of anhydrous potassium carbonate, 6 mL of toluene and 10 mL of N,N-dimethylacetamide into a 25 mL three-necked flask under argon atmosphere Under protection, the temperature was raised to 145°C for 2 hours, and then the temperature was raised to 165°C to continue the reaction for 15 hours. After the reaction, the product was poured into deionized water to precipitate a precipitate, and the precipitate was collected by filtration and redissolved in dichloromethane, and then poured The precipitate was precipitated in methanol, and the precipitate was collected by filtration and dried in a vacuum oven at 80°C for 24 hours to obtain the polyfluorene ether ketone compound A co...

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Abstract

The invention relates to a local dense quaternized polyfluorene ether ketone compound and a preparation method thereof. A novel bisphenol monomer containing eight benzyls and flourenyls is firstly designed; then, the monomer, and different proportions of 9,9-bi(4-hydroxy phenyl)fluorine and 4,4'-difluorobenzophenone take condensation polymerization reaction to prepare a polyfluorene ether ketone compound containing benzyl; through N-bromo-succinimide, the benzyl is converted into bromomethyl; further, through trimethylamine, the bromomethyl is converted into quaternary ammonium salt groups; aseries of local dense quaternized polyfluorene ether ketone compounds is prepared. The series compound has good solubility in polar aprotic solvents such as N,N-dimethylacetamide, N,N-dimethylformamide, N-methyl pyrrolidone and dimethyl sulfoxide; the compound can be cast into a membrane by a solution; a prepared anion exchange membrane has the characteristics of high heat stability, high oxidation stability, high anion conductivity, good mechanical property and the like.

Description

technical field [0001] The invention relates to a locally intensive quaternized polyfluorene ether ketone compound and a preparation method thereof, belonging to the field of ion exchange membrane materials. Background technique [0002] Anion exchange membranes have important applications in many fields such as fuel cells, liquid flow batteries, electrodialysis, and water electrolysis, so they have received extensive attention. An ideal anion exchange membrane should have the characteristics of simple preparation process, low cost, high anion conductivity, and good mechanical and chemical stability. At present, the application of anion exchange membranes mainly has the problem of low ion conductivity, and the ion conductivity mainly depends on the content and microscopic morphology of cationic groups. The ion conductivity can be improved by increasing the content of ionic groups in the anion exchange membrane, but this will lead to high water absorption of the membrane and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J5/22C08G65/48C08G65/40C08L71/10
Inventor 陈栋阳陈煜
Owner FUZHOU UNIV
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