Fluorine-containing high dielectric polynorbornene-poly(1,6-heptadiyne) block copolymer and preparation method thereof

A technology of polynorbornene and block copolymer, which is applied in the field of high dielectric polymer preparation, can solve the problem that the related work of dielectric materials has not yet been reported, etc.

Inactive Publication Date: 2017-01-04
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Polyacetylene is the simplest conductive polymer, but the preparation of dielectric materials based on polyacetylene derivatives has not been reported yet

Method used

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  • Fluorine-containing high dielectric polynorbornene-poly(1,6-heptadiyne) block copolymer and preparation method thereof
  • Fluorine-containing high dielectric polynorbornene-poly(1,6-heptadiyne) block copolymer and preparation method thereof
  • Fluorine-containing high dielectric polynorbornene-poly(1,6-heptadiyne) block copolymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: Synthesis of N-3,5-difluorophenyl norbornenepyrrolidine

[0060] At room temperature, dissolve 3,6-endomethine-1,2,3,6-tetrahydrophthalic anhydride (9.84g, 60mmol) and 3,5-difluoroaniline (6.45g, 50mmol) in 50mL In anhydrous 1,2-dichloroethane. Nitrogen gas was introduced, and 0.3 equivalent of DMAP (1.83 g, 15 mmol) was added to the reaction solution. Reflux at 90°C for 36 hours, and the reaction is complete. After washing, drying, and solvent removal for many times, the crude product is recrystallized to obtain white crystals, which is a norborneneimide compound containing 3,5-difluorophenyl. Under an ice bath, nitrogen was introduced into the reaction flask, lithium aluminum hydride (4.56 g, 120 mmol) was quickly added into the flask, and 100 mL of anhydrous ether was injected to obtain a suspension of lithium aluminum hydride. Subsequently, the norbornenimide compound (6.7 g, 24 mmol) containing 3,5-difluorophenyl was dissolved in 80 mL of dry dichloromet...

Embodiment 2

[0062] Example 2: Synthesis of pentafluorophenyl 4-carboxylate-1,6-heptadiyne

[0063] At room temperature, add 4-carboxy-1.6-heptadiyne (3.2g, 20mmol), pentafluorophenol (2.2g, 24mmol), DMAP (0.5g, 4mmol) and 60mL dichloromethane into a three-necked flask, stir to dissolve EDCI (4.6g, 24mmol) was added to the system, and stirring continued for 36h, the system changed from turbidity to clear. After detecting the completion of the reaction by thin-layer chromatography, it was washed successively with distilled water (30×6 mL) and saturated brine (30×3 mL), dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain a light yellow solid. Recrystallization was performed with a mixed solvent of ethyl acetate and petroleum ether to obtain 4.3 g of white crystals (yield: 64%).

[0064] M.p.48.5-49.4℃. 1 H NMR(500MHz, CDCl 3 , ppm): δ3.18 (m, 1H, OCOCH), 2.83-2.81 (m, 4H, CHCCH 2 ), 2.14(t,2H,CHCCH 2 ); 13 C NMR(CDCl 3 ):δ(ppm)168.51(CHCOO), 142.04-13...

Embodiment 3

[0065] Example 3: Preparation of polynorbornene-poly(1,6-heptadiyne) block copolymers with different block ratios

[0066] In a 25mL Schlenk reaction tube, add N-3,5-difluorophenylnorbornenepyrrolidine (185.2mg, 0.75mmol), vacuum and replace with high-purity nitrogen 3 times, add 2.7mL tetrahydrofuran to make it completely dissolved. Add pentafluorophenyl 4-formate-1,6-heptadiyne (45.2mg, 0.15mmol) to another 25mL Schlenk reaction tube, vacuum and replace with high-purity nitrogen 3 times, add 0.3mL tetrahydrofuran to make it completely dissolved. Under a nitrogen atmosphere, weigh the Grubbs third-generation catalyst (8.8mg, 0.01mmol) in the third Schlenk tube, evacuate and replace with nitrogen three times, and then add 1mL of tetrahydrofuran. The reaction system was frozen by liquid nitrogen, evacuated and filled with nitrogen. After repeating the cycle 3 times, it was thawed; after preheating at 30°C for 10 minutes, the catalyst solution was quickly added to the N-3,5-diflu...

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Abstract

The invention provides a fluorine-containing high-dielectricity polynorbornene-poly(1,6-heptadiyne) block copolymer and a preparation method thereof. The copolymer comprises a fluorine-containing norbornene derivative and a fluorine-containing 1,6-pimelic acetylene monomer, wherein the norbornene derivative and the 1,6-pimelic acetylene monomer form the polynorbornene-poly(1,6-heptadiyne) block copolymer through continuous ring-opening metathesis polymerization (ROMP) and translocation cyclization polymerization (MCP). The copolymer disclosed by the invention has excellent dielectric properties, unique nano structure, good heat stability and environment stability; the preparation method is simple and feasible; the processability and the dielectric property of the material can be further improved through flexible transformation of a polymer side chain substituent and regulation and control on the ratio of two blocks; and the fluorine-containing high-dielectricity polynorbornene-poly(1,6-heptadiyne) block copolymer has a wide application prospect in the fields such as a thin-film capacitor and the like.

Description

Technical field [0001] The invention belongs to the technical field of high-dielectric polymer preparation, in particular to a fluorine-containing high-dielectric polynorbornene-poly(1,6-heptadiyne) block copolymer. Background technique [0002] The classic high dielectric materials are mostly inorganic ceramics and inorganic / organic composite materials, but the dielectric loss is large, the cost is high, the molding process is complicated, and the flexibility is poor. The polymer material has the advantages of low dielectric loss, easy processing, large area film formation, etc. The electroosmotic composite material obtained by doping conductive particles into the insulating polymer matrix has a significantly increased dielectric constant. However, there are still some obvious drawbacks in the application process, such as higher dielectric loss and strong frequency dependence. [0003] The copolymer involved in the present invention is a high-dielectric polymer material, and ther...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F232/08C08F238/00C08F2/38C08G61/08
Inventor 谢美然刘雯梅王俊芳刘春泽伍建华陈杰
Owner EAST CHINA NORMAL UNIV
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