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

A technology of polynorbornene and block copolymers, which is applied in the field of high dielectric polymer preparation, and can solve problems related to dielectric materials that have not been reported yet

Inactive Publication Date: 2015-09-16
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Polyacetylene is the simplest conductive polymer, but the preparation of d...

Method used

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

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

Embodiment 2

[0062] Example 2: Synthesis of 4-pentafluorophenyl formate-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 the three-necked flask, stir and dissolve , EDCI (4.6g, 24mmol) was added to the system, stirring was continued for 36h, and the system changed from cloudy to clear. After the completion of the reaction was detected by thin-layer chromatography, it was washed with distilled water (30×6 mL) and saturated brine (30×3 mL) successively, dried over anhydrous sodium sulfate, and the solvent was removed by rotary evaporation to obtain a light yellow solid. Recrystallization was carried out 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 (CHC...

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-difluorophenylnorbornene pyrrolidine (185.2mg, 0.75mmol), vacuumize and replace with high-purity nitrogen three times, add 2.7mL tetrahydrofuran, make it completely dissolved. In another 25mL Schlenk reaction tube, add 4-pentafluorophenyl formate-1,6-heptadiyne (45.2mg, 0.15mmol), vacuumize and replace with high-purity nitrogen three times, add 0.3mL tetrahydrofuran, make it completely dissolved. Under a nitrogen atmosphere, weigh Grubbs third-generation catalyst (8.8 mg, 0.01 mmol) into a third Schlenk tube, vacuumize and replace with nitrogen three times, and then add 1 mL of tetrahydrofuran. The reaction system was frozen with liquid nitrogen, vacuumed and filled with nitrogen, and then thawed after repeating the cycle 3 times; after preheating at 30°C for 10 minutes, the catalyst solution was quickly added t...

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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. Polymer materials have the advantages of low dielectric loss, easy processing, and large-area film formation. The electroosmotic composite material obtained by doping conductive particles into an insulating polymer matrix has a significantly increased dielectric constant. However, there are still some obvious disadvantages in the application process, such as high dielectric loss and strong frequency dependence. [0003] The copolymer involved in the present invention is a high dielectric polymer material, and...

Claims

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Application Information

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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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