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Norbornene monomer, as well as polymer and preparation method thereof

A norbornene and polymer technology, which is applied in the fields of norbornene and its polymers and preparation, can solve the problem of large distance between donor side chain units and acceptor side chain units, weakened π-π interaction, side chain Problems such as the reduction of arrangement regularity

Inactive Publication Date: 2013-09-11
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the alternating copolymers in this report can only be realized by the ring-opening metathesis polymerization of donor-type norbornene-type monomers and acceptor-type cyclooctene-type monomers. The distance between the unit and the acceptor side chain unit is too large, which in turn reduces the arrangement regularity of the side chain and weakens the π-π interaction

Method used

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  • Norbornene monomer, as well as polymer and preparation method thereof
  • Norbornene monomer, as well as polymer and preparation method thereof
  • Norbornene monomer, as well as polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Example 1: Preparation of N-(4-tert-butyldimethylsilyloxyphenyl) norbornene pyrrolidine (M1)

[0056] The synthetic route is as follows:

[0057]

[0058] Specific steps:

[0059] (1) Dissolve 150 ml of norbornene dioic anhydride (8.2 g, 50 mmol) and 4-aminophenol (5.46 g, 50 mmol) in glacial acetic acid, and react at room temperature for 15 h. The reaction solution was dropped into 500 ml of ice water, and a large amount of white precipitates were precipitated immediately. After filtration, vacuum drying was performed for 48 h to obtain 11 g of white powder, yield: 86%.

[0060] (2) Under a nitrogen atmosphere, the product N-(4-hydroxyphenyl) norbornene imide (6.4 g, 25 mmol) obtained in step (1) was dissolved in 120 ml of dry CH 2 Cl 2 , TBS-Cl (7.5 g, 50 mmol) and imidazole (3.4 g, 50 mmol) were added under ice cooling. A large amount of salt was formed immediately, and it was naturally raised to room temperature, and reacted for 12 h. Remove the imidazolium ...

Embodiment 2

[0062] Example 2: Preparation of N-(3,5-difluorophenyl) norbornene imide (M2)

[0063] The synthetic route is as follows:

[0064]

[0065] Specific steps: under nitrogen atmosphere, dissolve norbornene dianhydride (9.84 g, 60 mmol) and 3,5-difluoroaniline (6.45 g, 50 mmol) in 50 mL of anhydrous 1,2-dichloroethane , 0.3 equivalents of DMAP (1.83 g, 15 mmol) was added to the reaction solution. Reflux at 90 °C for 36 h, the reaction was complete. After repeated washing, extraction and recrystallization, 11.2 g of white crystals were obtained with a yield of 81.5%. The resulting product is N-(3,5-difluorophenyl)norbornenimide (M2). 1 H NMR (500 MHz, CDCl 3 , δ): 6.83 (m, 1H, CFC H CF), 6.81-6.77 (m, 2H, NCC H C H ), 6.25 (s, 2H, C H =C H ), 3.51 (s, 2H, CHC H CO), 3.43 (s, 2H, C H CH 2 C H ), 1.80-1.60 (m, 2H, CHC H 2 CH); 13 C NMR (500 MHz, CDCl 3 , δ): 175.93 (CH C =O), 163.66 (CH C F), 161.79 (N C CH), 134.66 (CH= C HCH), 110.04 (NC C H), 104.1 (FC C ...

Embodiment 3

[0066] Example 3: Preparation of electron donor type norbornene homopolymer

[0067] In a 25 mL Schlenk reaction tube, add electron-donor norbornene-based monomer N-(4-tert-butyldimethylsilyloxyphenyl)norbornene pyrrolidine (formula (M1), 341 mg, 1 mmol) with 3 mL CH 2 Cl 2 , Grubbs third generation catalyst (H 2 IMes)(3-BrPy) 2 (Cl) 2 Ru(CHPh) (16.5 mg, 0.02 mmol) with 2 mL CH 2 Cl 2 , the molar ratio of monomer to catalyst is 50:1. The two reaction tubes were frozen with liquid nitrogen, evacuated, and replaced with nitrogen three times. After thawing and rising to room temperature, the monomer reaction tube was placed in an oil bath at 30 °C for 5 min. Under a nitrogen atmosphere, the catalyst solution was added into the monomer reaction tube with a syringe, and the system was placed in an oil bath at 30 °C for 1 h. Stop the reaction, add 2 drops of vinyl ether to the system, and stir at room temperature for 30 min. The reaction solution was dropped into methanol ...

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Abstract

The invention relates to an electronic donor / receptor type norbornene monomer, as well as a polymer and a preparation method thereof. Being prepared from the electronic donor / receptor type norbornene monomer by means of ring-opening metathesis polymerization in the presence of a Grubbs ruthenium catalyst, the norbornene polymer disclosed by the invention has good stereoregularity and high Pi-Pi interaction between molecular chains, and contributes to charge transfer. The preparation method provided by the invention is simple and easy to implement and can realize regulation and control of performances by flexible transformation by a side chain substituent group, so the preparation method has wide application prospect in fields of photo-elements, electric elements, biomacromolecule, etc.

Description

technical field [0001] The invention relates to norbornene and its polymers and a preparation method, in particular to a preparation method of an electron donor / acceptor type norbornene monomer and its homopolymer and random copolymer. Background technique [0002] The research on ring-opening metathesis polymerization began in the middle of the 1950s. It is an important means of synthesizing new functionalized polymers. It has been a research hotspot in the field of polymer chemistry for nearly 20 years. A typical representative of the single-component alkylene / metal carbene metathesis catalyst developed in the early 1980s is the Schrock molybdenum catalyst [Mo(NAr)(=CHCMe 2 Ph)(OR) 2 ] and Grubbs ruthenium catalyst [RuCl 2 (PCy 3 ) 2 (CHPh), RuCl 2 (PCy 3 )(SIMes)(CHPh), (H 2 IMes)(3-BrPy) 2 (Cl) 2 Ru(CHPh)], they have good thermal stability, high catalytic activity, good tolerance to functional groups such as alcohols, carboxylic acids, esters, air and moisture, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/76C07F7/18C08G61/12
Inventor 谢美然曾驰廖杨尤泽旺高丹怡
Owner EAST CHINA NORMAL UNIV
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