Method for preparing 1,5-stereoregular polytriazole by catalysis of nickel complex

A technology of stereoregular and nickel complexes, applied in the fields of polymer chemistry and materials science, to achieve the effects of high polymerization efficiency, high regioregularity and simple process

Active Publication Date: 2019-05-03
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these two methods have certain limitations. The former needs to be heated at 60°C, and the latter is only suitable for aromatic alkyne monomers and aromatic azide monomers.

Method used

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  • Method for preparing 1,5-stereoregular polytriazole by catalysis of nickel complex
  • Method for preparing 1,5-stereoregular polytriazole by catalysis of nickel complex
  • Method for preparing 1,5-stereoregular polytriazole by catalysis of nickel complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Nickel complex catalyzed M1 and M2 to prepare polytriazole P1:

[0045]

[0046] Wherein, the monomer M1 is synthesized according to the synthesis method in the published literature (Catalyst-free thiol-yne clickpolymerization: A powerful and facile tool for preparation of functional poly(vinylene sulfide)s. Macromolecules 2014,47,1325-1333); Monomer M2 was synthesized according to the synthesis method in the published literature (Hyperbranched polytriazoles: Click polymerization, regioisomeric structure, light emission, and fluorescent patterning. Macromolecules 2008, 41, 3808-3822).

[0047]Add 91.2 mg (0.2 mmol) of monomer M1, 72 mg (0.2 mmol) of monomer M2, 7.6 mg (0.04 mmol) of nickelocene, 23.1 mg (0.04 mmol) of 4,5-bisdiphenyl into a 10 mL polymerization tube Phosphine-9,9-dimethylxanthene and 65.2mg (0.2mmol) cesium carbonate, evacuate and change nitrogen for 3 times, inject 0.5mL ultra-dry N,N-dimethylformamide with a syringe, and react at room temperature ...

Embodiment 2

[0057] Nickel complex catalyzed M1 and M3 to prepare polytriazole P2:

[0058]

[0059] Wherein, the monomer M1 is synthesized according to the synthesis method in the published literature (Catalyst-free thiol-yne clickpolymerization: A powerful and facile tool for preparation of functional poly(vinylene sulfide)s. Macromolecules 2014,47,1325-1333); Monomer M3 was synthesized according to the synthesis method in the published literature (A recyclable and reusable supported Cu(I)catalyzed azide-alkyne click polymerization.Sci.Rep.2014,4,5107).

[0060] Add 91.2mg (0.2mmol) of monomer M1, 95.6mg (0.2mmol) of monomer M3, 7.6mg (0.04mmol) of nickelocene, 23.1mg (0.04mmol) of 4,5-diphenyl into a 10mL polymerization tube Phosphine-9,9-dimethylxanthene and 65.2mg (0.2mmol) cesium carbonate, evacuate and change nitrogen for 3 times, inject 0.5mL ultra-dry N,N-dimethylformamide with a syringe, at room temperature React for 30 minutes. After the reaction is over, add 4 mL of dichlo...

Embodiment 3

[0064] Nickel complex catalyzed M1 and M4 to prepare polytriazole P3:

[0065]

[0066] Wherein, the monomer M1 is synthesized according to the synthesis method in the published literature (Catalyst-free thiol-yne clickpolymerization: A powerful and facile tool for preparation of functional poly(vinylene sulfide)s. Macromolecules 2014,47,1325-1333); Monomer M4 was synthesized according to the synthesis method in the published literature (A recyclable and reusable supported Cu(I)catalyzed azide-alkyne click polymerization.Sci.Rep.2014,4,5107).

[0067] Add 91.2mg (0.2mmol) of monomer M1, 122.8mg (0.2mmol) of monomer M4, 7.6mg (0.04mmol) of nickelocene, 23.1mg (0.04mmol) of 4,5-diphenylene into a 10mL polymerization tube Phosphine-9,9-dimethylxanthene and 65.2mg (0.2mmol) cesium carbonate, evacuate and change nitrogen for 3 times, inject 0.5mL ultra-dry N,N-dimethylformamide with a syringe, at room temperature React for 30 minutes. After the reaction is over, add 4 mL of di...

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Abstract

The invention belongs to the technical field of high polymer chemistry, and discloses a method for preparing 1,5-stereoregular polytriazole by catalysis of nickel complex. The method includes: in thepresence of an organophosphine ligand and under alkaline condition, performing click polymerization on a binary alkynyl compound and a binary azide compound in an organic solvent under catalytic effect of the nickel complex, and performing post-treatment to produce the 1,5-stereoregular polytriazole as structure formula (I). The method is gentle in conditions and is high-effective in reaction, hasgreat atom economy, and has very high zone selectivity. The polytriazole in the invention is 1,5-stereoregular polytriazole, which has high zone regularity and high yield, and is excellent in processability and great in thermo-stability.

Description

technical field [0001] The invention relates to the fields of macromolecule chemistry and materials science, in particular to a method for preparing 1,5-stereoregular polytriazole by azide-alkyne click polymerization catalyzed by a nickel complex. Background technique [0002] In the field of polymer science, the development of efficient and selective polymerization reactions is crucial to prepare functional polymers with defined structures and unique properties. Click polymerization has attracted extensive attention due to its advantages of high reaction efficiency, mild conditions, atom economy, and good regioselectivity, and has been widely used in the fields of biomaterials, optoelectronic materials, and self-healing materials. However, the current research hotspots mainly focus on copper(I)-catalyzed azide-alkyne click polymerization, and there are very few studies on other metal-catalyzed azide-alkyne click polymerization. In addition, considering that copper(I)-catal...

Claims

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Application Information

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IPC IPC(8): C08G73/08
Inventor 唐本忠黄蝶秦安军胡蓉蓉赵祖金
Owner SOUTH CHINA UNIV OF TECH
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