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Method for preparing 1,4-stereoregular polytriazoles catalyzed by a ruthenium complex

A technology of stereoregular, ruthenium complexes, applied in the fields of polymer chemistry and materials science, can solve problems such as inability to provide, and achieve the effects of mild conditions, high polymerization efficiency and simple process

Active Publication Date: 2021-06-08
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method can only produce 1,5-stereoregular polytriazoles, but cannot provide 1,4-stereoregular polytriazoles, and small changes in the structure are likely to have an important impact on the properties of the polymer

Method used

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  • Method for preparing 1,4-stereoregular polytriazoles catalyzed by a ruthenium complex
  • Method for preparing 1,4-stereoregular polytriazoles catalyzed by a ruthenium complex
  • Method for preparing 1,4-stereoregular polytriazoles catalyzed by a ruthenium complex

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Experimental program
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Effect test

Embodiment 1

[0041] Ruthenium complex catalyzed M1 and M2 to prepare polytriazole P1:

[0042]

[0043] Wherein, the monomer M1 is 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); the monomer M2 is synthesized according to the published It was synthesized by the synthesis method in the literature (Hyperbranched polytriazoles: Clickpolymerization, regioisomeric structure, light emission, and fluorescent patterning. Macromolecules 2008, 41, 3808-3822).

[0044] Add 152mg (0.5mmol) of monomer M1, 180mg (0.5mmol) of monomer M2 and 9.2mg (0.01mmol) of tris(triphenylphosphine)carbonyl dihydroruthenium(II) into a 10mL polymerization tube, vacuumize and change nitrogen Three times, use a syringe to inject 1 mL of ultra-dry N,N-dimethylformamide. After the monomer is completely dissolved, put it into an oil bath at a constant temperature of 80°C and react for 5 hou...

Embodiment 2

[0049] Ruthenium complex catalyzed M1 and M3 to prepare polytriazole P2:

[0050]

[0051] Among them, the monomers M1 and M3 were 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).

[0052] Add 152mg (0.5mmol) of monomer M1, 239mg (0.5mmol) of monomer M3 and 9.2mg (0.01mmol) of tris(triphenylphosphine)carbonyl dihydrogenruthenium(II) into a 10mL polymerization tube, vacuumize and change nitrogen Three times, use a syringe to inject 1 mL of ultra-dry N,N-dimethylformamide. After the monomer is completely dissolved, put it into an oil bath at a constant temperature of 80°C and react for 5 hours. After the reaction is over, add 4 mL of chloroform to the polymerization tube for dilution, filter the obtained polymer solution through cotton and drop it into 110 mL of vigorously stirred (750 rpm) n-hexane / chloroform mixture (volume ratio 10:1) ...

Embodiment 3

[0056] Ruthenium complex catalyzed M1 and M4 to prepare polytriazole P3:

[0057]

[0058] Wherein, the monomer M1 is 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); the monomer M4 is synthesized according to the published It was synthesized according to the synthesis method in the literature (Metal-free click polymerization: Synthesis and photonic properties of poly(aroyltriazole)s. Adv. Funct. Mater. 2009, 19, 1891-1900).

[0059] Add 152mg (0.5mmol) of monomer M1, 307mg (0.5mmol) of monomer M4 and 9.2mg (0.01mmol) of tris(triphenylphosphine)carbonyl dihydrogenruthenium(II) into a 10mL polymerization tube, vacuumize and change nitrogen Three times, use a syringe to inject 1 mL of ultra-dry N,N-dimethylformamide. After the monomer is completely dissolved, put it into an oil bath at a constant temperature of 80°C and react for 5 hours. After...

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Abstract

The invention belongs to the technical field of polymer chemistry and discloses a method for preparing 1,4-stereoregular polytriazole by catalyzing a ruthenium complex. The method comprises the following steps: under the protection of an inert gas, performing click polymerization on a binary alkynyl compound and a binary azido compound in an organic solvent through the catalysis of a ruthenium complex, and subsequent processing to obtain a 1,4-stereoregular polymer triazole. The structural formula of 1,4-stereoregular polytriazole is formula (I). The method of the invention has simple conditions, high reaction efficiency, good atom economy and very high regioselectivity. The polytriazole prepared by the method of the invention is 1,4-stereoregular polytriazole, has high yield, high regularity, excellent processability and very good thermal stability.

Description

technical field [0001] The invention relates to the fields of macromolecule chemistry and materials science, in particular to a method for preparing 1,4-stereoregular polytriazole by azide-alkyne click polymerization catalyzed by a ruthenium complex. Background technique [0002] In the field of polymer science, the development of new efficient and selective polymerization reactions is crucial to prepare functional polymers with defined structures and unique properties. Click polymerization has attracted extensive attention from polymer scientists due to its advantages of high reaction efficiency, mild conditions, high atom economy, good functional group tolerance and high selectivity. However, the current research mainly focuses on copper-catalyzed azide-alkyne click polymerization, and there is little research on other metal-catalyzed azide-alkyne click polymerization, and in some cases, copper-catalyzed azide-alkyne click polymerization is not applicable. For example, be...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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