Method for preparing 1,4-stereoregular polytriazole by copper ion liquid catalysis, 1,4-stereoregular polytriazole and application thereof

A stereoregular, liquid catalysis technology, applied in the production of bulk chemicals, chemical process analysis/design, instruments, etc., can solve few problems and achieve the effect of simple preparation method, mild conditions, and easy availability of reaction raw materials

Active Publication Date: 2019-01-25
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To the best of our knowledge, copper ionic liquid (Cu-IL)-catalyzed azide-alkyne cycloaddition reactions have been poorly studied

Method used

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  • Method for preparing 1,4-stereoregular polytriazole by copper ion liquid catalysis, 1,4-stereoregular polytriazole and application thereof
  • Method for preparing 1,4-stereoregular polytriazole by copper ion liquid catalysis, 1,4-stereoregular polytriazole and application thereof
  • Method for preparing 1,4-stereoregular polytriazole by copper ion liquid catalysis, 1,4-stereoregular polytriazole and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Copper ionic liquid catalyzed M1 and M2 to prepare polytriazole P1.

[0060]

[0061]Among them, the monomer M1 is synthesized according to the synthesis method in the published literature (Eur.J.Org.Chem., 2015, 2015, 4593); M2 is synthesized according to the published literature (Polym.Chem., 2014, 5, 2301) Synthetic method Synthetic. Wherein, the synthetic route of copper ionic liquid (Cu-IL) is as follows:

[0062]

[0063] Copper ionic liquid Cu-IL was synthesized according to the synthesis method in the published literature (Dalton Trans., 2011, 43, 11396). FT-IR (KBr disk), ν (cm -1 ): 3427, 2939, 2886, 1637, 1456, 1258, 1169, 1060, 1033, 641, 576, 520. The decomposition temperature is 188°C.

[0064] Add 25.0mg (0.1mmol) of monomer M1, 38.2mg (0.01mmol) of monomer M2 and 5mg (0.005mmol) of Cu-IL into a 10mL polymerization tube, vacuumize and change nitrogen for 3 times, and inject 2.5mL of ultra-dry N,N-dimethylformamide (DMF), after the monomer is co...

Embodiment 2

[0072] Copper ionic liquid catalyzed M3 and M4 to prepare anionic conjugated polytriazole P2. Among them, monomer M3 was purchased from TCI Company. M4 was synthesized according to the synthesis method in the published literature (Beilstein J.Org.Chem.2014, 10, 1166; Polym.Chem.2014, 5, 2301).

[0073]

[0074] Add 46.6mg (0.1mmol) of monomer M3, 43.0mg (0.1mmol) of monomer M4 and 9.9mg (0.01mmol) of Cu-IL into a 10mL polymerization tube, vacuum and change nitrogen for 3 times, and inject 2mL of ultra-dry DMF, after the monomer is completely dissolved, put it into an oil bath at a constant temperature of 50°C, and react for 2 hours. After the reaction was completed, 2 mL THF was added, and the obtained polymer solution was added dropwise into 60 mL of vigorously stirred methanol, left to stand, filtered, and dried to obtain polytriazole P2. Through measurement and analysis, the productive rate of final product polytriazole P2 is 89%, and weight-average molecular weight is...

Embodiment 3

[0077] Application of Anionic Conjugated Polytriazole P2 in Explosive Detection.

[0078] The detection of explosives is of great significance to national security and anti-terrorism. We used commercially obtained picric acid (PA) as an explosive model to verify the sensitive detection of anionic conjugated polytriazole P2 for explosives. Figure 5A It is the fluorescence spectrum of polytriazole P2 aqueous solution with different content of PA, [P2]=10μM, excitation wavelength: 352nm. 5B is the I of polytriazole P2 0 Stern-Volmer curve of / I-1 and PA concentration, where I is the fluorescence intensity of PA added, I 0 The fluorescence intensity without PA is shown, and the inset is the structural formula of PA. From Figure 5A It can be seen that with the increase of PA content, the fluorescence emission of polytriazole P2 gradually weakens until it is completely quenched, while the shape and position of the fluorescence curve do not change. From Figure 5B The Stern-Vo...

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Abstract

The invention discloses a method for preparing 1,4-stereoregular polytriazole by copper ion liquid catalysis. The method comprises the following steps: (1) under protection of inert gas, performing click polymerization on a binary alkynyl compound and a binary azide based compound in an organic solvent in the presence of copper ion liquid; (2) after reaction is ended, dissolving a product into theorganic solvent, adding the mixture into methyl alcohol to precipitate, collecting precipitates, and drying to constant weight, thereby obtaining 1,4-stereoregular polytriazole. The invention furtherdiscloses 1,4-stereoregular polytriazole and application thereof. The preparation method is efficient, gentle in condition, simple and liable to perform, and good in atomic economical efficiency; andthe prepared 1,4-stereoregular polytriazole is very high in molecular weight and yield. Obtained anionic conjugated polytriazole has potential application in aspects of biological detection and fluorescence detection; and the obtained tetraphenyl ethylene-diarylethene conjugated polytriazole can be used for anti-fake and duplicate materials.

Description

technical field [0001] The invention relates to 1,4-stereoregular polytriazoles, in particular to a method for preparing 1,4-stereoregular polytriazoles by azide-alkyne click polymerization catalyzed by copper ionic liquids and 1,4-stereoregular polytriazoles The application of azoles. Background technique [0002] The development and establishment of new polymerization methods and the preparation of polymers with unique structures and advanced functions are of great importance to materials science. Azide-alkyne click polymerization has become an important means to prepare 1,4-stereoregular polytriazoles with novel functions and topologies. In the past ten years, the catalytic systems of azide-alkyne click polymerization have emerged in an endless stream, and click polymerization has been widely developed. However, these catalytic systems still have some inevitable shortcomings, and the catalytic efficiency needs to be further improved. [0003] Ionic liquids (ILs) and ion...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/08G01N21/25G01N21/64G01N21/84G09F3/02G16C20/10
CPCC08G73/08G01N21/25G01N21/643G01N21/84G01N2021/6432G09F3/02G09F3/0294Y02P20/54
Inventor 唐本忠李白雪秦安军赵祖金胡蓉蓉王志明
Owner SOUTH CHINA UNIV OF TECH
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