Multi-component polymerization method based on alkyne and sulfonyl azide as well as sulfonyl-containing polymer and application

A binary sulfonyl azide and sulfonyl azide technology, applied in analytical materials, material excitation analysis, instruments, etc., can solve problems such as complex monomer design, lack, and limited development of functional materials, and achieve atom economy High, easy to separate, unique application value effect

Active Publication Date: 2019-01-08
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are few reports on the preparation of functional polymers containing sulfonyl groups with complex structures, such as sulfonyl polymers containing iminocoumarin, quinoline, amidine, thiocyanate or selenocyanate radicals, mainly Because the preparation of such functional polymers requires multi-step synthesis, complex monomer design and harsh conditions
The lack of a simple and efficient preparation method severely limits the development of such functional materials

Method used

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  • Multi-component polymerization method based on alkyne and sulfonyl azide as well as sulfonyl-containing polymer and application
  • Multi-component polymerization method based on alkyne and sulfonyl azide as well as sulfonyl-containing polymer and application
  • Multi-component polymerization method based on alkyne and sulfonyl azide as well as sulfonyl-containing polymer and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Polymer P1 was prepared by the multicomponent polymerization of the binary alkyne compound 1a, the binary sulfonyl azido compound 2a and the third component compound 3:

[0059]

[0060] Among them, monomer 1a is synthesized according to the synthesis method in the published literature (Macromolecules, 2014, 47, 1325), and monomer 2a is synthesized according to the synthesis method in the published literature (J. Energ. Mater., 2007, 25, 79) Synthesized by method, the monomer 3 can be purchased directly.

[0061] Take a 25mL Schlenk polymerization tube with a branch, and add magnetons, monomer 1a (0.10mmol, 33mg), monomer 2a (0.10mmol, 38mg), monomer 3 (0.25mmol, 30mg) and CuCl (0.02mmol, 2mg), vacuumize and change nitrogen for 3 times, add 2mL of anhydrous DCM to it with a syringe, and stir the solution evenly; add Et 3 N (0.30mmol, 42μL), stirred at 40°C for 1.5h, stopped the reaction, cooled to room temperature; added 1mL DMF to dilute the reaction solution, pass...

Embodiment 2

[0064] When monomer 1b is used to replace monomer 1a in Example 1, it is prepared by multi-component polymerization of binary alkyne compound monomer 1b, binary sulfonyl azide compound monomer 2a and third component compound monomer 3 Polymer P2:

[0065]

[0066] Wherein, monomer 1b is synthesized according to the synthesis method in the published literature (Polym.Chem.2012, 3, 1481). The process for preparing polymer P2 was similar to the process for preparing polymer P1 described above.

[0067] Polymer P2 has a yield of 96%, a weight average molecular weight of 37700 g / mol, and a PDI of 2.85. The detection results of the polymer for different metal ions are as follows: figure 2 shown. figure 2 It shows that different metal ions have different degrees of fluorescence quenching of polymer P2 solution. The polymer has the performance of selectively responding to ruthenium ions and can be used to detect ruthenium ions.

[0068] The different concentrations of P2 in ...

Embodiment 3

[0070] Polymer P3 was prepared from the multicomponent polymerization of the binary alkyne compound 1b, the binary sulfonyl azido compound 2a and the third component compound 4:

[0071]

[0072] Among them, the monomer 4 can be purchased directly.

[0073] Take a 25mL Schlenk polymerization tube with a branch, add magneton, monomer 1b (0.10mmol, 38mg), monomer 2a (0.10mmol, 38mg), monomer 4 (0.25mmol, 30mg) and CuCl (0.02mmol, 2mg), vacuumize and change nitrogen for 3 times, add 2mL DCM to it with a syringe, and stir the solution evenly; add Et 3 N (0.30mmol, 42μL), stirred at 40°C for 0.5h, stopped the reaction, cooled to room temperature; added 1mL DMF to dilute the reaction solution, passed the diluted reaction solution through a glass dropper filter device with cotton, and gradually Add dropwise to 150mL of high-speed stirring methanol to precipitate, after standing still, filter with filter paper, rinse the product on the filter paper with a large amount of methanol,...

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Abstract

The invention belongs to the technical field of a macromolecular polymer, and discloses a multi-component polymerization method based on alkyne and sulfonyl azide as well as a sulfonyl-containing polymer and application. The multi-component polymerization method comprises the step of performing multi-component polymerization reaction on a binary alkynyl compound, a binary sulfonyl azide compound and a third component compound under the protective atmosphere and through the effect of a univalent copper catalyst to obtain the sulfonyl-containing polymer, wherein the third component compound is acyanophenyl compound containing hydroxyl or amino, a formyl-containing thiophenol potassium compound, an amino-containing benzoyl compound, ammonium salt, ammonia, thiocyanate or selenium cyanate. The method is mild in polymerization conditions, simple in process, high in polymerization efficiency, large in product molecular weight and high in atom economy; furthermore, a functional element containing the complex structure can be constructed in situ simply and efficiently. The obtained sulfonyl-containing polymer is applied in the fields of fluorescence detection, metal ion detection, organicphotoelectric materials and antibacterial materials.

Description

technical field [0001] The invention belongs to the field of polymer preparation, and in particular relates to a multi-component polymerization method based on alkyne and sulfonyl azide, a sulfonyl group-containing polymer prepared therefrom and the application of the polymer. Background technique [0002] The development of new polymerization reactions and the preparation of polymers with unique structures and advanced functions are crucial to materials science. With the increasing demand for advanced materials, functionalized polymers with complex structures have received increasing attention. [0003] Introducing sulfonyl groups and some functional units into the polymer structure can endow the material with special photoelectric properties and biological activities. At present, there are few reports on the preparation of functional polymers containing sulfonyl groups with complex structures, such as sulfonyl polymers containing iminocoumarin, quinoline, amidine, thiocya...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/06C08G73/02G01N21/64G01N33/00
CPCC08G73/0253C08G73/0273C08G73/0688G01N21/64G01N33/00
Inventor 唐本忠胡蓉蓉徐立国黄玉章秦安军赵祖金
Owner SOUTH CHINA UNIV OF TECH
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