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Hyperbranched polytriazole formate as well as preparation method and application thereof

A technology of polytriazole formate and polymerization reaction, applied in the fields of polymer chemistry and material science, can solve the problems of affecting the biological and optoelectronic properties of polymers, difficult to remove copper catalysts, poor polymer solubility, etc. Effects of functional group compatibility, elimination of cytotoxicity, good processability

Active Publication Date: 2012-07-18
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In 2008, Katritzky's research group used A 2 +B 3 Type monomers prepare hyperbranched polymers under the catalysis or thermal polymerization conditions of copper sulfate and sodium ascorbate, the solubility of the obtained polymers is relatively poor, and the reaction time is longer (J.Polym.Sci., PartA: Polym.Chem .2008, 46, 238)
Our research group recently adopted A 2 +B 3 A polymer with AIE performance has been prepared under monovalent copper catalysis (Chinese patent, application number: 201010590712.5, J.Mater.Chem.2011, 21, 4056, ), but the residual copper catalyst in the polymer is difficult to remove clean, tends to affect the biological and optoelectronic properties of the polymer

Method used

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  • Hyperbranched polytriazole formate as well as preparation method and application thereof
  • Hyperbranched polytriazole formate as well as preparation method and application thereof
  • Hyperbranched polytriazole formate as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] (1) Synthesis of the first monomer containing a binary azide group

[0041] Add 9.81g (50mmol) of 4-methylbenzophenone and 6.54g (100mmol) of zinc powder into a 250mL two-necked flask, vacuum three times with nitrogen, add 100mL of tetrahydrofuran, and add 5.56mL of titanium tetrachloride dropwise under ice-cooling (50mmol), after the reaction system was returned to room temperature, heated to reflux for 12h, cooled, filtered, and spin-dried, the resulting crude product was separated and purified by a chromatographic column, and dried in vacuo to obtain 8.59g (95.3% yield) of a white solid, which was first intermediate. 1 H NMR (400MHz, CDCl 3 ), δ(TMS, ppm): 7.81(d, 2H), 7.74(d, 2H), 7.54(t, 1H), 7.08(m, 10H), 6.98(m, 8H), 2.23(d, 6H) .

[0042] Take 7.21g (20mmol) of the first intermediate, 7.48g (40mmol) of NBS, and 0.05g (0.2mmol) of BPO into a 250mL double-necked flask, vacuum three times with nitrogen, add 125mL of carbon tetrachloride to dissolve, heat and ref...

Embodiment 2

[0055] (1) The synthesis of the first monomer is the same as in Example 1.

[0056] (2) The second monomer The synthesis is the same as in Example 1.

[0057] (3) Preparation of hyperbranched polytriazole formate

[0058] Add 66.3mg (0.15mmol) of the first monomer, 27.6mg (0.10mmol) of the second monomer and 1mL of N,N-dimethylformamide into a 10mL polymerization tube. After the monomer is completely dissolved, raise the temperature to 60°C React for 5 hours. After the reaction solution was diluted with 5 mL of chloroform, it was added dropwise into 200 mL of rapidly stirring n-hexane to obtain a white flocculent precipitate. Stand overnight, filter and dry to obtain 73.0 mg of polymer (yield 77.7%). GPC results show: M w = 5100, PDI = 2.63. Other characterization results are the same as in Example 1.

Embodiment 3

[0060] (1) The synthesis of the first monomer is the same as in Example 1.

[0061] (2) The second monomer The synthesis is the same as in Example 1

[0062] (3) Preparation of hyperbranched polytriazole formate

[0063] Add 66.3mg (0.15mmol) of the first monomer, 33.2mg (0.12mmol) of the second monomer and 0.5mL N,N-dimethylformamide into a 10mL polymerization tube, and after the monomer is completely dissolved, heat up to 60 °C for 12 hours. After the reaction solution was diluted with 5 mL of chloroform, it was added dropwise into 200 mL of rapidly stirring n-hexane to obtain a white flocculent precipitate. Stand overnight, filter and dry to obtain 82.4 mg of polymer (yield 84.7%). GPC results show: M w = 13000, PDI = 5.27. Other characterization results are the same as in Example 1.

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Abstract

The invention discloses hyperbranched polytriazole formate as well as a preparation method and application thereof. The preparation method of hyperbranched polytriazole formate comprises the following steps: firstly, synthesizing binary azide containing a tetraphenyl ethylene unit; then synthesizing a ternary ester compound containing alkynyl based on ternary alcohol and propiolic acid as raw materials; and finally, carrying out non-metal-catalytic 'click' polymerization reaction under the heating condition in a polar solvent by utilizing the azide and the alkynyl-containing ester compound soas to obtain a target polymer in high yield. The hyperbranched polytriazole formate prepared by using the method is high in 1,4-stereoregularity, good in workability and high in thermal stability, degradability, illumination patterning and aggregation-induced emission property. The invention also discloses application of hyperbranched polytriazole formate in detection of a polynitroarene explosive.

Description

technical field [0001] The invention relates to the fields of polymer chemistry and material science, in particular to a novel hyperbranched polytriazole formate and its preparation method and application. Background technique [0002] In the 1960s, German chemist Rolf Huisgen first studied the 1,3-dipolar cycloaddition reaction of cyclic triazoles prepared from organic azide and alkyne compounds (Chem. Ber. 1967, 100, 2494). However, due to the slow reaction rate and the lack of stereoselectivity of the product, this reaction has not been widely used. In 2002, the Meldal and Sharpless research groups independently reported the monovalent copper salt catalyzed azide-alkynyl cycloaddition reaction, and found that the reaction rate was greatly accelerated, and the product was stereoselective, only generating 1,4-disubstituted 1,2,3-triazole compounds (J.Org.Chem.2002, 67, 3057, Angew.Chem., Int.Ed.2011, 40, 2004). Immediately, Sharpless et al named the reaction "click chemis...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/06C09K11/06G01N21/64
Inventor 李红坤秦安军唐本忠孙景志
Owner ZHEJIANG UNIV
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