A kind of hyperbranched polyphenyltriazole formate and its preparation method and application

A technology of polyphenyltriazole formate and phenylpropiolic acid tribasic ester, which is applied in the fields of polymer chemistry and material science, can solve the problems of limited application range, quenching, and weakened luminescence, and achieve good compatibility, Good thermal stability, the effect of preventing explosive attacks

Active Publication Date: 2020-01-14
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this type of polymerization requires the use of metal catalysts, because the metal catalyst residue will affect the performance of the polymer, thus limiting the scope of application of this type of polymerization
[0004] In addition, traditional polymer luminescent materials often emit strongly in the dilute solution state, while the luminescence is weakened or completely quenched in the aggregated state, which limits the scope of use of such materials.

Method used

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  • A kind of hyperbranched polyphenyltriazole formate and its preparation method and application
  • A kind of hyperbranched polyphenyltriazole formate and its preparation method and application
  • A kind of hyperbranched polyphenyltriazole formate and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] (1) Synthesis of monomers

[0041] Add 0.4604 g (5 mmol) glycerol, 4.6402 g (22.5 mmol) DCC, 0.3678 g (3 mmol) DMAP, 0.5702 g (3 mmol) to a 250 ml two-necked flask p -TsOH, pumping N 2Three times, 100 ml of DCM was added to dissolve. In an ice-water bath environment, 2.5574 g (17.5 mmol) of phenylpropylic acid was dissolved in 20 ml of DCM and slowly added to the reaction system. The reaction was stirred overnight at room temperature. After the reaction was completed, suction filtration was performed, the filtrate was spin-dried, and the crude product was separated and purified by column chromatography. After drying to constant weight, 1.7 g of light yellow solid was obtained (71.4% yield), which was the first monomer phenylpropiolic acid tribasic ester monomer. 1 H NMR (400 MHz, CDCl 3 ) , δ 7.61 (d, J = 6.4 Hz, 6H), 7.46 (d, J = 7.0Hz, 3H), 7.38 (t, J = 7.0 Hz, 6H), 5.52 (s, 1H), 4.52 (dt, J = 11.8, 7.4 Hz, 4H).

[0042] (2) Preparation of polymer

[004...

Embodiment 2

[0047] The phenylpropiolic acid tribasic ester monomer and the dibasic azide monomer are the same as in Example 1. Add 47.7 mg (0.1 mmol) of the first monomer phenylpropiolate triglyceride and 54 mg (0.15 mmol) of the second monomer binary organic azide to a 10 mL polymeric tube with a sidearm. Evacuate the polymer tube and fill it with N through the side arm 2 Three times, add 0.25 mL of dry DMF and stir to dissolve. The system was placed at 100°C for 2 h. After the reaction, it was cooled to room temperature, diluted with 5 mL of chloroform, and added dropwise to 200 mL of vigorously stirred n-hexane through a dropper plugged with cotton. Stand still, filter, and dry to constant weight to obtain a polymer. Yield: 77.8%. GPC results show: M w = 4600, PDI = 1.42, has good processability and thermal stability.

Embodiment 3

[0049] The phenylpropiolic acid tribasic ester monomer and the dibasic azide monomer are the same as in Example 1. Add 47.7 mg (0.1 mmol) of the first monomer phenylpropiolate triglyceride and 54 mg (0.15 mmol) of the second monomer binary organic azide to a 10 mL polymeric tube with a sidearm. Pump N into the polymer tube through the side arm 2 Three times, add 0.25 mL of dry DMF and stir to dissolve. The system was placed at 100°C for 4 h. After the reaction, it was cooled to room temperature, diluted with 5 mL of chloroform, and added dropwise to 200 mL of vigorously stirred n-hexane through a dropper plugged with cotton. Stand still, filter, and dry to constant weight to obtain a polymer. Yield: 97.5%. GPC results show: M w = 19200, PDI = 2.46, has good processability and thermal stability.

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Abstract

The invention discloses a hyperbranched polyphenyltriazole formate, a preparation method and application thereof. Using phenylpropiolic acid tribasic ester and binary organic azide monomer, in polar aprotic solvent, heating and reacting for a period of time to obtain hyperbranched polyphenyltriazole formic acid ester. The reaction raw materials in the present invention are easy to obtain, and no by-products are generated during the polymerization process, which conforms to atom economy. The substrate of the polymerization reaction has a wide range of applications, has good compatibility with functional groups, and can easily introduce functional groups. At the same time, no metal catalyst is used in the preparation process of the polymer, which avoids the impact of catalyst residue on the biological activity and photoelectric performance of the polymer. Because the polymer contains a tetraphenylethylene structure, the polymer has good aggregation-induced luminescent properties, and can be used as a chemical sensor to detect polynitroaromatic explosives with high sensitivity.

Description

technical field [0001] The invention belongs to the fields of polymer chemistry and material science, and in particular relates to a hyperbranched polyphenyltriazole formate and a preparation method and application thereof. Background technique [0002] Hyperbranched polymers are a class of macromolecules with three-dimensional structure and high branching, which have the characteristics of low viscosity, difficult to crystallize, good solubility, a large number of terminal functional groups and high reactivity. Due to their unique structure and properties, hyperbranched polymers have been widely used in coatings, additives, drug and catalyst carriers, optoelectronic materials and other fields. With the unremitting efforts of polymer chemists, more and more functional hyperbranched polymers have been synthesized. However, the preparation of these polymers often requires strict experimental conditions and the use of metal catalysts, and it is difficult to completely remove t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/06C07C67/08C07C69/618
CPCC07C67/08C08G73/0644C07C69/618
Inventor 李红坤袁伟李永舫
Owner SUZHOU UNIV
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