Polyphenyltriazole formate, and preparation method and application thereof

A technology of polyphenyltriazole formate and phenylpropiolic acid dibasic ester, which is applied in the field of polymer chemistry and material science, can solve the problem of cytotoxicity affecting the photoelectric performance of polymers, polytriazole with poor solubility and difficult to remove. and other issues, to achieve the effects of wide substrate applicability, good functional group compatibility, and prevention of explosive attacks

Active Publication Date: 2016-12-21
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Because the triazole ring can coordinate with the metal, the solubility of the polytriazole obtained by this type of polymerization is often poor; at the same time, the residual metal catalyst in the polymer is usually difficult to remove, because the metal catalyst, especially copper, will Produce cytotoxicity and affect the optoelectronic properties of polymers, thus limiting the application of this type of polymerization in the fields of optoelectronics and biomedicine
In recent years, Qin and Tang et al. have developed a class of metal-free click polymerization of active alkynes and organic azides; however, the alkyne monomers used in this type of polymerization are limited to terminal alkyne compounds.
In 2012, their research group reported a metal-free catalyzed polymerization reaction of active internal alkynes (phenyne ketones) and organic azide compounds, but the synthesis of phenyne ketone monomers requires the use of highly active reagents such as acid chlorides and noble metal catalysts, which limit the application of this type of polymerization
However, the preparation of polyphenyltriazole formate with AIE properties by the polymerization of phenylpropiolate and organic azides without metal catalysis has not been reported.

Method used

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  • Polyphenyltriazole formate, and preparation method and application thereof
  • Polyphenyltriazole formate, and preparation method and application thereof
  • Polyphenyltriazole formate, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039]

[0040]Add 1.14 g (5 mmol) of bisphenol A, 3.10 g (15 mmol) of DCC, 0.244 g (2 mmol) of DMAP, and 0.38 g (2 mmol) of TsOH into a 250 mL two-necked flask, vacuumize and fill with nitrogen three times. Add 100 mL of dichloromethane and stir to dissolve, then dissolve 1.61 g (11 mmol) phenylpropylic acid in 20 mL of dichloromethane under an ice-water bath environment, and add it dropwise to the reaction system through a constant pressure dropping funnel. The reaction was stirred overnight at room temperature, filtered, washed with dichloromethane, and the filtrate was spin-dried to obtain a crude product, which was separated and purified by column chromatography, dried in vacuo to constant weight, and 1.89 g of a white solid (yield 78.1% ), which is the first monomer phenylpropiolic acid dibasic ester monomer. 1 H NMR (400 MHz, DMSO- d 6 ), δ (TMS,ppm): 7.71 (d, J = 7.4 Hz, 4H), 7.62 (t, J = 7.4 Hz, 2H), 7.52 (t, J = 7.5Hz, 4H), 7.33 (d, J = 8.6 Hz, 4H), 7...

Embodiment 2

[0048] The phenylpropiolic acid dibasic ester monomer and the binary organic azide monomer are the same as in Example 1. Add 48.4 mg (0.1 mmol) of the first monomer and 44.2 mg (0.1 mmol) of the second monomer into a 10 mL polymerization tube, vacuumize the system and fill with nitrogen, repeat three times, then add 0.2 mL of dry DMF, and wait for a single After the body is completely dissolved, react at 150°C for 1 hour, cool to room temperature and dilute with 5 mL of chloroform, and drop the solution into 200 mL of vigorously stirred n-hexane through a dropper plugged with cotton, let stand, filter, Dry to constant weight to obtain a polymer with a yield of 85.1%. GPC results show: M w = 10100, PDI = 1.4. The polymer also has good solubility and thermal stability; due to the tetraphenylethylene group containing aggregation-induced luminescence activity, the polymer also has aggregation-induced luminescence properties and can be used for the detection of explosives, as ...

Embodiment 3

[0050] The phenylpropiolic acid dibasic ester monomer and the binary organic azide monomer are the same as in Example 1. Add 48.4 mg (0.1 mmol) of the first monomer and 44.2 mg (0.1 mmol) of the second monomer into a 10 mL polymerization tube, vacuumize the system and fill with nitrogen, repeat three times, then add 0.2 mL of dry DMF, and wait for a single After the body is completely dissolved, react at 150°C for 4 hours, cool to room temperature and dilute with 5 mL of chloroform, and add the solution dropwise into 200 mL of vigorously stirred n-hexane through a dropper plugged with cotton, let stand, and filter , and dried to constant weight to obtain a polymer with a yield of 78.3%. GPC results show: M w = 24800, PDI = 1.8. The polymer also has good solubility and thermal stability; due to the tetraphenylethylene group containing aggregation-induced luminescence activity, the polymer also has aggregation-induced luminescence properties and can be used for the detectio...

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Abstract

The invention discloses a polyphenyltriazole formate, and a preparation method and application thereof. A phenylpropargylic acid dibasic ester monomer and a dibasic organic azido monomer used as raw materials are subjected to polymerization reaction in a polar aprotic solvent to obtain the polyphenyltriazole formate. The preparation method has the advantages of accessible reaction raw materials and no byproduct generation in the polymerization reaction process, and conforms to the atom economy. The polymerization reaction has wide substrate applicability and favorable functional group compatibility, and is convenient for introducing multiple functional groups. The polymerization reaction does not use any metal catalyst, and thus, can eliminate the influence of catalyst residues on the biological and photoelectric properties of the polymer material. The polyphenyltriazole formate has the advantages of favorable processability, higher heat stability, higher degradability and higher aggregation-induced luminescence, and has potential application values in the aspects of optical plastics, biomedical materials, fluorescence detection and the like.

Description

technical field [0001] The invention belongs to the fields of macromolecule chemistry and material science, and in particular relates to a polyphenyltriazole formate and a preparation method and application thereof. Background technique [0002] The development of new monomers and polymerization reactions are very important for the synthesis of polymers and the preparation of polymer functional materials. At present, most of the polymerization reactions are developed from the reactions of small organic molecules. The 1,3-dipolar cycloaddition reaction of alkynes and organic azides to 1,2,3-triazoles under heating was reported as early as 1893. However, this reaction has not been widely used due to the lack of regioselectivity and slow reaction rate. In 2002, the Meldal of Denmark and the Sharpless research group of the United States independently discovered that monovalent copper can catalyze the reaction of terminal alkynes and organic azide compounds, and only generate 1,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/08C08L79/06G01N21/64C07D249/06
CPCC07D249/06C08G73/08C08L79/06G01N21/6428
Inventor 李红坤袁伟李永舫
Owner SUZHOU UNIV
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