A kind of polyphenyltriazole formate and its preparation method and application

A technology of polyphenyltriazole formate and phenylpropiolic acid dibasic ester, which is applied in the fields of polymer chemistry and material science, can solve the problem of cytotoxicity affecting the photoelectric properties 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: 2018-06-19
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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

Examples

Experimental program
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Effect test

Embodiment 1

[0039]

[0040] Add 1.14 g (5 mmol) bisphenol A, 3.10 g (15 mmol) DCC, 0.244 g (2 mmol) DMAP, 0.38 g (2 mmol) TsOH to a 250 mL two-necked flask, and vacuum and fill with nitrogen three times. Add 100 mL of dichloromethane and stir to dissolve, then dissolve 1.61 g (11 mmol) of phenylpropynic acid in 20 mL of dichloromethane in an ice-water bath, 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 and dried to constant weight in vacuo to obtain 1.89 g of white solid (yield: 78.1%) ), is the first monomer phenylpropynoic 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 =7.5 Hz, 4H), 7.33 (d, J = 8.6 Hz, 4H), 7.21 (d, J = 8.6 Hz, 4H), 1.68 (s, 6H)...

Embodiment 2

[0048] The phenylpropynoic 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 to a 10 mL polymerization tube, vacuum and fill the system with nitrogen, repeat three times, and then add 0.2 mL of dry DMF. 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 add the solution dropwise to 200 mL of vigorously stirred n-hexane through a cotton-plugged dropper, let stand and filter After drying to constant weight, the polymer was obtained with a yield of 85.1%. GPC results show: M w = 10100, PDI =1.4. The polymer also has good solubility and thermal stability; because it contains tetraphenyl vinyl groups with aggregation-inducing luminescence activity, the polymer also has aggregation-inducing luminescence properties and can be used for the detection of explosives, as in Ex...

Embodiment 3

[0050] The phenylpropynoic 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 to a 10 mL polymerization tube, vacuum and fill the system with nitrogen, repeat three times, and then add 0.2 mL of dry DMF. After the body is completely dissolved, react at 150°C for 4 hours. After cooling to room temperature, dilute with 5 mL of chloroform, and add the solution dropwise to 200 mL of vigorously stirred n-hexane through a cotton-plugged dropper, let stand and filter After drying to constant weight, the polymer was obtained with a yield of 78.3%. GPC results show: M w = 24800, PDI =1.8. The polymer also has good solubility and thermal stability; because it contains tetraphenyl vinyl groups with aggregation-inducing luminescence activity, the polymer also has aggregation-inducing luminescence properties and can be used for the detection of explosives, a...

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Abstract

The invention discloses a polyphenyltriazole formic acid ester and its preparation method and application. Using phenylpropiolic acid dibasic ester monomer and binary organic azide monomer as raw materials, in a polar aprotic solvent, Polymerization yields polyphenyltriazole formate. The reaction raw materials disclosed in the present invention are easy to obtain, and no by-products are generated during the polymerization reaction, which conforms to atom economy; the polymerization reaction has wide substrate applicability and good functional group compatibility, and can easily introduce various functional groups ; The polymerization reaction does not use a metal catalyst, which can eliminate the impact of catalyst residue on the biological and photoelectric properties of the polymer material. The polyphenyltriazole formate prepared by the invention has good processability, high thermal stability, degradability and aggregation-induced luminescent performance, and has potential applications in optical plastics, biomedical materials, fluorescence detection, etc. Value.

Description

Technical field [0001] The invention belongs to the fields of polymer chemistry and material science, and specifically relates to a polyphenyl triazole formate and a preparation method and application thereof. Background technique [0002] The development of new monomers and polymerization reactions are very important for polymer synthesis chemistry and the preparation of polymer functional materials. At present, most of the polymerization reactions are developed from organic small molecule reactions. The 1,3-dipolar cycloaddition reaction of acetylene compounds and organic azides to form 1,2,3-triazole compounds under heating conditions was reported as early as 1893. However, this reaction has not been widely used due to lack of regioselectivity and slow reaction rate. In 2002, Meldal in Denmark and Sharpless in the United States independently discovered that monovalent copper can catalyze the reaction of terminal alkynes with organic azide compounds, and only produce 1,4-disub...

Claims

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Application Information

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Patent Type & Authority Patents(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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