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Free radical initiator, preparation method thereof, light-emitting free radical polymer and preparation method of light-emitting free radical polymer

A technology of free radicals and initiators, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of unreported free radical fluorescent polymers, difficult control of free radical content and spatial distribution, and achieve easy processing, Good mechanical properties, good film-forming performance

Pending Publication Date: 2021-12-31
THE CHINESE UNIV OF HONG KONG SHENZHEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, similar to physical doping methods, such random copolymerization methods lead to difficult control of the content and spatial distribution of free radicals in the polymer matrix
[0004] Radical fluorescent polymers that respond to temperature stimuli have not been reported yet

Method used

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  • Free radical initiator, preparation method thereof, light-emitting free radical polymer and preparation method of light-emitting free radical polymer
  • Free radical initiator, preparation method thereof, light-emitting free radical polymer and preparation method of light-emitting free radical polymer
  • Free radical initiator, preparation method thereof, light-emitting free radical polymer and preparation method of light-emitting free radical polymer

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preparation example Construction

[0072] The application also provides a preparation method of the free radical initiator, comprising:

[0073] a first reaction of the first compound with 3,4-dihydro-2H-pyran (THP) to obtain a second compound, and then a second reaction of the second compound with a trityl compound to obtain a third compound;

[0074] performing a de-THP protection reaction on the third compound to obtain a fourth compound, and then performing a dehydrogenation reaction on the fourth compound to obtain the free radical initiator;

[0075] The structural formula of the first compound is:

[0076]

[0077] The structural formula of the second compound is:

[0078]

[0079] The general structural formula of the third compound is:

[0080]

[0081] The general structural formula of the fourth compound is:

[0082]

[0083] Wherein, Y is a trityl group.

[0084] In order to better illustrate the above-mentioned trityl groups, an example is given: for example, when Y is a trichlorotr...

Embodiment 1

[0108] The present embodiment provides a kind of free radical initiator, and its structural formula is:

[0109]

[0110] Its preparation method is as follows:

[0111] step 1:

[0112]

[0113] Into a 50 mL round bottom flask was added the first compound CZ-OH (3.80 g, 10 mmol), p-toluenesulfonic acid monohydrate (1.52 g, 8 mmol) and 20 mL of tetrahydrofuran. 3,4-Dihydro-2H-pyran (2.74 mL, 30 mmol) was slowly added and stirred at room temperature for 1 hour. After the reaction was completed, saturated aqueous sodium bicarbonate solution was added for neutralization. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed by rotary evaporation. With petroleum ether: ethyl acetate=8:1 (volume ratio) as eluent, purify by column chromatography, obtain 2.74g (5mmol) white solid product, productive rate 50%, be the second compound (in the above equation Compound 1), its hydrogen spectrum is as figure 1 shown....

Embodiment 2

[0125] This embodiment provides a light-emitting free radical polymer, the general structural formula of which is:

[0126]

[0127] This embodiment also provides a preparation method of the above-mentioned light-emitting radical polymer, specifically as follows:

[0128] Under the protection of nitrogen atmosphere, add the free radical initiator (27mg, 0.03mmol) that embodiment 1 obtains in the Schlenk bottle after toasting through 20mL, catalyst stannous octoate Sn(Oct)2 (0.01mmol), monomer δ-valerolactone (300mg, 3mmol) and 5mL toluene, react at 130°C for 6 hours. The reaction system was cooled to room temperature, precipitated with methanol, and centrifuged. The solid was dissolved in a small amount of dichloromethane, and precipitated three times with methanol. The solid obtained by centrifugation was vacuum-dried to obtain a light green polymer with a yield of 70%. The relative number average molecular weight (n) is 9.7kg / mol, and the molecular weight distribution (w / ...

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Abstract

The invention provides a free radical initiator, a preparation method thereof, a light-emitting free radical polymer and a preparation method of the light-emitting free radical polymer. The structural formula of the free radical initiator is shown in the description. The preparation method of the free radical initiator comprises the following steps: reacting a first compound with 3, 4-dihydro-2H-pyran to obtain a second compound, and then reacting the second compound with a trityl compound to obtain a third compound; and carrying out THP protection removal reaction on the third compound to obtain a fourth compound, and carrying out dehydrogenation reaction on the fourth compound to obtain the free radical initiator. The polymer chain of the light-emittingfree radical polymer at least one free radical group. The preparation method of the light-emitting free radical polymer comprises the following step: reacting the free radical initiator with a monomeric compound to obtain the light-emitting free radical polymer with the temperature stimulation response characteristic. According to the free radical initiator provided by the invention, the aggregation-induced fluorescence quenching effect is inhibited by controlling the chain length of the polymer, and the critical response temperature of luminescence can be regulated and controlled by changing the chemical structure of the polymer chain.

Description

technical field [0001] The application relates to the field of new materials, in particular to a free radical initiator, a luminescent free radical polymer and a preparation method thereof. Background technique [0002] Free radicals are special organic materials containing unpaired electrons and open-shell electronic structures, and have broad application prospects in the field of organic optoelectronic devices. For example, organic light-emitting diodes based on free radical luminescent materials can theoretically achieve an internal quantum efficiency close to 100%. However, most of the free radical materials reported so far show aggregation-induced quenching (ACQ) effect when they are in the aggregated state, which leads to a significant decrease in luminous efficiency and a significant weakening of the sensitivity of sensor devices, thus limiting its large-scale practical application. [0003] In order to solve these problems, on the one hand, researchers have tried t...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06C08G63/08C08G63/87
CPCC07D209/86C09K11/06C08G63/08C08G63/87C09K2211/1466Y02P20/55
Inventor 王明锋侯丽曼
Owner THE CHINESE UNIV OF HONG KONG SHENZHEN
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