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Synthesis of metal-free, heavy-atom-free and long-lived room-temperature phosphorescent polymers by microwave irradiation

A technology of room temperature phosphorescence and microwave radiation, applied in chemical instruments and methods, luminescent materials, etc., can solve the problems of enhancement, toxicity, and increased material costs, and achieve strong phosphorescence emission, low price, and easy-to-obtain raw materials

Active Publication Date: 2022-04-26
FUJIAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ma Xiang and others found (Chinese patents CN107056982A, CN106118631A, CN106188391B, CN109306034A) to combine polymer monomers with heavy atom (mainly bromine) functional groups or aromatic rings with oxygen-containing functional groups and double bonds with acrylamide through free The pure organic room-temperature phosphorescent polymer material is prepared by the polymerization of polyacrylamide, and the non-radiative relaxation of the triplet state of the carbonyl functional group is suppressed by the hydrogen bond network of polyacrylamide. At the same time, the hydrogen bond network maintains the heavy atom effect between the bromine atom and the carbonyl group, and enhances the The phosphorescence emission ability of the carbonyl functional group enables it to emit strong phosphorescence at room temperature. Some of the monomers in the invention contain halogen heavy atoms. The existence of heavy atoms will increase the cost of the material and is relatively toxic.

Method used

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  • Synthesis of metal-free, heavy-atom-free and long-lived room-temperature phosphorescent polymers by microwave irradiation
  • Synthesis of metal-free, heavy-atom-free and long-lived room-temperature phosphorescent polymers by microwave irradiation
  • Synthesis of metal-free, heavy-atom-free and long-lived room-temperature phosphorescent polymers by microwave irradiation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Dissolve 50 mg (0.26 mmol) of vinyl carbazole and 1.38 g (19.5 mmol) of acrylamide in 23 g of water in a round bottom flask, then add 0.014 g of ammonium persulfate, mix well and place in a WBFY201 microwave reactor ( 2450 ± 50 MHz microwave frequency) and connected to a straight condenser, reflux the copolymerization reaction at 520 W microwave output power for 4 min, after cooling to room temperature, drop the reaction solution into methanol to precipitate, filter, wash the filter with methanol The cake was dried three times in a vacuum oven at 70°C to obtain a metal-free, heavy-atom-free, long-lived phosphorescent polymer material at room temperature. The phosphorescent emission peaks are located at 414 nm, 440 nm and 462 nm. figure 1 As shown, the triplet lifetimes are 3.22 s, 3.24 s and 3.21 s, respectively.

[0021] The long-life room temperature phosphorescent polymer prepared in this example emits blue-violet light under the irradiation of a 365 nm ultraviolet l...

Embodiment 2

[0023] Dissolve 50 mg (0.26 mmol) of vinyl carbazole and 460 mg (6.48 mmol) of acrylamide in 8.5 g of water in a round bottom flask, then add 0.005 g of ammonium persulfate, mix well and place in a WBFY201 microwave reactor ( 2450 ± 50MHz microwave frequency) and connected to a straight condenser, reflux copolymerization reaction at 520W microwave output power for 3.5 minutes, after cooling to room temperature, drop the reaction liquid into methanol to precipitate, filter, and wash the filter cake with methanol 3 The second time, it was dried in a vacuum drying oven at 80°C to obtain a microwave-assisted synthesis of metal-free, heavy-atom-free, long-lived room temperature phosphorescent polymer. Its phosphorescent emission peaks are located at 414 nm, 440 nm and 462 nm, and the triplet lifetimes are 4.06 s, 3.89 s and 3.96 s, respectively. The lifetime decay diagram is shown in figure 2 .

[0024] The organic room-temperature phosphorescent material prepared in this example...

Embodiment 3

[0026] Dissolve 50 mg (0.26 mmol) of vinyl carbazole and 1.38 g (19.5 mmol) of acrylamide in 22 g of N,N-dimethylformamide in a round bottom flask, then add 0.018 g of ammonium persulfate, and mix well Placed in a WBFY201 microwave reactor (2450 ± 50 MHz microwave frequency) and connected to a straight condenser, reflux copolymerization reaction at 325 W microwave output power for 6 minutes, after cooling to room temperature, drop the reaction liquid into methanol to precipitate , filtered, washed the filter cake with methanol for 3 times, and dried in a vacuum oven at 80°C to obtain a metal-free, heavy-atom-free, long-life room-temperature phosphorescent polymer material, which emits blue-violet light under a 365 nm ultraviolet lamp. After the UV lamp was turned off, the afterglow time reached 2 s.

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Abstract

The invention relates to a method for synthesizing metal-free, heavy-atom-free and long-life room-temperature phosphorescent polymers through microwave radiation. The method is to prepare a long-lived room temperature phosphorescent polymer material through free radical copolymerization of vinyl carbazole and acrylamide monomer under the action of microwaves. The phosphorescent life is long at room temperature, and the raw materials are easily available. The preparation method is simple and convenient, and the reaction time is short. , the product is non-toxic, non-polluting, heavy metal-free, halogen-free, good water solubility, and has a wide range of application prospects.

Description

technical field [0001] The invention relates to a method for synthesizing metal-free, heavy-atom-free and long-life room-temperature phosphorescent polymers by microwave radiation, which belongs to the field of organic light-emitting materials. Background technique [0002] Room-temperature phosphorescent materials with the advantages of high quantum yield, large Stokes shift, and long lifetime have important application value in the fields of biological imaging, chemical sensors, and optoelectronics. At present, most room-temperature phosphorescent materials are inorganic compounds, metal-organic complexes and pure organic compounds. Since inorganic compound phosphorescent materials are mainly prepared by high-temperature solid-phase method, sol-gel method and other high-temperature methods, the conditions are relatively harsh, and organometallic complexes are mainly noble metal complexes such as iridium, platinum, osmium, and europium. Resources are scarce, expensive and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F220/56C08F226/12C08F2/46C09K11/06
CPCC08F220/56C08F2/46C09K11/06C09K2211/1466C08F226/12
Inventor 张语珊林美娟
Owner FUJIAN NORMAL UNIV
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