A conjugated microporous carbazole polymer, its preparation method and application, and a fluorescent film and its preparation method

A technology of conjugated micropores and polymers, used in fluorescence/phosphorescence, material analysis by optical means, instruments, etc., to achieve the effects of good stability, high selectivity, and strong fluorescence quenching effect

Active Publication Date: 2022-04-12
TAIZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few CMPs that can be applied to the detection of nitro explosives at present, therefore, it is urgent to develop new porous materials for the rapid detection of nitro explosives

Method used

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  • A conjugated microporous carbazole polymer, its preparation method and application, and a fluorescent film and its preparation method
  • A conjugated microporous carbazole polymer, its preparation method and application, and a fluorescent film and its preparation method
  • A conjugated microporous carbazole polymer, its preparation method and application, and a fluorescent film and its preparation method

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preparation example Construction

[0046] The present invention provides a method for preparing a conjugated microporous carbazole polymer described in the above scheme, comprising the following steps:

[0047] Under the action of an oxidizing agent, 1,3,6,8-tetrakis(4-(9H-carbazol-9-yl)phenylpyrene (L) is oxidatively polymerized in an organic solvent to obtain a compound having the structure shown in formula I The conjugated microporous carbazole polymer (referred to as CK-CMP).

[0048] In the present invention, the equation of the oxidative polymerization reaction is shown in formula II:

[0049]

[0050] In the present invention, the 1,3,6,8-tetrakis(4-(9H-carbazol-9-yl)phenylpyrene is preferably prepared by the following steps:

[0051] Suizik coupling reaction of 1,3,6,8-tetrabromopyrene, 4-(9H-carbazol-9-yl)phenylboronic acid, basic substance and palladium catalyst in a solvent gives 1,3,6, 8-Tetrakis(4-(9H-carbazol-9-yl)phenylpyrene.

[0052] In the present invention, the alkaline substance prefer...

Embodiment 1

[0088] (1) Preparation of 1,3,6,8-tetrakis(4-(9H-carbazol-9-yl)phenylpyrene (L)

[0089] Add 1,3,6,8-tetrabromopyrene (1.0356g, 2mmol), 4-(9H-carbazol-9-yl)phenylboronic acid (2.8712g, 10mmol) and potassium carbonate in a 250mL three-neck round bottom flask (3.15g, 23mmol), Pd(PPh 3 ) 4 (0.6g, 0.50mmol), dioxane 100mL and 10mL distilled water, this system is in N 2 The reaction was stirred at 100°C for 3 days in the atmosphere. After the reaction, the yellow reaction mixture was cooled to room temperature, transferred to dilute hydrochloric acid solution (100 mL), filtered and washed with water (3×40 mL). After the filter cake was dried, it was washed with CHCl 2 Carry out Soxhlet extraction for 48h, CHCl 2 The extract was evaporated under reduced pressure, and the obtained crude product L was further purified by silica gel column chromatography to obtain 0.5 g of a bright yellow solid (yield 22%)

[0090] The proton spectrum data of gained product is:

[0091] 1HNMR (4...

Embodiment 2

[0137] Other conditions are consistent with Example 1, only the consumption of monomer L in step (2) is changed to 0.6mmol, the oxidizing agent is changed to ammonium persulfate, and polymer CK-CMP, CK-CMP suspension, and CK-CMP are prepared respectively. CMP fluorescent film.

[0138] Physical characterization and fluorescent performance tests were performed on CK-CMP, CK-CMP suspension and CK-CMP fluorescent film according to the above method, and the test results were similar to those in Example 1.

[0139] According to the above examples, it can be seen that the present invention successfully synthesized the oxidative self-polymerization of 1,3,6,8-tetrakis(4-(9H-carbazol-9-yl)phenyl)pyrene (L) by oxidizing agent The conjugated microporous carbazole polymer as the core, especially the introduction of pyrene in the three-dimensional framework, makes the polymer exhibit strong luminescent properties in various polar solvents under ultraviolet light irradiation; and the polym...

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Abstract

The invention relates to the field of polymer materials, and provides a conjugated microporous carbazole polymer, a preparation method and application thereof, a fluorescent film and a preparation method thereof. In the present invention, 1,3,6,8-tetrakis(4-(9H-carbazole-9-yl)phenylpyrene is oxidatively self-polymerized under the induction of an oxidant to obtain a conjugated microporous carbazole polymer. The polymerization The polymer has good thermal stability and small pore size, and because the structure of the polymer includes pyrene units, it can exhibit strong luminescence under ultraviolet light irradiation, and the polymer has a very high resistance to PA Selectivity and sensitivity, PA can be detected by fluorescence quenching method; the polymer is made into a fluorescent film and applied to the detection of nitro explosives, which can make the detection more convenient and easy to implement; and as a conjugated Polymers, which also have broad application prospects in the fields of photovoltaic cells, cell imaging, and photocatalysis.

Description

technical field [0001] The invention relates to the technical field of polymer materials, in particular to a conjugated microporous carbazole polymer, a preparation method and application thereof, a fluorescent film and a preparation method thereof. Background technique [0002] Because it is closely related to national security, people's safety and environmental protection, the detection of nitro explosives has become an important research field. As a highly explosive and dangerous energy source, nitro explosives can be used as common materials for explosive devices. Because it is often used in fireworks, leather, dyes and other industries, it will flow into the soil, rivers and lakes, causing serious pollution. health and environmental issues. Among these compound materials with high energy, chemical sensing of 2,4,6-trinitrophenol (PA) or 2,4,6-trinitrotoluene (TNT) is especially required because they are Concentrations are still highly explosive and toxic. However, tr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C08L65/00C08J5/18G01N21/64
CPCC08G61/124C08J5/18G01N21/643G01N2021/6432C08J2365/00C08G2261/11C08G2261/18C08G2261/3241C08G2261/43C08G2261/522
Inventor 任世斌李培贤吴建波韩得满
Owner TAIZHOU UNIV
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