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Dendritic molecular organic fluorescent material, application thereof, fluorescent film and preparation method of fluorescent film

A fluorescent material and dendritic technology, applied in the field of fluorescent sensing, can solve the problems of poor stability, high toxicity of conjugated polymers, and low sensitivity, and achieve high efficiency, good photochemical stability, and high sensitivity

Active Publication Date: 2019-07-09
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Currently used for Fe 3+ , Hg 2+ and I - Fluorescent materials for sensing mainly include conjugated polymers, small molecule fluorescent materials, and polymer self-assembly materials, etc., but conjugated polymers are usually highly toxic and poorly stable, while small molecule fluorescent materials and polymer self-assembly materials are There is a disadvantage of low sensitivity

Method used

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  • Dendritic molecular organic fluorescent material, application thereof, fluorescent film and preparation method of fluorescent film
  • Dendritic molecular organic fluorescent material, application thereof, fluorescent film and preparation method of fluorescent film
  • Dendritic molecular organic fluorescent material, application thereof, fluorescent film and preparation method of fluorescent film

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preparation example Construction

[0063] The present invention has no special requirements for the synthesis method of the dendritic molecular organic fluorescent material described in the above scheme, and it is only necessary to use a method well known to those skilled in the art to synthesize the dendritic molecular organic fluorescent material that can obtain the above-mentioned structure. In the present invention , the preferred synthetic method comprises the following steps:

[0064] When n=1 in formula I, the synthetic method of described dendrimer organic fluorescent material preferably comprises the following steps:

[0065] (a) Under the action of an alkaline substance, make C-Br and bis-boronate carry out boronation reaction in an organic solvent to obtain a compound having a structure shown in Formula 1;

[0066]

[0067] (b) under nitrogen protection conditions, Br-B-I2, compound shown in formula 1, basic substance, palladium catalyst and organic solvent are mixed to carry out Suzuki reaction, ...

Embodiment 1

[0120]

[0121] The synthesis (denoted as G2) comprises the following steps:

[0122] (1) Synthesis of compound 9-(4-bromophenyl)-9H-carbazole

[0123]

[0124] Under nitrogen protection, carbazole (5g, 30mmol), p-fluorobromobenzene (10.47g, 60mmol), and cesium carbonate (21.5g, 62mmol) were added to a 250mL single-necked flask and mixed in DMSO (100mL) , reacted at 160°C for 48 hours, cooled to room temperature, extracted with dichloro / water solution, passed through the column with dichloromethane / petroleum ether, and dried in vacuo to obtain 7.7 g of white crystals with a yield of 80%.

[0125] 1 H NMR (500MHz, CDCl3) δ8.13 (d, J = 7.7Hz, 1H), 7.72 (d, J = 8.5Hz, 1H), 7.48–7.35 (m, 3H), 7.32–7.26 (m, 1H) .Mass spectrum molecular ion peak: 319.2, actual molecular weight: 322.2

[0126] (2) Synthesis of 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl)phenyl)-9H-carbazole (referred to as G1-Bn2)

[0127]

[0128] Under nitrogen protection, p-bromocarbazole (4g, 12.4mm...

Embodiment 2

[0147] (1) 1.1 mg of the dendrimer G2 prepared in Example 1 was dissolved in 0.35 mL of tetrahydrofuran to form 10 -3 mol / L dendrimer base solution, and then take 3 μL and place it in a quartz cuvette containing 3mL of the mixed solution (the volume ratio of tetrahydrofuran to water is 4:1), thereby obtaining 10 -6 mol / L dendrimer solution.

[0148] Record the ultraviolet absorption spectrum and the fluorescence emission spectrum of this dendrimer solution with a fluorescence spectrometer, and the obtained results are as follows: figure 1 As shown, the G2 mass spectrum was recorded with a matrix-assisted laser desorption time-of-flight mass spectrometer, and the obtained results are as follows figure 2 shown. according to figure 1 It can be seen that G2 has good optical properties, the band of about 394nm in the absorption spectrum comes from the pyrene nucleus, and the band of 301-350nm belongs to the absorption of carbazoles. Under excitation at 360nm, the PL spectrum G...

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Abstract

The invention provides a dendritic molecular organic fluorescent material, application thereof, a fluorescent film and a preparation method and application of the fluorescent film, and belongs to thefield of fluorescence sensing. The dendritic molecular organic fluorescent material provided by the invention has a structure shown as a formula I, wherein a unit A is used as a central core of a dendritic molecule; a unit B is a branched unit of the dendritic molecule; and a unit C is a peripheral active group of the dendritic molecule and has electrochemical activity. The dendritic molecular organic fluorescent material provided by the invention is accurate in molecular structure and good in repeatability, and has fluorescent response and colorimetric response to iodide ions, mercury ions and ferric ions at the same time; and according to the dendritic molecular organic fluorescent material and the fluorescent film prepared from the dendritic molecular organic fluorescent material provided by the invention, fluorescence / colorimetric dual-channel detection of iodide ions, mercury ions and ferric ions can be realized, the detection precision is high, and errors are small.

Description

technical field [0001] The invention relates to the technical field of fluorescent sensing, in particular to a dendrimer organic fluorescent material and its application, a fluorescent film and a preparation method thereof. Background technique [0002] The detection of heavy metals and halogens has always been a hot topic for scientists because they play an important role in natural ecosystems and human homeostasis. Among them, Fe 3+ , Hg 2+ and I - The detection of low concentrations has been continuously studied by scientists. [0003] Hg 2+ One of the most dangerous and ubiquitous pollutants, it is closely related to various functions of the body. Hg 2+ Not biodegradable, and can easily penetrate the skin, respiratory system and gastrointestinal tissue, so once Hg 2+ Absorbed, it accumulates and causes many diseases such as brain damage, cognitive and emotional disorders, kidney failure, Minamata disease, etc. [0004] I - As an important trace element in the hu...

Claims

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Application Information

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IPC IPC(8): C07D209/86C09K11/06C09D165/00C09D5/22C08G61/12
CPCC07D209/86C08G61/124C08G2261/11C08G2261/131C08G2261/312C08G2261/3142C08G2261/3241C08G2261/44C08G2261/522C08G2261/592C09D5/18C09D5/22C09D165/00C09K11/06C09K2211/1007C09K2211/1011C09K2211/1029
Inventor 张明张曌霞
Owner JILIN UNIV
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