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Organic small molecule containing boron-nitrogen coordination bond, and preparation method and sensing application thereof to fluorine ion

A technology of coordination bonds and small molecules, applied in the field of small organic molecules and their preparation, can solve the problems of low fluorescence luminescence efficiency of fluoride ion probe materials, low fluoride ion response value, poor fluorine ion selectivity, etc., to achieve Photochemical stability, easy operation, good selectivity

Active Publication Date: 2019-04-12
CHANGAN UNIV
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Problems solved by technology

[0006] It can be seen that the conjugated system containing boron nitrogen (BN) has excellent performance and great development prospects, but the fluorescence luminescence efficiency of many reported fluoride ion probe materials is not high, the response value to fluoride ion is low and in many The selectivity to fluoride ion in the anion is also not good
There are still many difficulties in realizing the efficient and simple design and synthesis of boron nitrogen (BN) compounds

Method used

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  • Organic small molecule containing boron-nitrogen coordination bond, and preparation method and sensing application thereof to fluorine ion
  • Organic small molecule containing boron-nitrogen coordination bond, and preparation method and sensing application thereof to fluorine ion
  • Organic small molecule containing boron-nitrogen coordination bond, and preparation method and sensing application thereof to fluorine ion

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preparation example Construction

[0039] 2. Preparation of fluorescent probes

[0040] 1) Dissolve the fluorescent compound in tetrahydrofuran to prepare 1×10 -3 stock solution of M;

[0041] 2) Add 4950 μL tetrahydrofuran to every 50 μL stock solution, and leave it at room temperature for 2 hours to prepare the fluorescent probe.

[0042] For detection: use 1.0M tetrabutylammonium fluoride tetrahydrofuran solution to prepare 1×10 -3 M is the solution of fluoride ion to be measured.

Embodiment 1

[0044] Under argon protection, compound 1 (0.478g, 1.38mmol) was dissolved in absolute anhydrous THF (10mL), and n-butyllithium (0.56mL, 2.5M in hexane, 1.38mmol) was added dropwise at -78°C , kept for 1h after the dropwise addition, dissolved triphenylboron (0.388g, 1.6mmol) in absolute anhydrous THF (10mL), gradually added dropwise to the above solution under the protection of argon, then warmed up to room temperature, continued The reaction was stirred for 12 h, the solvent was removed under reduced pressure, and a yellow solid was obtained by separation and purification on a silica gel column, the yield: 35%.

[0045] The H NMR spectrum of the obtained product is as Figure 6 As shown, the carbon NMR spectrum is as Figure 7 shown.

[0046] In order to verify the effect of the present invention, the detection of fluoride ions by the boron nitrogen compound synthesized in Example 1 was explored, as shown in the figure.

[0047] in, figure 1 , figure 2 is the UV-visible ...

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Abstract

The invention discloses a organic small molecule containing a boron-nitrogen coordination bond, and a preparation method and sensing application thereof to a fluorine ion, and belongs to the technicalfield of preparation of fluorescent compounds and preparation of fluorescent probes. According to the invention, 2-(3-bromobenzothiophen-2-yl)benzothiazole reacts with n-butyl lithium to form a lithium reagent, and then the lithium reagent reacts with triphenylboron to prepare the small molecule containing the boron-nitrogen coordination bond. Experiments verify that the small molecule containingthe boron-nitrogen (BN) coordination bond prepared by the invention can successfully realize selective recognition of the fluorine ion. The preparation method of the fluorescent compound containing the boron-nitrogen (BN) coordination bond of the invention is simple and convenient, the reaction condition is mild, and a prepared fluorescent probe has the characteristics of photochemical stabilityand good selectivity.

Description

technical field [0001] The invention belongs to the technical field of preparation of fluorescent compounds and fluorescent probes thereof, and specifically relates to a small organic molecule containing a boron-nitrogen coordination bond, a preparation method thereof and a sensing application to fluoride ions. Background technique [0002] Organic optoelectronics is a new interdisciplinary subject across chemistry, physics, materials and information, which has attracted extensive attention from academia and industry in recent years. So far, many organic optoelectronic devices such as organic light-emitting diodes (OLEDs), organic field-effect transistors (OFETs), organic photovoltaic cells (OPVs) and organic sensors have shown incomparable advantages over inorganic non-metallic devices. [0003] In recent years, the impact of fluoride ions on humans has been increasing, because contact with fluoride ions is unavoidable in our daily life, such as ointments we use for cleanin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/027C09K11/06C09K2211/1007C09K2211/1014C09K2211/1037C09K2211/1092G01N21/6428G01N2021/6432
Inventor 晏妮何刚张维东王之君
Owner CHANGAN UNIV
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