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A small organic molecule containing boron-nitrogen coordination bonds, its preparation method and its application to the sensing of fluoride ions

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

Active Publication Date: 2021-04-13
CHANGAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • A small organic molecule containing boron-nitrogen coordination bonds, its preparation method and its application to the sensing of fluoride ions
  • A small organic molecule containing boron-nitrogen coordination bonds, its preparation method and its application to the sensing of fluoride ions
  • A small organic molecule containing boron-nitrogen coordination bonds, its preparation method and its application to the sensing of fluoride ions

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Experimental program
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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 Image 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 a...

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Abstract

The invention discloses an organic small molecule containing a boron-nitrogen coordination bond, a preparation method and a sensing application to fluoride ions, and belongs to the technical field of preparation of fluorescent compounds and preparation of fluorescent probes. The present invention utilizes 2-(3-bromobenzothiophene)-2'-benzothiazole to react with n-butyllithium to generate a lithium reagent, and then reacts with triphenylboron to prepare a small molecule containing a boron-nitrogen coordination bond. It is verified by experiments that the small molecule containing the boron nitrogen (BN) coordination bond prepared by the present invention successfully realizes the selective recognition of fluoride ions. The preparation method of the boron-nitrogen (BN) coordination bond-containing fluorescent compound of the invention has the advantages of simple operation and mild reaction conditions, and the prepared fluorescent probe has the characteristics of photochemical stability, good selectivity and the like.

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 Patents(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