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A class of borazine benzothiophene derivatives, conjugated high molecular polymers and their preparation methods and application of fluoride ion detection

A technology of thiophene derivatives and conjugated polymers, which is applied in the fields of conjugated polymers and their preparation, fluoride ion detection applications, borazine benzothiophene derivatives, and can solve problems such as hindering thiophene borazine heterocycles

Active Publication Date: 2021-09-07
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, reports on the selective late functionalization of thiophene boron nitrogen molecules are still rare. Although bromination reactions can be used to modify chemical sites of thiophene boron nitrogen molecules, such modifications often occur at fixed chemical sites. , which to some extent hinders the development of selective late functionalization of thiophene borazine heterocycles

Method used

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  • A class of borazine benzothiophene derivatives, conjugated high molecular polymers and their preparation methods and application of fluoride ion detection
  • A class of borazine benzothiophene derivatives, conjugated high molecular polymers and their preparation methods and application of fluoride ion detection
  • A class of borazine benzothiophene derivatives, conjugated high molecular polymers and their preparation methods and application of fluoride ion detection

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Embodiment 1

[0145] 1. The borazine benzothiophene small molecule and conjugated polymer described in the present invention are prepared through the following steps:

[0146] 1) Preparation of compound 2a or compound 2b

[0147] Under the protection of an inert gas, 3-bromo-2,2'-bithiophene (2.45g, 10mmol), aniline / 4-hexylaniline (11mmol), sodium tert-butoxide (1.16g, 12.10mmol), three (di Benzylideneacetone) dipalladium (293mg, 0.32mmol) and tri-tert-butylphosphine tetrafluoroborate (153.75mg, 0.53mmol) were dissolved in absolute anhydrous toluene (20mL) to obtain a reactant system; React at 100°C for 20 h, remove the solvent under reduced pressure, and separate through the column to obtain the target compound 2a or compound 2b. The reaction equation is as follows:

[0148]

[0149] 2) Preparation of compound 3a or compound 3b

[0150] Under the protection of an inert gas, the compound 2a / compound 2b (5mmol) prepared in step 1), triethylamine (1.14g, 11.25mmol), dichlorophenylborane...

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Abstract

The invention discloses a class of borazine benzothiophene derivatives, a conjugated polymer, a preparation method thereof and a fluoride ion detection application, and belongs to the technical field of preparation of fluorescent compounds and fluorescent probes. The BNDT derivatives disclosed in the present invention are developed by using the introduction of BN units to cause differences in the activity of the bithiophene chemical sites. Based on different reaction intermediates (brominated and boronate grouped products), the present invention is easy to operate 1. The borazine benzothiophene small molecule and polymer were successfully synthesized by a method with mild reaction conditions, which is of great significance for the selective late functionalization of borazine heterocycles and the design and synthesis of new optoelectronic materials. The present invention successfully realizes the selective late functionalization of borazine benzothiophene small molecules through different cross-coupling reactions, and develops a series of BNDT derivatives. The exploration of such BNDT derivatives has further enriched the types of fluorescent probes for fluoride ion detection and promoted the development of new chemical sensing.

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 class of borazine benzothiophene derivatives, conjugated high molecular polymers, preparation methods thereof, and fluoride ion detection applications. Background technique [0002] Due to the inherent electron-deficient nature of boron atoms in the third main group, boron-containing p-π conjugated polycyclic aromatic hydrocarbons (PAHs) have attracted extensive attention as ideal electron acceptor materials, but they have high Antiaromatic, extremely sensitive to water and oxygen, and there are still many difficulties in synthesizing boron-containing compounds with stable properties. A large number of studies have shown that the formation of boron-nitrogen bonds (BN) can not only stabilize boron atoms, but also effectively regulate the energy levels and intermolecular interactions of conjugated molecules. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06C08G61/12G01N21/64
Inventor 何刚张思坤赵永涛初大可
Owner XI AN JIAOTONG UNIV
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