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A boron compound containing four-coordinate octahydroxyquinoline and its preparation method and application

A hydroxyquinoline boron and four-coordination technology, which is applied in the field of four-coordination octahydroxyquinoline boron compound and its preparation, and achieves the effects of simple preparation process, low equipment requirements, and excellent solvent compatibility

Active Publication Date: 2020-11-17
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, under the action of external force, the reported mechanochromic materials can only show two color changes, such as changing from blue to green or green to yellow, but can achieve a wide range (blue to red). ) reports of fluorescent color transitions are still very rare
Moreover, the mechanochromic molecules that have been reported so far basically realize the force response by changing the position of the fluorescence emission wavelength through the change of the stacking method, while the mechanochromic materials based on the regulation of dual fluorescence have not been reported yet.

Method used

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  • A boron compound containing four-coordinate octahydroxyquinoline and its preparation method and application
  • A boron compound containing four-coordinate octahydroxyquinoline and its preparation method and application
  • A boron compound containing four-coordinate octahydroxyquinoline and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Preparation steps of the compound and its three polymorphs:

[0045] Step 1: Powder sample

[0046] Under an argon atmosphere, 0.4 g of short magnesium strips and 5 mL (1 mol / L) of iPr were added to a solution of 3.618 g of 4-hexylbromobenzene in 40 mL of anhydrous THF 2 NBH 2 , The reaction was stirred at 70° C. for 20 hours. After the reaction solution is cooled to room temperature, add 30 mL of 3 mol / L hydrochloric acid to the reaction solution under an ice bath, stir at room temperature for 45 minutes, then add water and ether to the reaction system, separate the layers, collect the organic phase, and extract the aqueous phase with dichloromethane Three times, the organic phases were combined, dried, filtered, and the solvent was removed by rotary evaporation. The obtained oily compound was dissolved in 15 mL of ether, 1.985 g of 5,7-diiodo-8-hydroxyquinoline was added to the solution, stirred at room temperature for 15 hours, a large amount of n-pentane was adde...

Embodiment 2

[0059] In this example, in the implementation step of the single ink color printing / writing process described in Example 1, the methyl tetrahydrofuran used is replaced with toluene with a boiling point greater than 85 degrees Celsius, and other steps are the same as in Example 1.

Embodiment 3

[0061] In this example, in the step of implementing the single ink color printing / writing process described in Example 1, the methyl tetrahydrofuran used is replaced with dimethylformamide (DMF) with a boiling point greater than 85 degrees Celsius, and other steps are the same as in Example 1 same.

[0062] In order to verify the benefits of the present invention, the basic photophysical properties, mechanochromic properties and single-ink color printing of the prepared compound and its three polymorphs were initially explored.

[0063] see figure 1 , are the UV-Vis absorption and fluorescence emission spectra of the compound in chloroform solution, in the figure a is the UV-Vis absorption spectrum, b is the fluorescence emission spectrum. It can be seen from the ultraviolet-visible absorption spectrum that there are three characteristic absorption bands, and all of them have large molar extinction coefficients, which proves that its absorption cross-section is large. It can...

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PUM

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Abstract

The invention discloses a tetra-coordinated octahydroxyquinoline boron compound, preparation method and application of the compound, belonging to the technical field of stimulus-response luminescent materials. Three single crystals of the compound can be obtained through different preparation methods, show double-fluorescence emission and have typical homogeneous polymorph property. After a solidsample of the compound is mechanically ground or subjected to external force, fluorescence light can be changed, and after the ground solid sample is subjected to heat treatment, the fluorescence light can be restored, so that high-efficiency restorable mechanophore property. The solution of the compound is heated to a certain temperature, is written / printed to paper, and can shown different fluorescence lights at room temperature, so that the creative application of color printing of single ink can be initially achieved. In conclusion, the compound has wide application prospects in the fieldsof color printing, anti-counterfeit materials, pressure sensors, optoelectronic devices and the like.

Description

technical field [0001] The invention belongs to the technical field of stimuli-responsive luminescent materials, and in particular relates to a boron compound containing four-coordinate octahydroxyquinoline and its preparation method and application. Background technique [0002] Intelligent color-changing materials that respond to external stimuli, such as mechanical force and heating, have attracted extensive research interest due to their potential application value in the fields of sensors, security inks, data storage, memory chips, and anti-counterfeiting labels. According to different stimulation methods, it can be divided into several types such as gas-induced, thermal-induced, photo-induced, electro-induced and newly developed mechanochromic materials. When stimulated by mechanical external force, such as grinding, stretching and pressing, the fluorescent properties (such as the color and intensity of light emission) of the material with mechanochromic properties wil...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K9/02C09D11/50C09D11/16C09D11/03
CPCC07B2200/13C07F5/027C09D11/03C09D11/16C09D11/50C09K9/02
Inventor 房喻祁彦宇徐文君丁南南尚丛娣刘科王朝龙
Owner SHAANXI NORMAL UNIV
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