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Piezochromic tetraphenylethylene compound as well as preparation method and application thereof

A tetraphenylethylene and piezochromic technology, applied in the field of fluorescent materials, can solve the problems of unusual emission phenomenon of TPE-based polymers, complex synthesis process, harsh synthesis conditions, etc., achieve strong molecular aggregation-induced luminescent effect, and improve reaction efficiency , color sensitive effect

Pending Publication Date: 2021-08-27
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Substituents on aromatic rings affect intramolecular rotation, leading to unusual emission phenomena in TPE-based polymers
[0006] However, the synthesis process of tetraphenylethylene piezochromic materials reported so far is complex, time-consuming, and the synthesis conditions are harsh. Therefore, more piezochromic materials with simple processes need to be developed.

Method used

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  • Piezochromic tetraphenylethylene compound as well as preparation method and application thereof
  • Piezochromic tetraphenylethylene compound as well as preparation method and application thereof
  • Piezochromic tetraphenylethylene compound as well as preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0029] This embodiment provides a method for preparing tetrastyryl cis-position diether, which specifically includes the following steps:

[0030] Step a, add 10.2g (40mmol) pinacol diborate and 0.25g (0.2mmol) tetrakistriphenylphosphine platinum into a dry reaction vessel containing 50ml N,N-dimethylformamide and nitrogen gas , then dissolve 3.6g (20mmol) toluene in 50ml N,N-dimethylformamide to form a solution, drop it into the above reaction vessel, raise the temperature to 90°C, react at 90°C for 9h, and cool to Room temperature, rotary evaporation under reduced pressure to obtain the crude product solution of distyryl borate pinacol ester, after column chromatography (stationary phase is silica gel) with petroleum ether: dichloromethane = 2:1 as the eluent, the washing The solvent was removed by rotary evaporation under reduced pressure to obtain 5.95 g of white needle-like solid, that is, refined distyrylboronic acid pinacol ester, with a yield of 85% and a purity of 98%...

Embodiment 2

[0040] This embodiment provides a preparation method of tetrastyryl dimethyl, which specifically includes the following steps:

[0041] Step a, add 10.2g (40mmol) pinacol diborate and 0.25g (0.2mmol) tetrakistriphenylphosphine platinum into a dry reaction vessel containing 50ml N,N-dimethylformamide and nitrogen gas , then dissolve 3.6g (20mmol) toluene in 50ml N,N-dimethylformamide to make a solution, drop it into the above reaction vessel, raise the temperature to 85°C, react at 85°C for 9.5h, cool to room temperature, rotary evaporation under reduced pressure to obtain the crude product solution of distyryl borate pinacol ester, after column chromatography (stationary phase is silica gel) with petroleum ether: dichloromethane = 2:1 as the eluent, the The solvent was removed from the eluate by rotary evaporation under reduced pressure to obtain 5.6 g of white needle-like solid with a yield of 80%.

[0042] Step b, take 3.50g (10mmol) refined distyrylboronic acid pinacol est...

Embodiment 3

[0051] This embodiment provides a kind of preparation method of tetrastyryl cis-position diester, specifically comprises the following steps:

[0052] Step a, add 10.2g (40mmol) pinacol diborate and 0.25g (0.2mmol) tetrakistriphenylphosphine platinum into a dry reaction vessel containing 50ml N,N-dimethylformamide and nitrogen gas , then dissolve 3.6g (20mmol) toluene in 50ml N,N-dimethylformamide to make a solution, drop it into the above reaction vessel, raise the temperature to 70°C, react at 70°C for 10h, and cool to Room temperature, rotary evaporation under reduced pressure to obtain the crude product of distyrylboronic acid pinacol ester, after column chromatography (stationary phase is silica gel) with petroleum ether: dichloromethane = 2:1 as the eluent, the eluted The solvent was removed by rotary evaporation under reduced pressure to obtain 4.9 g of white needle-like solid with a yield of 70%.

[0053] Step b, take 2.43g (6.94mmol) refined distyrylboronic acid pina...

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Abstract

The invention relates to the technical field of fluorescent materials, in particular to a piezochromic tetraphenylethylene compound as well as a preparation method and application thereof. The tetraphenylethylene-based compound has excellent piezochromism and molecular aggregation-induced fluorescence, can change color without solvent fumigation and heating, and has a rapid recovery property. The preparation method comprises the following steps: reacting diphenylacetylene with bis (pinacolato) diboron to prepare stilbene (pinacolato) diboron, and reacting with a p-bromobenzene substituent to obtain a final product. Due to the piezo-chromic effect and the rapid recovery property of the piezo-chromic tetraphenylethylene compound, the piezo-chromic tetraphenylethylene compound can be applied to preparation of piezo-chromic materials at room temperature and is further applied to the fields of brain tumor imaging technologies, near-infrared probe technologies, photoelectric devices and the like.

Description

technical field [0001] The invention belongs to the technical field of fluorescent materials, and in particular relates to a piezochromic tetrastyryl compound and a preparation method and application thereof. Background technique [0002] Conventional organic dyes are quenched at high concentrations, and this aggregation quenching (ACQ) effect limits their applications. Based on the limitation of intramolecular motion (RIM) mechanism, novel piezofluorochromic (MFC) materials with aggregation-induced emission (AIE) phenomenon overcome the shortcomings of ACQ. [0003] MFC materials have great application prospects in information security, memory devices, sensors, and fluorescent switches due to their unique molecular aggregation-induced luminescence, high luminous efficiency, mechanochromism, and solvent discoloration. As a new type of smart material, this type of material will respond to its chromophore with the increase of mechanical force such as grinding and pressing, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/215C07C41/30C07F5/02C07C15/52C07C1/32C07C69/78C07C67/343C07C255/51C07C253/30C07C205/06C07C201/12C09K9/02
CPCC07C43/215C07C41/30C07F5/025C07C15/52C07C1/321C07C69/78C07C67/343C07C255/51C07C253/30C07C205/06C07C201/12C09K9/02C09K2211/1007
Inventor 赵雄燕曹玉清王鑫
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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