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Hybrid tetra-aryl ethylene compound, polymer and preparation method and application thereof

A tetraarylene compound technology, applied in the field of hybrid tetraarylene polymers and its preparation, can solve the problems of reducing the overall performance of molecules, cumbersome synthesis methods, complex chemical structures, etc., and achieve good photochromic performance, The effect of wide application field and sensitive photoresponse

Active Publication Date: 2017-08-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, sometimes different fragment building blocks interact with each other, reducing the overall performance of the molecule
It is also very important that the chemical structure of these compounds is generally very complicated, and the molecular structure is very large, so that the synthetic route is very long, the synthetic method is very loaded down with trivial details, and the yield is very low

Method used

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  • Hybrid tetra-aryl ethylene compound, polymer and preparation method and application thereof
  • Hybrid tetra-aryl ethylene compound, polymer and preparation method and application thereof
  • Hybrid tetra-aryl ethylene compound, polymer and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The preparation of embodiment 1 compound a and b

[0060] Synthetic routes of compounds a and b

[0061]

[0062] Synthesis of Intermediate A1

[0063] Under the protection of argon, weigh AlCl 3 (2.67g, 20mmol) in a round bottom flask, add 20mL of carbon disulfide to it, keep stirring at 25°C for 10min, add 2,5-dimethylthiophene (1.12g, 10mmol), and benzoyl chloride (1.40g, 10mmol) to heat up Reflux and stir the reaction for 6h, pour the reaction solution into 2N hydrochloric acid, extract 3 times with dichloromethane, dry over anhydrous sodium sulfate, concentrate, and separate by column chromatography to obtain a brown oily liquid, namely intermediate A1 (1.6g, yield rate of 74%).

[0064] Synthesis of compounds a and b

[0065] Under the protection of argon, weigh zinc powder (1.25g, 19mmol) in the reaction flask, under the protection of nitrogen, add 20mL of anhydrous tetrahydrofuran, cool down to -15°C, add TiCl dropwise 4 (1.5mL), after the dropwise addit...

Embodiment 2

[0068] The preparation of embodiment 2 compound c and d

[0069] Synthetic routes of compounds c and d

[0070]

[0071] Synthesis of Intermediate A2

[0072] Under the protection of argon, weigh AlCl 3 (2.67g, 20mmol) in a round bottom flask, add carbon disulfide 20mL to it, keep stirring at 25°C for 10min, add 2-methyl-5-phenylthiophene (1.74g, 10mmol), benzoyl chloride (1.40g, 10mmol ) was heated and refluxed and stirred for 6h, the reaction solution was poured into 2N hydrochloric acid, extracted 3 times with dichloromethane, dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography to obtain a brown oily liquid, i.e. intermediate A2 (1.9g , yield 68%).

[0073] Synthesis of compounds c and d

[0074] Under the protection of argon, weigh zinc powder (1.25g, 19mmol) in a round bottom flask, under nitrogen protection, add 20mL of tetrahydrofuran, cool down to -15°C, add TiCl dropwise 4 (1.5mL), the dropwise addition was completed, kept...

Embodiment 3

[0077] The preparation of embodiment 3 compound e

[0078] Synthetic route of compound e

[0079]

[0080] Synthesis of Intermediate A3

[0081] Under the protection of argon, weigh AlCl 3 (2.64g, 20mmol) and a round bottom flask, add carbon disulfide 20mL to it, keep stirring at 25°C for 10min, add 2-methyl-5-chlorothiophene (1.32g, 10mmol), benzoyl chloride (1.40g, 10mmol) The temperature was raised to reflux and stirred for 6 hours, the reaction solution was poured into 2N hydrochloric acid, extracted several times with dichloromethane, dried over anhydrous sodium sulfate, concentrated, and column chromatography gave a brown oily liquid, namely intermediate A3 (1.7g, collected rate of 72%).

[0082] Synthesis of compound e

[0083] Under the protection of argon, weigh zinc powder (1.25g, 19mmol) in a round bottom flask, under nitrogen protection, add 20mL of tetrahydrofuran, cool down to -15°C, add TiCl dropwise 4 (1.5mL), after the dropwise addition, keep at -15°C fo...

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PUM

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Abstract

The invention discloses a hybrid tetra-aryl ethylene compound. The structure of the hybrid tetra-aryl ethylene compound is as shown in the specification, wherein, Ar1 is phenyl or hexahydric heteroaryl; Ar2 and Ar3 are phenyl, hexahydric heteroaryl or quinary heteroaryl independently and respectively; X is nitrogen, oxygen, sulphur or silicon; R1, R2 and R3 are hydrogen, fluorine, chorine, bromine, iodine, methyl, ethyl, propyl, isopropyl, normal-butyl, isobutyl, tertiary butyl, methoxy, ethyoxyl, amino, hydroxyl, carboxyl, nitryl, sulfonic acid group, trifluoromethyl, phenyl, benzyl, benzoyl, para-bromophenyl, para-fluorophenyl, thiophene, pyridine, or crown ether. The invention further discloses a preparation method of the hybrid tetra-aryl ethylene compound and an application thereof, and discloses a polymer of the hybrid tetra-aryl ethylene compound, a preparation method and an application thereof. The hybrid tetra-aryl ethylene compound is unique in structure performance; the compound has good photochromic performance as well as excellent aggregation-induced emission performance.

Description

technical field [0001] The present invention relates to the technical field of organic optical material compounds, in particular to a hybrid tetraarylethene compound with photochromic and aggregation-induced luminescent properties and its preparation method and application, and a hybrid tetraarylene polymer and its preparation Methods and applications. Background technique [0002] The 21st century is the century of new materials. Nowadays, the development of organic light-emitting and color-changing functional materials is changing with each passing day, and the demand for their applications is also increasing. Therefore, the structural design and research of various color-changing and luminescent materials are flourishing. In recent years, we have been paying attention to the preparation and performance research of diarylene color-changing materials, and we have also made a lot of explorations on the performance development and structure design of tetraarylene. We know ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/08C07D333/12C07D409/14C07D307/36C09K9/02C09K11/06C08G61/02
CPCC07D307/36C07D333/08C07D333/12C07D409/14C08G61/02C08G2261/145C08G2261/226C08G2261/312C08G2261/3223C08G2261/3327C08G2261/411C08G2261/522C09K9/02C09K11/06C09K2211/1029C09K2211/1088C09K2211/1092
Inventor 罗千福曹飞王朝霞窦清玉谭贤志李文杰金飘飘
Owner EAST CHINA UNIV OF SCI & TECH
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