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Photochromic bis(N-ethyl-1,8-naphthalimide)amine-benzothiophene hybrid type perfluorocyclopentene compound, and synthetic method and application thereof

A perfluorocyclopentene, photochromic technology, applied in chemical instruments and methods, color-changing fluorescent materials, luminescent materials, etc., to achieve the effect of broad application prospects

Inactive Publication Date: 2015-02-04
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, so far, bis(N-ethyl-1,8-naphthalimide) amine-benzothiophene mixed-type perfluorocyclopentene compounds have not yet seen any literature and patent reports

Method used

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  • Photochromic bis(N-ethyl-1,8-naphthalimide)amine-benzothiophene hybrid type perfluorocyclopentene compound, and synthetic method and application thereof
  • Photochromic bis(N-ethyl-1,8-naphthalimide)amine-benzothiophene hybrid type perfluorocyclopentene compound, and synthetic method and application thereof
  • Photochromic bis(N-ethyl-1,8-naphthalimide)amine-benzothiophene hybrid type perfluorocyclopentene compound, and synthetic method and application thereof

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Embodiment Construction

[0025] The name is: 1-(2-dimethyl-3-benzothienyl), {2-[2-methyl-5-(4-((bis(N-ethyl-1,8-naphthoylidene) Amine)amine)methyl)-phenyl)]-3-thienyl}perfluorocyclopentene, the structural formula is as follows:

[0026]

[0027] The synthetic scheme Scheme 1 of this novel diaryl perfluorocyclopentene photochromic compound is shown in:

[0028] Scheme1:

[0029] Its specific synthetic steps are as follows:

[0030] 1. 1-(2-Methylbenzothiophen-1-yl) perfluorocyclopentene (3):

[0031] Dissolve compound 2 (3.0g, 13.5mmol) in 60 ml THF, stir under nitrogen and -78°C, slowly inject 2.5 mol / L n-BuLi (5.9ml, 14.9mmol), and continue stirring at low temperature for half an hour . Inject perfluorocyclopentene (2 mL, 14.9 mmol) into the reaction flask, continue to stir the reaction mixture at low temperature for 1 h, then naturally rise to room temperature, add an appropriate amount of water to terminate the reaction, separate the layers and extract with ether, combine the organic phas...

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Abstract

The invention discloses a photochromic bis(N-ethyl-1,8-naphthalimide)amine-benzothiophene hybrid type perfluorocyclopentene compound, and a synthetic method and application thereof. The photochromic material keeps good photochromic performance in solutions, and has extremely good chemical and heat stability, extremely good sensitivity and other superior performances when being in a ring-opened state (a colorless state) and a ring-closed state (a color appearance state), is applicable to fluorescence detection, fluorescence-controlled switches, high-density holographic optical storage, dual-control fluorescence molecule switches, pH chemical sensors, metal ion chemical sensors and the like, and is wide in application prospect.

Description

technical field [0001] The invention relates to a photochromic bis(N-ethyl-1,8-naphthoimide)amine-benzothiophene mixed type perfluorocyclopentene compound, a synthesis method and an application. Background technique [0002] Among the various organic photochromic compound systems currently being studied, diarylene derivatives have become the most promising optical storage materials in the field of information storage due to their outstanding thermal irreversibility and good fatigue resistance. These factors have made people devote more enthusiasm and energy to design and synthesize new diarylene compounds with excellent properties. In addition, diarylene derivatives have promising application prospects in many fields (such as molecular switches) due to their good photophysical and photochemical properties. Fluorescent molecular switching and chemical sensing of diarylene has attracted the attention of the world. This new characteristic will further drive the development of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D409/14C09K11/06C09K9/02
CPCC07D409/14C09K9/02C09K11/06C09K2211/1092
Inventor 蒲守智刘刚魏沙沙崔士强
Owner JIANGXI SCI & TECH NORMAL UNIV
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