Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Rapid-response photoisomerization 4-perfluoroalkyl azobenzene allyl ether and preparation method thereof

A fluoroalkyl azophenyl propenyl ether, photoisomerization technology, applied in the field of azo photochromic materials, can solve the problem of slow light response speed, etc., and achieve the effect of rapid response and wide application fields

Inactive Publication Date: 2015-03-11
DONGHUA UNIV
View PDF5 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] What the present invention aims to solve is the problem that the photoresponse speed of existing azobenzene compounds with photochromic phenomenon is relatively slow

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Rapid-response photoisomerization 4-perfluoroalkyl azobenzene allyl ether and preparation method thereof
  • Rapid-response photoisomerization 4-perfluoroalkyl azobenzene allyl ether and preparation method thereof
  • Rapid-response photoisomerization 4-perfluoroalkyl azobenzene allyl ether and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1. Preparation of 4-perfluorooctyl azophenyl propenyl ether

[0033] (1) Add copper powder (0.9616g) to a three-necked bottle equipped with a reflux device to remove water and oxygen and fill with nitrogen for protection, and add p-iodoaniline (1.0952g) and perfluorooctyl iodide under the condition of magnetic stirring at 120°C Alkanes (3.0032g) in DMSO solution 15mL, react for 5-10 hours until the reaction is complete. After the reaction, filter to remove excess copper powder and cuprous iodide, wash the reaction solution with 50mL ether and 50mL aqueous solution, wash the ether layer three times with 50mL aqueous solution to remove DMSO and excess perfluorooctyl iodide, and decompress the washed ether layer It was spin-dried and purified by column chromatography to obtain perfluorooctylaniline (colorless solid, yield 81.5%).

[0034] (2) Add 1.5mL of 12M concentrated hydrochloric acid dropwise to 1.0224g of perfluorooctylaniline under ice bath conditions (0-5°C), dis...

Embodiment 2

[0039] 1. Preparation of 4-perfluorohexyl azophenyl propenyl ether

[0040] (1) Add copper powder (0.9704g) to a three-necked bottle equipped with a reflux device to remove water and oxygen and fill with nitrogen for protection, and add p-iodoaniline (1.0875g) under magnetic stirring conditions at 120°C, and perfluorohexyl iodide (2.4538g) in 15 mL of DMSO solution, react for 5-10 hours until the reaction is complete. After the reaction, filter to remove excess copper powder and cuprous iodide, wash the reaction solution with 50mL ether and 50mL aqueous solution, wash the ether layer three times with 50mL aqueous solution to remove DMSO and excess perfluorooctyl iodide, and decompress the washed ether layer It was spin-dried and purified by column chromatography to obtain perfluorohexylaniline (colorless solid, yield 84.27%).

[0041] (2) Add 1.5mL of 12M concentrated hydrochloric acid dropwise to perfluorohexylaniline (0.8226g) under ice bath conditions (0-5°C), dissolve und...

Embodiment 3

[0047] 1. Preparation of 4-perfluorobutyl azophenyl propenyl ether

[0048] (1) Add copper powder (0.9654g) to a three-necked bottle equipped with a reflux device to remove water and oxygen and fill with nitrogen for protection, and add p-iodoaniline (1.0936g) under magnetic stirring conditions at 120°C, and perfluorobutyl iodide Alkanes (1.9246g) in DMSO solution 15mL, react for 5-10 hours until the reaction is complete. After the reaction, filter to remove excess copper powder and cuprous iodide, wash the reaction solution with 50mL ether and 50mL aqueous solution, wash the ether layer three times with 50mL aqueous solution to remove DMSO and excess perfluorooctyl iodide, and decompress the washed ether layer Spin to dry and purify by column chromatography to obtain perfluorobutylaniline (colorless liquid, yield 86.52%).

[0049] (2) Add 1.5mL of 12M concentrated hydrochloric acid dropwise to perfluorobutylaniline (0.6248g) under ice bath conditions (0-5°C), dissolve under ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
boiling pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses rapid-response photoisomerization 4-perfluoroalkyl azobenzene allyl ether and a preparation method thereof. The general structural formula of 4-perfluoroalkyl azobenzene allyl ether is shown in the Specification. The preparation method includes the following steps: dissolving the starting compounds, 4-iodoaniline and fluorine-containing alkyl iodide, into a high boiling point solvent, and under the protection of nitrogen, heating, and catalyzing the solvent by copper powder to obtain fluoroalkyl aniline; after diazotizing fluoroalkyl aniline using hydrochloric acid / nitrite system at a temperature of 0-5 DEG C, enabling the diazotized solution to react with the phenol alkaline solution to obtain perfluoroalkyl azo phenol; under the protection of nitrogen, heating perfluoroalkyl azo phenol and 3-bromopropylene in an anhydrous and oxygen-free polar solvent under a weak base condition to obtain 4-fluoroalkyl azobenzene propenyl ether. The fluorine-containing azobenzene compound photoisomerization provided by the invention can response rapidly, has an active functional group propenyl, is capable of participating in addition reactions or polymerization reactions, and can be applied widely.

Description

technical field [0001] The invention relates to a method for synthesizing a photoisomerized azobenzenefluoroalkyl compound, which belongs to the field of azo photochromic materials. Background technique [0002] Azobenzene compounds can undergo cis-trans isomerization under the action of light or heat. When the cis-trans isomerization occurs, the geometric size and dipole moment of the molecule will also change accordingly, thereby changing the physical and chemical properties of the azo compound, and it has been widely used in the fields of optical data storage, optical molecular switches, optical sensors, etc. . [0003] Among them, the fluorine-terminated azobenzene compounds have broad potential application prospects in liquid crystals, optically adjustable wettability surfaces, and protein adsorption controllable surfaces. [0004] It has been reported that azobenzene compounds (Formula 1) containing trifluoromethyl end groups can be used to prepare photoresponsive su...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07C245/08
Inventor 高宇黄建宝黄焰根何创龙
Owner DONGHUA UNIV
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com