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

A kind of photochromic compound and its preparation method and application

A photochromic and compound technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve problems such as reducing the effect of photochromic fluorescent switching, and achieve high yield, easy industrialization, and fewer synthesis steps. Effect

Active Publication Date: 2019-07-19
EAST CHINA UNIV OF SCI & TECH +1
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, most photochromic groups, such as spiropyran, dithiopheneethylene, stilbene, and azobenzene, basically have maximum absorption wavelengths in the ultraviolet region, while the maximum absorption wavelengths of fluorophores are basically also in the ultraviolet region. The emission is also around 400-500nm, and the overlapping region of the wavelengths of the two groups will reduce the effect on the photochromic fluorescent switch

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
  • A kind of photochromic compound and its preparation method and application
  • A kind of photochromic compound and its preparation method and application
  • A kind of photochromic compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The synthesis of embodiment 1 compound A1

[0060] synthetic route

[0061]

[0062] (a): Synthesis of compound 2 (pinacol 9-anthracene borate)

[0063] Take 9-bromoanthracene (1.7g, 6.6mmol), and diboronic acid pinacol ester (2g, 7.9mmol) were dissolved in 1,4-dioxane (20mL), and anhydrous potassium acetate (1.9g, 19.8 mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.6g, 0.7mmol), were added to the above system, heated to reflux at 100°C for 2h, TLC (thin layer chromatography ) Follow up and monitor the reaction until complete. Suction filtration, rotary evaporation to remove 1,4-dioxane, washing with saturated brine, extraction with dichloromethane three times, the combined organic phases were dried with anhydrous sodium sulfate, spin-dried, and separated by column chromatography (eluent was petroleum Ether: ethyl acetate = 100:1), to obtain a light yellow powder, that is, compound 2 (1.8 g, yield 90%).

[0064] (b): Synthesis of compound...

Embodiment 2

[0077] The synthesis of embodiment 2 compound A2

[0078] synthetic route

[0079]

[0080] (a): Synthesis of compound 7 (N-n-butyl-1,8-naphthoimide boronic acid pinacol ester)

[0081] Take 4-bromo-N-ethyl-1,8-naphthalimide (2.2g, 6.6mmol), diboronic acid pinacol ester (2g, 7.9mmol) was dissolved in 1,4-dioxane (20mL ), anhydrous potassium acetate (1.9g, 19.8mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (0.6g, 0.7mmol) were added to the above system , heated to reflux at 100° C. for 2 h, followed by TLC (thin layer chromatography) to track and monitor the reaction until it was complete. Suction filtration, rotary evaporation to remove 1,4-dioxane, washing with saturated brine, extraction with dichloromethane three times, the combined organic phases were dried with anhydrous sodium sulfate, spin-dried, and separated by column chromatography (eluent was petroleum Ether: ethyl acetate = 100:1), to obtain a light yellow powder, that is, compound 7 (2....

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

No PUM Login to View More

Abstract

The invention discloses a photochromic compound. The structure of the photochromic compound is represented by a formula A (shown in the description), wherein R represents a fluorescence group and represents substituted or unsubstituted naphthalene, anthracene, xanthenes, pyrene 1,8-naphthalimide, coumarin or pyran nitrile, and a substituent group on R is C1-C4 alkyl, halogen, hydroxide radical, C1-C4 alkoxy or C1-C4 alkyl amino; X represents oxygen, and Y represents C(CH3)2; or X represents N(CH3), and Y represents C(O). The invention further discloses an isomer of the photochromic compound, a mixture of the photochromic compound and the isomer and a preparation method and an application of the photochromic compound. The maximum absorption wavelength of a color-changing group of the photochromic compound is in a visible light region, but the maximum absorption wavelength of the fluorescence group is in an ultraviolet region and a near visible light region, so that the overlapping of the maximum absorption wavelengths of the two groups is effectively avoided. The photochromic compound has remarkable and special absorption and emitting properties in the ultraviolet region and the visible light region and can be used for producing photochromic fluorescence switches and molecular logic gates.

Description

technical field [0001] The invention belongs to the technical field of photochromic materials, in particular to a photochromic compound and its preparation method and application. Background technique [0002] The discoloration of photochromic compounds is basically caused by photoisomerization, bond breaking, or redox and dimerization of the compound. Among them, the triene compounds represented by Donor-Acceptor Stenhouse Adducts (DASA) are a class of excellent photochromic compounds, especially in the range of 450-750nm, 4∏ electrocyclization can occur, making it from colored to It becomes colorless, and can be changed from colorless to colored by heating or avoiding light in a variety of organic solvents (Hemmer J R, Poelma S O, Treat N, et al. Tunable Visible and Near Infrared Photoswitches. J. Am. Chem. Soc ., 2016, 138:13960-13966.). DASA-like photochromic materials have the advantages of being sensitive to visible light, high sensitivity, fast reaction speed, and f...

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 Patents(China)
IPC IPC(8): C07D403/06C07D405/14C09K11/06C09K9/02C09B57/06C09B23/16
CPCC07D403/06C07D405/14C09B23/16C09B57/06C09K9/02C09K11/06C09K2211/1029C09K2211/1044C09K2211/1088
Inventor 曲大辉杨舜叶序豪甘家安田禾
Owner EAST CHINA UNIV OF SCI & TECH
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