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

Substituent acetophenone group purpurine derivative of high-sensitivity color changing material and synthetic method thereof

A technology of acetophenone-based viologen and derivatives, which is applied in the direction of color-changing fluorescent materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of poor stability and low sensitivity of color change, and achieve less side reactions, sensitive response, suitable for The effect of mass production

Inactive Publication Date: 2015-08-26
SHANGHAI UNIV
View PDF3 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] One of the objectives of the present invention is to overcome the problems of low discoloration sensitivity and poor stability in the prior art, and provide a substituted acetophenone-based viologen derivative

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
  • Substituent acetophenone group purpurine derivative of high-sensitivity color changing material and synthetic method thereof
  • Substituent acetophenone group purpurine derivative of high-sensitivity color changing material and synthetic method thereof
  • Substituent acetophenone group purpurine derivative of high-sensitivity color changing material and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment one : Synthetic 3,4-dichloroacetophenone substituent viologen, adopt the following steps:

[0028] ① First, take 4,4'-bipyridine (1.56g, 10mmol) and α-chloro-3,4-dichloroacetophenone (5.58g, 25mmol) in a 50 mL single-necked round bottom flask, and use anhydrous DMF (20 mL) dissolved. The solution was refluxed at 120 oC for 24 hours, during which a light gray precipitate was formed.

[0029] ② After the reaction, cool to room temperature, centrifuge to get the precipitate, wash 3 times with anhydrous DMF, 4 times with high-purity water, and 4 times with acetone. The washing solution changes from brownish yellow to almost colorless. After the precipitate was centrifuged and dried in vacuum for 8 hours, the obtained product was 3.83 g (63.47%) of 3,4-dichloroacetophenone substituent viologen.

[0030] ③ The physical parameters of the compound: see Figure 1 to Figure 4 .

[0031] ④ Molecular formula: C 26 h 18 N 2 o 2 Cl 6

[0032] ⑤ Structural for...

Embodiment 2

[0041] Embodiment two : Synthesis of 3,4-dihydroxyacetophenone substituent viologen, adopt the following steps:

[0042] ① Weigh 4,4'-bipyridine (1.56g, 10mmol) and 4-chloroacetyl-1,2-catechol (4.66g, 25mmol) in a 50 mL single-necked round bottom flask, and use anhydrous DMF ( 20mL) dissolved. solution in N 2 Stir under protection, heat to 120 oC, and reflux for 24 hours, during which a yellow precipitate is formed.

[0043]② Cool to room temperature after the reaction, centrifuge to get the precipitate, wash it with anhydrous DMF and acetone for 3~5 times respectively, centrifuge and vacuum dry for 8 hours, the product obtained is 3,4-dihydroxyacetophenone substituent viologen 2.25g (64.5%).

[0044] ③ The physical parameters of the compound: see Figure 5 to Figure 8

[0045] ④ Molecular formula: C 26 h 22 o 6 N 2 Cl 2

[0046] ⑤ Structural formula:

[0047]

[0048] ⑥ Chinese name: 3,4-dihydroxyacetophenone instead of viologen

[0049] ⑦ English name: 3,...

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 relates to a substituent acetophenone group purpurine derivative and a synthetic method thereof. The structure of the derivative is described in the abstract of the specification, wherein R is H or other substituent group (an electron-withdrawing group is preferred), and X is halogen. 5*10-5 M above purpurine compound water solution is highly sensitive to Lewis base, the existence of organic base and inorganic base which are less than 1.0 ppm makes the purpurine compound water solution change into red color from achromatic color. Reversible color changing test paper specific to alkali steam can be prepared by coating the solvent thereof on a carrier (such as paper). The synthetic reaction raw material is cheap and easy to obtain, the side reaction is less, the solvent has low toxicity, the operation is very simple, the rate of production can reach 60-70%, and therefore, the substituent acetophenone group purpurine derivative is suitable for mass production.

Description

technical field [0001] The invention relates to a novel viologen derivative and a preparation method thereof, in particular to a substituted acetophenone-based viologen derivative and a synthesis method thereof. Background technique [0002] Viologens, the cationic salts of N,N'-disubstituted-4,4'bipyridines, were first discovered by Weidel and Russo in 1882. Its original structure, methyl viologen, was widely used as an agricultural herbicide in the 20th century, with obvious biological effects on green leafy plants. In the second half of the 20th century, it was discovered that viologens have electron-deficient properties and their characteristic two-step redox process. As an excellent electron acceptor, viologen compounds have dications (V 2+ ), cationic radicals (V ·+ ) and electrically neutral molecules (V 0 ) in three forms. And the conversion between the three often requires only a relatively small potential change to cause a color-changing reaction. Among them,...

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): C07D213/04C09K9/02
CPCC07D213/04C09K9/02C09K2211/1029
Inventor 施玮朱守荣邢菲菲
Owner SHANGHAI 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