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3,4-difluoroacetophenone substituted viologen compound and preparation method and application thereof

A technology for difluoroacetophenone and compound, which is applied in 3, can solve the problems of harsh conditions for viologen discoloration, the substance detection line needs to be improved, and the color development period of the compound is short, so as to achieve simple operation, high yield and easy purification. Effect

Inactive Publication Date: 2017-12-26
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although the discoloration advantage of viologen compounds is relatively obvious, since the discoloration substance is viologen free radicals, the conditions for viologen discoloration may be relatively harsh, and some of them must be in an oxygen-free state to have obvious effects. Instability, the color development cycle of this kind of compound is short, and the detection line for the substance needs to be improved

Method used

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  • 3,4-difluoroacetophenone substituted viologen compound and preparation method and application thereof
  • 3,4-difluoroacetophenone substituted viologen compound and preparation method and application thereof
  • 3,4-difluoroacetophenone substituted viologen compound and preparation method and application thereof

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Effect test

Embodiment 1

[0045] Embodiment one: the synthetic acetophenone substituent novel viologen adopts the following steps:

[0046] ① Weigh 4,4'-bipyridine (1.56g, 10mmol) and 4-chloroacetyl-1,2-difluorobenzene (4.66g, 25mmol) in a 50mL single-necked round-bottomed flask, and use anhydrous DMF (15mL) dissolve. The solution was refluxed at 120°C for 36 hours, during which a light yellow precipitate was formed. After the reaction was completed, cool to room temperature, centrifuge to obtain a precipitate, and then wash with anhydrous DMF and acetone for 3 to 5 times, until the washing liquid turns from brown to almost colorless, and the crude product is obtained.

[0047] ②At room temperature, add high-purity water to the crude product drop by drop until completely dissolved. After adding a large amount of acetone to the solution, a large amount of light white precipitates precipitated out. After the precipitate was centrifuged and dried in vacuum for 8 hours, the obtained product was 3.55 g (...

Embodiment 2

[0048] Embodiment 2: Alkali titration 3,4-difluoroacetophenone substituent novel viologen adopts the following steps:

[0049] First prepare 1×10 of 3,4-difluoroacetophenone substituent viologen -5 and 5×10 -3 Aqueous solution of M, then NaOH, phenethylamine, diethylamine, diisopropylamine, Na 2 CO 3 , piperazine, triethanolamine, triethylenetetramine and triethylamine were titrated with different equivalents, and the solution after titration was tested for ultraviolet-visible absorption spectrum. In the alkali titration process, the phenomenon is almost the same, with the increase of the amount of alkali, the solution changes from colorless to pink to red.

Embodiment 3

[0050] Embodiment 3: The following steps are used to make the temperature-sensitive test paper of the new viologen substituent of 3,4-difluoroacetophenone:

[0051] First prepare 1×10 of 3,4-difluoroacetophenone substituent viologen -2 ~1×10 -3 M aqueous solution, and then soak the clean test paper in the solution, take it out, put the test paper in the natural environment to dry, and obtain the viologen temperature and acid-base gas sensing test paper. The color of the test paper changes from white to purple as the temperature increases and the purple color deepens as the temperature increases. The test paper for NH 3 Gas is very sensitive, in case of NH 3 The color changed to blue-purple, and the discolored test paper was treated with HCl gas to become white. The test paper can be used for temperature and acid-base gas (such as NH 3 ) sensing is reversible.

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Abstract

The invention discloses a 3,4-difluoroacetophenone substituted viologen compound and a preparation method and an application thereof. A structural formula is shown as a specification, and the viologen is sensitive to an alkalescence substance. The temperature-sensing test paper produced by viologen is sensitive to change of the perception temperature, and can be reused. The viologen has good machinery grinding discoloration performance, and is conveniently used for pressure sensing. A compound aqueous solution can be used for alkali visualization detection, the color of the temperature-sensing test paper at the temperature of 18-80 DEG C is changed from colorless to light purple to dark purple, and the temperature-sensing test paper can be reused. After grinding for 1 min, the color of a sample is changed from white to purple.

Description

technical field [0001] The invention relates to an aroacetyl viologen compound and its preparation method and application. In particular, a 3,4-difluoroacetophenone substituted viologen compound and its preparation method and application. Background technique [0002] Since viologen compounds were reported by Weidel and Russo in 1882, people have conducted continuous research on these compounds. Among them, the most well-known is methylviologen-paraquat, which is a cationic salt of N,N'-dimethyl-4,4'-bipyridine with two positive charges, and was widely used in the 20th century. Used as a herbicide, it has a certain effect on the photosynthesis of green plants, but it is highly toxic to the human body and can cause fibrosis of human organs, so it has been banned. In 1932, Michaelis et al. found that the viologen compound could be reduced to two states, and the cationic free radical of viologen was purple, so the N,N'-dimethyl-4,4'-bipyridine cationic salt compound was Name...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/04C09K9/02G01K11/16G01L1/00G01L11/00G01N21/78
CPCG01K11/16G01L1/00G01L11/00G01N21/78C09K9/02C07D213/04C09K2211/1007C09K2211/1029
Inventor 胡美玲乔焕焕朱守荣邢菲菲
Owner SHANGHAI UNIV
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