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Naphthyl acetyl viologen compound as well as compounding method and application thereof

A technology of naphthalene acetyl viologen and compounds, which is applied in chemical instruments and methods, analysis through chemical reaction of materials, organic chemistry, etc., can solve the instability of viologen free radicals and achieve excellent cationic free radical stability Excellent color performance, high productivity, and easy operation

Inactive Publication Date: 2017-12-01
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the discoloration advantage of viologen compounds is obvious, due to the instability of viologen free radicals, its application in detection is still under study

Method used

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  • Naphthyl acetyl viologen compound as well as compounding method and application thereof
  • Naphthyl acetyl viologen compound as well as compounding method and application thereof
  • Naphthyl acetyl viologen compound as well as compounding method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment one: Synthetic naphthyl acetyl substituent novel viologen adopts the following steps

[0035] ①Weigh 4,4'-bipyridine (1.56g, 10mmol) and 2-bromonaphthyl ethyl ketone (6.87g, 25mmol) into a 50mL single-necked round bottom flask, and dissolve it with anhydrous DMF (15mL). 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.

[0036] 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 yellow precipitates precipitated out. The precipitate was centrifuged and vacuum-dried for 8 hours to obtain 4.81 g (68.1%) of the naphthylacetyl s...

Embodiment 2

[0037] Embodiment two: the steps of viologen grinding sample:

[0038] Take an appropriate amount (≈4 mg) of viologen as a naphthalene acetyl substituent and place it in a clean agate mortar. After grinding the sample for ~10 minutes, the discoloration of the sample is basically complete.

[0039] Uses of the compounds of the invention.

[0040] 1. Through the UV-visible spectroscopic titration of NaOH and organic amines on the aqueous solution of naphthalene acetyl viologen, it is found that it has a very low detection limit for different alkalis and organic amines. This detection limit is used to detect low-concentration harmful organic amines Provides a good guarantee;

[0041] 2. The color reaction of naphthalene acetyl viologen compound in different solvents can be used as solvent color material;

[0042] 3. Through the research on the discoloration of naphthyl acetyl viologen compound after grinding, it can be used as a pressure sensor.

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Abstract

The invention discloses a novel naphthyl acetyl substituent viologen compound. A structure formula of the novel naphthyl acetyl substituent viologen compound is shown in the description. An enol viologen free radical with a larger conjugated system can be formed by viologen, the discoloring performance is excellent, and the viologen free radical is good in stability; the viologen is sensitive to alkaline matters, for example, the ultraviolet detection limit to organic amine is up to 10<-1>ppm. The viologen has obvious solvent developing effects in different solvents; the viologen has very good mechanical grinding and discoloring properties, and can be conveniently used for pressure sensing. In different solvents, the viologen compound has obvious developing effects; after the viologen compound is ground for 10 minutes, the color of a sample is changed from faint yellow to green.

Description

technical field [0001] The invention relates to a naphthyl acetyl viologen compound and its synthesis method and application. Background technique [0002] The viologen compound was first reported in 1882 and became the main agricultural herbicide-paraquat. This compound has two positive charges of N,N'-dimethyl-4,4'-bipyridine cationic salt and has been banned in many fields due to its high toxicity. However, as an organic color-changing material, it has many ways such as high color contrast, thermochromism, electrochromism, etc., which makes it attract the attention of many people. [0003] Due to the existence of two-step reversible redox reactions in viologen compounds, colored viologen cations can be freely produced during the process, so viologen compounds exhibit rich properties under the action of external physical and chemical stimuli, and are used in the fields of sensing and display. It has great application prospects. As an organic color-changing material, vio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/22C09K9/02G01N33/00G01N21/78G01L1/00
Inventor 程正敏胡美玲朱守荣邢菲菲
Owner SHANGHAI UNIV
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