Fluorescent viologen derivative, application and preparation method thereof

A derivative and fluorescence technology, used in chemical instruments and methods, fluorescence/phosphorescence, color-changing fluorescent materials, etc., can solve the problems of poor stability of viologen cation free radicals, low fluorescence quantum yield, limited application and development, etc. Achieve the effect of good pH sensing, excellent fluorescence performance, and good application value

Inactive Publication Date: 2018-08-07
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Due to the poor stability of viologen cation free radicals, unsustainable color development, and harsh use conditions, etc.
Therefore, the discoloration process of most viologens can only occur in a non-aqueous solution and an oxygen-free environment, which greatly limits its application and development in wider fields.
At the same

Method used

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  • Fluorescent viologen derivative, application and preparation method thereof
  • Fluorescent viologen derivative, application and preparation method thereof
  • Fluorescent viologen derivative, application and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0075] In this example, see figure 1 and figure 2 , a preparation method of fluorescent viologen derivatives, comprising the steps of:

[0076] Weigh 2mmol (0.364g) of 1,2-bis(4-pyridine)ethylene (bpe) and 5mmol (0.773g) of 2-chloroacetophenone in a single-necked flask, add 6ml of anhydrous DMF to fully dissolve, and then The above mixture solution was refluxed at 120° C. for 12 h. During the reaction process, a light yellow precipitate was formed. After the reaction was completed, it was cooled to room temperature, and the mixture was centrifuged. The precipitate was washed with anhydrous DMF and acetone for 3 to 5 times, and the supernatant after centrifugation changed from brown to colorless. Vacuum After drying at 80° C. for 8 hours, 0.689 g of light yellow powder was collected to obtain vinyl viologen. The yield of fluorescent viologen derivative Vio1 calculated based on 1,2-bis(4-pyridyl)ethylene was 70.2%.

[0077] Experimental test analysis:

[0078] The fluoresce...

Embodiment 2

[0086] This embodiment is basically the same as Embodiment 1, especially in that:

[0087] In this example, see figure 1 and figure 2 , a preparation method of fluorescent viologen derivatives, comprising the steps of:

[0088] Weigh 2mmol (0.364g) of 1,2-bis(4-pyridine)ethylene (bpe) and 5mmol (0.773g) of 2-chloroacetophenone in a single-necked flask, add 6ml of anhydrous DMF to fully dissolve, and then The above mixture solution was refluxed at 120° C. for 12 h. During the reaction process, a light yellow precipitate was formed. After the reaction was completed, it was cooled to room temperature, and the mixture was centrifuged. The precipitate was washed with anhydrous DMF and acetone for 3 to 5 times, and the supernatant after centrifugation changed from brown to colorless. Vacuum After drying at 80° C. for 8 hours, 0.689 g of light yellow powder was collected to obtain vinyl viologen. The yield of fluorescent viologen derivative Vio2 calculated based on 1,2-bis(4-pyri...

Embodiment 3

[0098] This embodiment is basically the same as the previous embodiment, and the special features are:

[0099] In this example, see figure 1 and figure 2 , a preparation method of fluorescent viologen derivatives, comprising the steps of:

[0100] Weigh 2mmol / L (0.364g) of 1,2-bis(4-pyridine)ethylene (bpe) and 5mmol / L (0.933g) of 3,4-dihydroxy-2'-chloroacetophenone in a single-necked flask 10ml of anhydrous DMF was added to fully dissolve, and then the above mixture solution was refluxed at 120°C for 24h. During the reaction process, a yellow precipitate was formed. After the reaction was completed, cool to room temperature, centrifuge the mixture, and wash the precipitate with anhydrous DMF and acetone for 3 to 5 times, until the supernatant after centrifugation changed from brown to colorless, vacuum 80 After drying at °C for 8 hours, 0.759 g of reddish-brown powder was collected to obtain vinyl viologen. The yield of fluorescent viologen derivative Vio3 calculated base...

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Abstract

The invention discloses fluorescent viologen derivatives, application and a preparation method thereof. A series of novel viologen derivatives with fast and visual solvent recognition and fast and sensitive color-change detection for the pH value at the alkaline range, the temperature and alkaline gases such as NH3 are prepared by utilizing a solvothermal method. Simultaneously, the series of fluorescent viologen derivatives are simple in synthesis method, high in yield, low in cost and strong in fluorescence. A viologen electrochromic device is good in color-change property and cyclic stability, low in color-change voltage, fast in color change and convenient in assembly. The fluorescent viologen derivatives can display the distinguished colors and the fluorescence emitting change in different organic solvents, so that the effect of detecting and distinguishing the organic solvents is achieved; after the novel viologen is used for preparing into test paper for detection, the detectioncapability in a solution state is retained, and the test paper can display different color changes so as to achieve the effect of sensing detection and recognition. The test of the viologen electrochromic device shows that the fluorescent viologen derivatives have good potential application value in the fields of electrochromic glass and displays and the like.

Description

technical field [0001] The invention relates to a fluorescent material, a color-changing material and its application and preparation method, in particular to a vinyl viologen substance or naphthaleneacetyl viologen substance and its application and preparation method, which are applied in the fields of chemical industry and material technology. It is especially applied in the technical fields of color-developing materials, colorimetric sensors and electrochromic devices. Background technique [0002] Due to its simplicity and sensitivity, visual colorimetric sensors have broad application prospects in the fields of environmental control, safety, and industrial plants. Viologen, an N,N disubstituted-4,4′-bipyridine cation salt, was first widely used as a herbicide. Due to its special electron-deficiency, it can undergo reversible redox reactions under different external light, heat, pressure, electricity and other environmental controls, and at the same time show obvious co...

Claims

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Application Information

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IPC IPC(8): C07D213/50C09K11/06C09K9/02G01N21/64G01N21/78
CPCC07D213/50C09K9/02C09K11/06C09K2211/1007C09K2211/1029G01N21/6428G01N21/78G01N2021/6439
Inventor 柏跃玲殷秀平李思锐胡勇进朱守荣
Owner SHANGHAI UNIV
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