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Preparation method and application of solid acid-base stimulus-responsive near-infrared fluorescent compound

A fluorescent compound and stimuli-responsive technology, applied in the field of preparation of near-infrared fluorescent compounds, can solve the problems of small fluorescence shift and low quantum efficiency of solid-state fluorescence, and achieve the effect of broad application prospects

Active Publication Date: 2019-11-22
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, this type of material has the disadvantages of low quantum efficiency of solid-state fluorescence, the luminous range is mostly in the visible light region, and the fluorescence shift after response is small.

Method used

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  • Preparation method and application of solid acid-base stimulus-responsive near-infrared fluorescent compound
  • Preparation method and application of solid acid-base stimulus-responsive near-infrared fluorescent compound
  • Preparation method and application of solid acid-base stimulus-responsive near-infrared fluorescent compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The synthetic method of above-mentioned compound 1, comprises the following steps:

[0024] Compound 1, the molecular formula is C 46 h 32 N 6 , emit red fluorescence under the irradiation of a 365nm ultraviolet lamp, and the molecular chemical formula of compound 1 is as shown in formula (I):

[0025]

[0026] Its preparation method, the steps are as follows:

[0027] 1) In a 250mL round bottom flask, mix 1g (2.13mmol) of 2,5-diphenylamine-1,4-dicarboxybenzene, 504.28mg (4.26mmol) of 3-pyridineacetonitrile and 37.804mL of absolute ethanol mixed to obtain a mixed solution;

[0028] 2) Dissolve 1.32g (33.08mmol) of sodium hydroxide in 37.8mL of absolute ethanol to obtain a sodium hydroxide-ethanol solution;

[0029] 3) Using a constant pressure dropping funnel, add sodium hydroxide-ethanol solution dropwise to the mixed solution under nitrogen protection, stir and react at room temperature for 1 hour, filter after cooling to room temperature, wash the obtained so...

Embodiment 2

[0033] The molecular chemical formula of compound 2 is shown in formula (II): the synthetic method comprises the following steps:

[0034]

[0035] 1) In a 250mL round bottom flask, mix 1g (2.13mmol) of 2,5-diphenylamine-1,4-dicarboxybenzene, 504.28mg (4.26mmol) of 2-pyridineacetonitrile and 37.804mL of absolute ethanol mixed to obtain a mixed solution;

[0036] 2) Dissolve 1.32g (33.08mmol) of sodium hydroxide in 37.8mL of absolute ethanol to obtain a sodium hydroxide-ethanol solution;

[0037] 3) Using a constant pressure dropping funnel, add sodium hydroxide-ethanol solution dropwise to the mixed solution under nitrogen protection, stir and react at room temperature for 1 hour, filter after cooling to room temperature, wash the obtained solid with water and ethanol alternately three times, After drying, it was recrystallized with dichloromethane and ethanol, and filtered to obtain orange-red crystal compound 2, with a yield of 78.2%;

[0038] 1 HNMR (400Hz, CDCl 3 , ...

Embodiment 3

[0040] The molecular chemical formula of compound 3 is shown in formula (III): the synthetic method comprises the following steps:

[0041]

[0042] 1) In a 250mL round bottom flask, mix 1g (2.13mmol) of 2,5-diphenylamine-1,4-dicarboxybenzene, 504.28mg (4.26mmol) of 4-pyridineacetonitrile and 37.804mL of absolute ethanol mixed to obtain a mixed solution;

[0043] 2) Dissolve 1.32g (33.08mmol) of sodium hydroxide in 37.8mL of absolute ethanol to obtain a sodium hydroxide-ethanol solution;

[0044]3) Using a constant pressure dropping funnel, add sodium hydroxide-ethanol solution dropwise to the mixed solution under the protection of nitrogen, stir and react at room temperature for 1 hour, cool to room temperature and filter, and wash the obtained solid with water and ethanol alternately three times, After drying, it was recrystallized with dichloromethane and ethanol, and suction filtered to obtain compound 3 as a purple crystal with a yield of 88.2%;

[0045] 1 HNMR (400...

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Abstract

The invention provides a solid acid-base stimuli-responsive near-infrared fluorescent compound 1. The molecular chemical formula of the solid acid-base stimuli-responsive near-infrared fluorescent compound 1 is shown as a formula (I). The invention discloses a preparation method and application of the solid acid-base stimuli-responsive near-infrared fluorescent compound containing a triphenylamineand cyanopyridine system. The triphenylamine and the cyanopyridine are common fluorescent compound units; however, due to the unique chemical structure, the compound has the advantages of aggregation-induced emission property and high solid-state luminescence; therefore, the fluorescent probe has the advantages that the fluorescent probe is high in sensitivity and high in sensitivity, and can respond to acid-base stimulation. In the invention, fluorescence of the fluorescent probe can be observed to be converted from the 652 nm dark red-near infrared region luminescence into the 789 nm near infrared I region fluorescence emission under a 365 nm ultraviolet lamp, wherein the shift reaches up to 137 nm. Under the sunlight, the color is changed from red to blue black. The invention providesthe solid acid-base stimulus-responsive near-infrared fluorescent material, wherein the material has a wide application prospect in the fields of stimulus-responsive switch molecular devices, sensing,counterfeiting prevention and the like.

Description

technical field [0001] The invention relates to the field of organic optical functional materials, in particular to a preparation method and application of a solid-state acid-base stimulus-responsive near-infrared fluorescent compound containing a triphenylamine and cyanopyridine system. Background technique [0002] Stimuli-responsive luminescent materials are a class of "smart" materials that change their absorption and emission spectra under external environmental stimuli (such as light, heat, pH, ions, pressure, small organic molecules, water, etc.) . In recent years, stimuli-responsive luminescent materials have received more and more support because of their unique properties of tunable fluorescence emission. Fields such as imaging have also been widely used, and thus have received more and more attention from researchers. Among them, the acid-base response refers to the phenomenon that the ultraviolet-visible absorption and fluorescence emission spectra of organic f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/57C09K11/06
CPCC07D213/57C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029
Inventor 吕宏光李阳阳赵晓伟
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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