Preparation method and application of a solid-state acid-base stimuli-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

Active Publication Date: 2022-02-22
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 a solid-state acid-base stimuli-responsive near-infrared fluorescent compound
  • Preparation method and application of a solid-state acid-base stimuli-responsive near-infrared fluorescent compound
  • Preparation method and application of a solid-state acid-base stimuli-responsive near-infrared fluorescent compound

Examples

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 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 suction filtered to obtain compound 3 as a purple crystal with a yield of 88.2%;

[0045] 1 HNMR (400Hz, CD...

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Abstract

The invention provides a solid-state acid-base stimulus-responsive near-infrared fluorescent compound 1, the molecular chemical formula of which is shown in formula (I): the invention discloses a solid-state acid-base stimulus-response The preparation method and application of the near-infrared fluorescent compound. Among them, triphenylamine and cyanopyridine are common fluorescent compound units, but the unique chemical structure makes this compound have the advantages of aggregation-induced luminescence characteristics and high solid-state luminescence, and can respond to acid-base stimuli. Under the light, it can be observed that the fluorescence changes from the deep red-near-infrared region at 652nm to the fluorescence emission at 789nm near-infrared I region, with a shift of up to 137nm. In daylight, it can be seen that it changes from red to blue-black. Therefore, the present invention provides a solid-state acid-base stimulus-responsive near-infrared fluorescent material, which has broad application prospects in the fields of stimulus-responsive switch molecular devices, sensing, and anti-counterfeiting.

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 Patents(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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