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Buzane-based azine structure compound based on meta-position linkage and preparation method and application thereof

A compound, hydrazine technology, applied in the field of analysis and detection, can solve the problems of inability to realize the application of red fluorescent probes, and achieve the effect of excellent aggregation-induced luminescence characteristics

Active Publication Date: 2017-03-15
HKUST SHENZHEN RES INST
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The object of the present invention is to provide a dihydrazine azine structure compound based on a meta-linkage and its preparation method and application, which solves the problem that the dihydrazine azine structure compound in the prior art is mainly yellow fluorescent and cannot be realized as a red color. Problems with Fluorescent Probe Applications

Method used

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  • Buzane-based azine structure compound based on meta-position linkage and preparation method and application thereof
  • Buzane-based azine structure compound based on meta-position linkage and preparation method and application thereof
  • Buzane-based azine structure compound based on meta-position linkage and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0066] Embodiment 1: the synthesis of cyano salicylaldehyde azine (CN-SAA)

[0067]

[0068] Reflux 0.5g of p-cyanobenzene salicylaldehyde and hydrazine hydrate under 25ml of ethanol for 4h (add acetic acid as a catalyst), remove the ethanol under reduced pressure after cooling, extract, and separate the organic phase with a column after drying to obtain 0.52g of a light yellow solid. It is the CN-SAA structure. MALDI-TOF (m / z): [M+]calcd.C 28 h 18 N 4 o 2 , 442.143; found, 443.15.Anal Calc.for C 28 h 18 N 4 o 2 : C, 76.01; H, 4.10; N, 12.66; O, 7.23. Found: C, 75.78; H, 4.04; N, 12.33; O, 7.05.

Embodiment 2

[0069] Example 2: Study on the ESIPT and AIE properties of CN-SAA

[0070] Such as Figure 1A It is the fluorescence spectrum of CN-SAA under different polarities. With the change of polarity, the ratio of alcohol emission (near 426nm) and ketone emission (near 579nm) of CN-SAA changes obviously, which is a typical ESIPT emission . For ESIPT molecules, the aggregation state is mostly ketone emission, so we detected the aggregation luminescence phenomenon at this place. Such as Figure 1B As shown, a certain proportion of water was continuously added to the THF solvent of CN-SAA (dissolved single molecular state), and CN-SAA slowly aggregated into nanoparticles due to solubility problems, and the fluorescence intensity of the alcohol form gradually decreased, and the intensity of the ketone form increased. The proportion of those increased with the increase of water content, indicating that CN-SAA has AIE properties. The ESIPT and AIE properties suggest that CN-SAA has the p...

Embodiment 3

[0071] Example 3: Research on the responsiveness of CN-SAA to metal ions

[0072] Such as Figure 2A with 2B Shown are the experimental results of the selection of different metal ions by CN-SAA in aqueous solution. Through comparison, it is found that the fluorescent probe has a specific response to copper ions, and its fluorescence intensity around 579nm is significantly reduced, and there is a certain linear relationship. ; Through the interference experiment results, it can be seen that the detection of copper ions has little influence on the presence of other ions.

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Abstract

The invention relates to a buzane-based azine structure compound based on meta-position linkage and a preparation method and application thereof. The compound can serve as a red probe, has excellent aggregation-induced emission characteristics, and can be used for selectively and quantitatively recognizing metal ions under the water system condition. Effective red shift of solid fluorescence and adjustment of the ESIPT type molecular alcohol ketone proportion, ion selectivity and the detection limit are achieved through the capacity change of pushing-drawing substitutes with substituent groups, and the red fluorescent probe has important application and significance in the fields of chemical sensing, bioanalysis, ion detection and the like.

Description

technical field [0001] The invention relates to the technical field of analysis and detection, more specifically, to a dihydrazinyl azine structure compound based on a meta-linkage and a preparation method and application thereof. Background technique [0002] There are many kinds of alkali metals, alkaline earth metals, transition metals and heavy metal elements in nature, which play a very important role in the environment, biology, medicine and chemical sciences, and play a huge role. Beneficial metal ions play an important role in the life system, and the lack of them will affect normal physiological activities, and organisms need to take in an appropriate amount; while harmful metal ions are highly toxic and become potential carcinogenic and teratogenic factors, which are harmful to biological cells, The toxicity of tissues is very high, which can cause abnormalities in enzymes related to metabolism and biological protein synthesis. Therefore, rapid, simple, and accura...

Claims

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Application Information

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IPC IPC(8): C07C253/30C07C255/66C07C249/16C07C251/88C07D295/088C07D295/135C07D209/88C07D209/86C09K11/06G01N21/64
CPCC07C241/02C07C243/18C07C249/16C07C251/88C07C253/30C07C255/50C09K11/06G01N21/64
Inventor 唐本忠王志明赵祖金秦安军王京李小东
Owner HKUST SHENZHEN RES INST
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