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Arylsalicylaldehyde-diphenyl-azine hydrazine compound as well as preparation and application

A technology of aryl salicylaldehyde and diphenyl, which is applied in the field of analysis and detection materials, can solve problems such as difficult detection and fluorescence analysis, decrease in fluorescence quantum yield, high non-radiative transition ratio, etc., and achieve strong fluorescent probe characteristics , increase Stokes displacement, and enhance the effect of AIE performance

Active Publication Date: 2016-05-04
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, the rapid intramolecular free rotation effect in the conventional hydrazine structure (the lone pair of electrons is small in size, prone to cis-trans isomerization) and the high non-radiative transition ratio in the aggregated state lead to a decrease in its fluorescence quantum yield Seriously, it is difficult to apply to detection and fluorescence analysis under conventional water system conditions, such as the study of intracellular substructure, the monitoring of metal ions in water systems, etc.

Method used

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  • Arylsalicylaldehyde-diphenyl-azine hydrazine compound as well as preparation and application
  • Arylsalicylaldehyde-diphenyl-azine hydrazine compound as well as preparation and application
  • Arylsalicylaldehyde-diphenyl-azine hydrazine compound as well as preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] The synthesis of salicylaldehyde-diphenyl-azine hydrazine (DBAS), the synthetic route is shown in the following formula:

[0062]

[0063] The specific synthesis steps are: reflux reaction of 10g diphenylhydrazine and 5ml salicylaldehyde in 100ml ethanol solvent for 2 hours, cool to -10°C after the reaction is completed, filter at low temperature after a large amount of needle-packed solids are precipitated, and weigh the crude product with ethanol Crystallized twice to obtain pale colorless needle-packed crystals of salicylaldehyde-diphenyl-azinehydrazine (DBAS) with a purity of 99% and a yield of 90%. The product identification data are: 1 HNMR(400MHz,d-DMSO,ppm):11.28(s,1H,-OH),8.75(s,1H),7.64-7.62(m,2H),7.54-7.41(m,7H),7.28-7.24( m,3H), 6.29-6.26(m,1H), 5.95(d,1H). MALDI-TOF(m / z):[M+]calcd.C 20 h 14 N 2 O, 298.11; found, 298.11.

[0064] The optical properties of DBAS obtained in this example and its application in cell staining and metal ion sensing:

[0...

Embodiment 2

[0073] Take 1g of diphenylhydrazine crystals and equimolar 1-naphthyl salicylaldehyde in 50ml of ethanol and react at 60°C for 2h. After the reaction is completed, cool to obtain light yellow crystals. After filtering the solids, wash them with 75% aqueous ethanol. The obtained naphthyl salicylaldehyde-diphenyl-azine hydrazine (DBNAS) has a product purity of 99% and a yield of >95%. The product identification data is: MALDI-TOF(m / z):[M+]calcd.C 24 h 18 N 2 O, 350.41; found, 350.65. AnalCalc.forC 24 h 18 N 2 O: C, 82.26; H, 5.18; N, 7.99; O, 4.57. Found: C, 82.24; H, 5.16; N, 7.94; O, 4.60. The product structure is shown in the following formula:

[0074]

[0075] The optical properties of DBNAS obtained in this example and its application in intracellular staining:

[0076] (a) Basic optical properties of DBNAS:

[0077] The fluorescence spectra of DBNAS in different polar solvents are as follows: Figure 8 shown by Figure 8It can be seen that with the change of ...

Embodiment 3

[0081] The synthesis of DBAS nitrogen ethyl derivatives, concrete synthetic steps are as follows:

[0082] Take 1g of diphenylhydrazine (or N,N-diethylaminodiphenylhydrazine) and equimolar N,N-diethylaminosalicylaldehyde (or salicylaldehyde) in 30ml of ethanol at 60°C Reaction 4h, cooling after completion of the reaction, extraction and liquid separation, column chromatography to obtain the following corresponding products:

[0083]

[0084] N-DBAS: yellow solid, 87% yield. The product identification data is: MALDI-TOF(m / z):[M+]calcd.C 24 h 25 N 3 O: 371.47; found, 371.88; AnalCalc.forC 24 h 25 N 3 O: C, 77.60; H, 6.78; N, 11.31; O, 4.31. Found, C, 77.55; H, 6.74; N, 11.30; O, 4.32;

[0085] DBAS-2N: pale yellow solid, yield 85%. The product identification data is: MALDI-TOF(m / z):[M+]calcd.C 28 h 34 N 4 O: 442.27; found, 442.30; AnalCalc.forC 28 h 34 N 4 O: C, 75.98; H, 7.74; N, 12.66; O, 3.61. Found, C, 75.78; H, 7.69; N, 12.34; O, 3.71;

[0086] N-DBAS-2N: ...

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Abstract

The invention belongs to the technical field of analysis and detection materials, and discloses an arylsalicylaldehyde-diphenyl-azine hydrazine compound as well as preparation and application. The compound has a structural general formula of formula (1) shown in the description, wherein Ar represents an aryl group or a derivative structure thereof, and substituent groups R1 to R10 are respectively selected from hydrogen, alkyl, alkoxy, aryl group and relative derivative structures thereof. The preparation method of the compound comprises the following steps: heating diphenyl hydrazine derivative and arylsalicylaldehyde to be 30 to 90 DEG C in a solvent for 6 to 12 hours' reaction, and separating and purifying reaction products, so as to obtain the arylsalicylaldehyde-diphenyl-azine hydrazine compound. The compound provided by the invention shows strong characters of a fluorescence probe, and also shows stronger selective recognition capability to substructures and metal ions in a cell, thereby achieving great high development value.

Description

technical field [0001] The invention belongs to the technical field of analysis and detection materials, and in particular relates to an aryl salicylaldehyde-diphenyl-azine hydrazine compound and its preparation and application. Background technique [0002] With the rapid development of the national economy and the continuous improvement of people's living standards, real-time monitoring of personal health, disease prevention and treatment have gradually become people's livelihood issues that people pay more attention to. Compared with the delay of traditional in vitro chemical testing and the harmfulness of online radiation detection, fluorescence online imaging technology has gradually entered people's field of vision with its advantages of high efficiency, greenness and strong real-time performance, and has been widely used in cellular immunology, microbiology, etc. Science, molecular biology, genetics, neurobiology, pathology, oncology, clinical laboratory science, medi...

Claims

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Application Information

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IPC IPC(8): C07C251/88C07C249/16C07C253/30C07C255/50C07D333/32C07D209/88C07D215/20C07D209/36C07D311/30C07D239/36C07D209/86C07D213/04C07D295/088C09K11/06G01N21/64
CPCC07C249/16C07C251/88C07C253/30C07C255/50C07D209/36C07D209/86C07D209/88C07D213/04C07D215/20C07D239/36C07D295/088C07D311/30C07D333/32C09K11/06C09K2211/1007C09K2211/1011C09K2211/1014C09K2211/1029C09K2211/1044C09K2211/1088C09K2211/1092G01N21/64
Inventor 唐本忠王志明赵祖金秦安军赵恩贵归晨王京
Owner SOUTH CHINA UNIV OF TECH
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