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A near-infrared ratiometric fluorescent probe for detecting hydrazine and its application

A ratiometric fluorescent probe and fluorescent probe technology, applied in the field of organic small molecule fluorescent probes, can solve the problems of short wavelength, inability to detect gaseous hydrazine, and inability to achieve cell imaging, achieving good fluorescence ratio response effect and broad application prospects Effect

Inactive Publication Date: 2017-03-01
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Applied patents [CN103923071A] and [CN104109126A] show fluorescent probes that specifically select hydrazine, but they all have shortcomings such as short wavelength, inability to detect gaseous hydrazine, and inability to realize cell imaging.

Method used

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  • A near-infrared ratiometric fluorescent probe for detecting hydrazine and its application
  • A near-infrared ratiometric fluorescent probe for detecting hydrazine and its application
  • A near-infrared ratiometric fluorescent probe for detecting hydrazine and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] 2-(2-hydroxyl-4-diethylaminobenzoyl) benzoic acid and 3-acetyl-7 diethylaminobenzoyl coumarin synthesized by a known method are reacted at temperature in concentrated sulfuric acid, and the reaction solution is cooled , add perchloric acid oxidation to obtain 4-(2'-methylcarboxyphenyl)-2-(7'-diethylaminocoumarin)-7-diethylaminobenzopyran perchlorate with red fluorescence salt. specifically is:

[0029] Add 2-(2-hydroxy-4-diethylaminobenzoyl)benzoic acid (3, 5.0 mmol), 3-acetyl-7 diethylamino coumarin (5.0 mmol) into 5 mL of concentrated sulfuric acid , heated to 90°C and controlled for 8 hours, cooled to room temperature, added 10g of ice, then added 1mL of 70% perchloric acid and stirred, a black solid was precipitated, filtered with suction, washed with water three times, and the crude product was recrystallized with ethanol to obtain a dark green solid which was 4 -(2'-methylcarboxyphenyl)-2-(7'-diethylaminocoumarin)-7-diethylaminobenzopyran perchlorate (BPCC), mel...

Embodiment 2

[0037] 10 equivalents of N 2 h 4 ,CH 3 CO 2 - ,Br - ,H 2 PO 4 - , HCO 3 2- ,HPO 4 2- , HSO 3 - ,I - ,NO 2 - ,NO 3 - , SO 3 2- , SO 4 2- , Ca 2+ ,Cu 2+ , Fe 3+ ,K + ,Mg 2+ , Na 2 S, Zn 2+ After 2 hours of action, the UV-visible spectrophotometry and fluorescence spectrophotometry tests were performed, showing that the probes were sensitive to N 2 h 4 There is good selectivity, adding N 2 h 4 The before and after comparison shows that the ultraviolet absorption wavelength and the fluorescence emission wavelength have a blue shift of 167 and 201nm, respectively, which has a very good ratio response. See figure 2 , 3, 4.

Embodiment 3

[0039] Fluorescence test in fetal bovine serum.

[0040] At 37°C, 100% fetal bovine serum was incubated with 5 μM probes and different concentrations of N 2 h 4 (0, 10, 50, 100, 500, 1000μM) were incubated together for 2h. Pure serum has basically no fluorescence in the two channels, the probe shows weak light in the blue channel, and strong fluorescence in the red channel. 2 h 4 As the concentration increases, the blue fluorescence gradually strengthens, and the red fluorescence gradually weakens, see Figure 5 .

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Abstract

The present invention discloses a near-infrared hydrazine ratio fluorescence probe, and the probe is dicoumarol-containing 4 - (2 '- carboxyl phenyl) - 2 - (7' - diethylamine coumarin) - 7 - diethylamino benzo pyran perchlorate with the chemical structural formula shown in formula (I). The probe can selectively effect with N2H4 to change from green to yellow, can be distinguished by the naked eye, fluorescence changes from red to blue-green, and fluorescence ratio response effect is very good, and can also be analyzed by UV absorption and fluorescence spectrometry. N2H4 ratio detecting can be achieved, intracellular ratio imaging can be achieved, and the content of the gaseous N2H4 can be quickly detected by the naked eye by use of a prepared silica gel plate. The probe is expected to play a role in industrial production and biological sciences, and has broad application prospects.

Description

technical field [0001] The invention relates to a near-infrared fluorescent probe, in particular to a near-infrared fluorescent probe for detecting hydrazine and an application thereof; it belongs to the field of organic small molecule fluorescent probes. Background technique [0002] The parent ring of coumarin is a benzopyrone structure, which itself has a large molar extinction coefficient and quantum yield. There are multiple sites that can be modified, and it can achieve near-infrared luminescence. It can be used in luminescent materials, chemical sensors and labels. biomolecules etc. In recent years, the use of ratiometric fluorescence effect to detect small molecule hydrazine has been continuously developed. [0003] Hydrazine is a very important active base and strong reducing agent. It can be used as a catalyst, emulsifier, pharmaceutical intermediate, textile dye, photographic chemical, etc. in the chemical field. At the same time, as a high-energy propellant, hy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64G01N21/78
CPCC07D311/16C09K11/06C09K2211/1007C09K2211/1088G01N21/6428G01N21/6447G01N21/6486G01N21/78
Inventor 赵宝祥苗俊英戴溪王朝阳
Owner SHANDONG UNIV
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