A camphor-based fluorescent probe for detecting hydrazine and its preparation method

A fluorescent probe and camphor-based technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of long response time, poor water solubility, low sensitivity, etc., and achieve good practical value

Inactive Publication Date: 2021-05-18
NANJING FORESTRY UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the reported fluorescent probes still have defects such as long response time, low sensitivity, and poor water solubility.

Method used

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  • A camphor-based fluorescent probe for detecting hydrazine and its preparation method
  • A camphor-based fluorescent probe for detecting hydrazine and its preparation method
  • A camphor-based fluorescent probe for detecting hydrazine and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The preparation of camphor-based fluorescent probe, reaction formula is as follows:

[0033]

[0034] Specific steps are as follows:

[0035] 1) Preparation of 3-(4'-dimethylaminobenzylidene)-1,7,7-trimethylbicyclo[2.1.1]heptan-2-one:

[0036] Put 6mmol camphor, 6.5mmol p-dimethylaminobenzaldehyde, 12mmol sodium ethoxide and 30mL ethanol in a three-necked flask equipped with a stirrer, a thermometer and a reflux condenser in sequence, and heat it to reflux at 80-90°C to react for 5 hours to The conversion rate of camphor is more than 95% (GC tracking detection). The reaction solution was distilled to recover ethanol, then 25 mL of ethyl acetate was added, and washed with saturated brine until neutral. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated to recover the solvent to obtain 3-(4'-dimethylaminobenzylidene)-1,7,7-trimethylbicyclo[2.1.1]hept-2 - crude ketones. The crude 3-(4′-dimethylaminobenzylidene)-1,7,7-trimethylbicyc...

Embodiment 2

[0040] Compound 4-(4′-dimethylaminophenyl)-8,9,9-trimethyl-5,6,7,8-tetrahydro-5,8-endomethylene in different concentrations of hydrazine solutions The Ultraviolet Spectrum Properties of Quinazolin-2-amine

[0041] 4-(4'-dimethylaminophenyl)-8,9,9-trimethyl-5,6,7,8-tetrahydro-5,8-methanoquinazole obtained in Example 1 Phenyl-2-amine was formulated as 1 x 10 -5 M of PBS buffer solution (10mM, pH=7.4, 10% (v / v) ethanol), hydrazine is dissolved in the PBS buffer solution and is made into concentration and is 0,5,10,15,20,25,30,35, 40, 45, 50 μM solutions. Measured different concentrations of hydrazine to 4-(4'-dimethylaminophenyl)-8,9,9-trimethyl-5,6,7,8-tetrahydro-5,8-methanoquinone The ultraviolet absorption spectrum of oxazolin-2-amine, such as figure 1 shown. The results showed that the ultraviolet absorption of the compound at 400nm decreased obviously, while the absorption around 343nm increased obviously, which indicated that the compound could react with hydrazine.

Embodiment 3

[0043] Compound 4-(4′-dimethylaminophenyl)-8,9,9-trimethyl-5,6,7,8-tetrahydro-5,8-endomethylene in different concentrations of hydrazine solutions Fluorescence Spectrum Properties of Quinazolin-2-amine

[0044] 4-(4'-dimethylaminophenyl)-8,9,9-trimethyl-5,6,7,8-tetrahydro-5,8-methanoquinazole obtained in Example 1 Phenyl-2-amine was formulated as 1 x 10 -5 M of PBS buffer solution (10mM, pH=7.4, 10% (v / v) ethanol), hydrazine is dissolved in the PBS buffer solution and is made into concentration and is 0,5,10,15,20,25,30,35, 40, 45, 50 μM solutions. Measured different concentrations of hydrazine to 4-(4'-dimethylaminophenyl)-8,9,9-trimethyl-5,6,7,8-tetrahydro-5,8-methanoquinone The fluorescence emission spectrum of oxazolin-2-amine, as figure 2 shown. The results showed that the fluorescence intensity of the compound at 451nm was significantly enhanced, indicating that the compound could react with hydrazine.

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Abstract

The invention discloses a camphor-based fluorescent probe for detecting hydrazine and a preparation method thereof. The camphor-based fluorescent probe is: 4-(4′-dimethylaminophenyl)-8,9,9-trimethyl-5,6,7,8-tetrahydro-5,8-endomethylene Quinazoline-2-amine. The present invention utilizes the natural renewable resource camphor as a raw material to condense with p-dimethylaminobenzaldehyde to generate 3-(4'-dimethylaminobenzylidene)-1,7,7-trimethylbicyclo[2.1.1 ]heptane-2-one; 3-(4′-dimethylaminobenzylidene)-1,7,7-trimethylbicyclo[2.1.1]heptane-2-one and then carry out condensation cyclization with guanidine hydrochloride , to obtain 4-(4'-dimethylaminophenyl)-8,9,9-trimethyl-5,6,7,8-tetrahydro-5,8-methanoquinazoline-2- amine. The compound can specifically react with hydrazine to emit significantly enhanced blue fluorescence, and can be used as a fluorescent probe for the detection of hydrazine, and has good practical value.

Description

technical field [0001] The invention belongs to the technical field of fine organic synthesis, and relates to a camphor-based fluorescent probe for detecting hydrazine and a preparation method thereof. Background technique [0002] Hydrazine is an important active base and strong reducing agent, widely used in the preparation of pesticides, photosensitizers, medicines, dyes, catalysts and emulsifiers. In addition, due to the explosive properties of hydrazine, it is also frequently used as a high-energy fuel in satellite, missile and rocket propulsion systems. Therefore, the widespread use of hydrazine inevitably causes air and water pollution, thereby bringing about various environmental problems. More seriously, once absorbed through the skin and lungs, hydrazine can cause severe damage to the lungs, liver, kidneys, and central nervous system. Compared with traditional detection methods, fluorescent probes have the advantages of high sensitivity, fast response time, simpl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/70C09K11/06G01N21/64
CPCC07D239/70C09K11/06C09K2211/1007C09K2211/1044G01N21/643
Inventor 杨益琴王忠龙王石发张燕徐徐谷文徐海军姜倩李明新王芸芸
Owner NANJING FORESTRY UNIV
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