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4-propylamino-1,8-naphthalimide-7-benzo[c]acridine thiourea as well as preparation method and preparation thereof

A technology of naphthalimide and acridinium thiourea, which is applied in the field of organic fluorescent probes to achieve the effects of high yield, easy use and storage, and high selectivity

Active Publication Date: 2018-07-20
GUANGXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few effective silver ion-selective fluorescent probes, so it is very meaningful to develop high-sensitivity colorimetric and fluorescent probes for Ag+ detection

Method used

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  • 4-propylamino-1,8-naphthalimide-7-benzo[c]acridine thiourea as well as preparation method and preparation thereof
  • 4-propylamino-1,8-naphthalimide-7-benzo[c]acridine thiourea as well as preparation method and preparation thereof
  • 4-propylamino-1,8-naphthalimide-7-benzo[c]acridine thiourea as well as preparation method and preparation thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation method of described 4-propylamino-1,8-naphthalimide-7-benzo[c]acridinethiourea comprises the following steps:

[0034] Step 1. Add 1.34g of brominated 1,8-naphthalene anhydride and 20ml of 95% ethanol to a 50mL three-neck flask, add 2ml of hydrazine hydrate dropwise under stirring, stir at room temperature for 4.5h, and monitor the reaction with TCL. After the reaction, filter with suction and wash with 95% ethanol to obtain a dark green solid. The obtained dark green solid is recrystallized with chlorobenzene to obtain a light yellow solid, which is 4-bromo-1,8-naphthalimide, wherein, The detection and tracking reagents used in TLC are chloroform and methanol, and their volume ratio is 10:1.

[0035] Step 2: Add 0.1g of 4-bromo-1,8-naphthalimide, 0.5mL of propylamine, and 10ml of ethylene glycol methyl ether to a 50mL round-bottomed flask successively for reflux, and place in an oil bath within 10min Heated to 85°C in medium temperature, then continued...

Embodiment 2

[0038] The preparation method of described 4-propylamino-1,8-naphthalimide-7-benzo[c]acridinethiourea comprises the following steps:

[0039]Step 1. Add 1.44g of brominated 1,8-naphthalene anhydride and 30ml of 95% ethanol to a 50mL three-neck flask, add 3ml of hydrazine hydrate dropwise under stirring, stir at room temperature for 5.5h, and monitor the reaction with TCL. After the reaction, filter with suction and wash with 95% ethanol to obtain a dark green solid. The obtained dark green solid is recrystallized with chlorobenzene to obtain a light yellow solid, which is 4-bromo-1,8-naphthalimide, wherein, The detection and tracking reagents used in TLC are chloroform and methanol, and their volume ratio is 10:1.

[0040] Step 2: Add 0.2g of 4-bromo-1,8-naphthoimide, 1.5mL of propylamine, and 20ml of ethylene glycol methyl ether to a 50mL round-bottomed flask in turn for reflux, and place in an oil bath within 20min Heat to 90°C in medium temperature, then continue to heat t...

Embodiment 3

[0043] The preparation method of described 4-propylamino-1,8-naphthalimide-7-benzo[c]acridinethiourea comprises the following steps:

[0044] Step 1. Add 1.39g (5mmoL) of brominated 1,8-naphthalene anhydride and 20-30ml of 95% ethanol to a 50mL three-neck flask, and add 2.5ml (2.58mmoL) of hydrazine hydrate dropwise under stirring , stirred at room temperature for 5 hours, and monitored the reaction with TCL. After the reaction was completed, suction filtered and washed with 95% ethanol to obtain a dark green solid. The obtained dark green solid was recrystallized with chlorobenzene to obtain a light yellow solid, namely 4-bromo-1,8 -Naphthalimide, wherein the detection and tracking reagent used by TLC is chloroform and methanol, and its volume ratio is 10:1.

[0045] The yield of 4-bromo-1,8-naphthalimide was 81.36%, 1 H-NMR (CDCl 3 , 400MHz): 8.68(d, 1H, J=7.2Hz), 8.60(d, 1H, J=8.4Hz), 8.44(d, 1H, J=7.6Hz), 8.06(d, 1H, J=8.0Hz ), 7.87 (t, 1H, J=7.6Hz), 5.30 (s, 2H).

[0...

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Abstract

The invention discloses 4-propylamino-1,8-naphthalimide-7-benzo[c]acridine thiourea. The 4-propylamino-1,8-naphthalimide-7-benzo[c]acridine thiourea has a chemical structural formula represented by (III) shown in the description. The invention further provides a preparation method of the 4-propylamino-1,8-naphthalimide-7-benzo[c]acridine thiourea. The 4-propylamino-1,8-naphthalimide-7-benzo[c]acridine thiourea prepared by the method has very high selectivity to silver ions when the 4-propylamino-1,8-naphthalimide-7-benzo[c]acridine thiourea is applied to fluorescent probes, the maximum absorption peak presents at a position of 445nm, and the light absorbance is remarkably improved.

Description

technical field [0001] The present invention relates to the technical field of organic fluorescent probes, in particular to a 4-propylamino-1,8-naphthoimide-7-benzo[c]acridinethiourea, its preparation method and use, its preparation method and use. Background technique [0002] The relationship between metal ions and environmental science, life science, medicine and many other fields is very close, and its identification and detection also occupy an important position in analytical chemistry. Silver ion is one of the heavy metal ions that are threatening and toxic to human body and environment. Long-term exposure to silver in humans or animals can result in anemia, cardiac dilation, slow growth, embryotoxicity, and liver cirrhosis. Because silver is widely used in industrial production processes such as electroplating, metallurgy, and military industry, the detection of silver ions and the study of biological processes have become research hotspots in recent years. Fluore...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/18C09K11/06G01N21/64
CPCC07D221/18C09K11/06C09K2211/1029G01N21/643
Inventor 霍丽妮陈睿韦燕飞李培源贾智若卢澄生
Owner GUANGXI UNIV OF CHINESE MEDICINE