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Perylenediimide compound, synthesis method and application in Fe3+ detection thereof

A perylene diimide and bisbromo perylene diimide technology, which is applied in the field of perylene diimide compounds, can solve the problems of expensive instruments and achieve the effects of low detection limit, simple synthesis and easy purification

Pending Publication Date: 2018-05-08
INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Relatively expensive for instrument requirements

Method used

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  • Perylenediimide compound, synthesis method and application in Fe3+ detection thereof
  • Perylenediimide compound, synthesis method and application in Fe3+ detection thereof
  • Perylenediimide compound, synthesis method and application in Fe3+ detection thereof

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Experimental program
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Effect test

Embodiment 1

[0041] (1) Synthesis of intermediate 1-bromo-7-p-tert-butylphenol-N,N-dicyclohexyl-3,4,9,10-perylenediimide

[0042] 1.065g (0.0015mol) of bisbromoperylenediimide, 0.269g (0.00195mol) of anhydrous potassium carbonate, and 0.181g (0.0012mol) of p-tert-butylphenol were added to the three-necked flask at one time, and then added to the three-necked flask Add 15ml of N-methylpyrrolidone, react at 145°C for 30min, stop the reaction, lower the temperature, pour the reactant into 1M hydrochloric acid solution, adjust the pH to 3, stir for 35min, filter, and dry in the air. Purified by column chromatography, using dichloromethane as eluent to collect the second band product. Chloroform / methanol recrystallization gave 0.571 g of red solid. NMR (300MHZ, CDCl 3 )δ:9.41(d,1H),8.59(d,1H),8.50(s,1H),9.14(d,1H),8.28(d,1H),7.92(s,1H),4.80(m,2H ),2.59(m,8H),1.99(m,8H),1.90(m,4H),0.94(s,9H).

[0043] (2) Synthesis of intermediate 1-piperazine-7-p-tert-butylphenol-N,N-dicyclohexyl-3,4,9,10-p...

Embodiment 2

[0055] (1) Synthesis of intermediate 1-bromo-7-p-tert-butylphenol-N,N-dicyclohexyl-3,4,9,10-perylenediimide

[0056] Add 1.061g (0.0015mol) of bisbromoperylenediimide, 0.2898g (0.0021mol) of anhydrous potassium carbonate, 0.225g (0.0015mol) of p-tert-butylphenol, and 12ml of N-methylpyrrolidone into a 50ml three-necked flask , react at 150°C for 45min, stop the reaction, lower the temperature, pour the reactant into 1M hydrochloric acid solution, adjust the pH value to 2.8, stir for 40min, filter, and dry in the air. Purified by column chromatography, using dichloromethane as eluent to collect the second band product. Chloroform / methanol recrystallization gave 0.593 g of red solid. NMR (300MHZ, CDCl 3 ) δ:9.41(d,1H),8.59(d,1H),8.50(s,1H),9.14(d,1H),8.28(d,1H),7.92(s,1H),4.80(m,2H ),2.59(m,8H),1.99(m,8H),1.90(m,4H),0.94(s,9H).

[0057] (2) Synthesis of intermediate 1-piperazine-7-p-tert-butylphenol-N,N-dicyclohexyl-3,4,9,10-perylenediimide

[0058] 0.781g (1mmol) 1-bromo-7...

Embodiment 3

[0064] (1) Synthesis of intermediate 1-bromo-7-p-tert-butylphenol-N,N-dicyclohexyl-3,4,9,10-perylenediimide

[0065] 1.072g (0.0015mol) of bisbromoperylenediimide, 0.33g (0.0024mol) of anhydrous potassium carbonate, and 0.27g (0.0018mol) of p-tert-butylphenol were added to the three-necked flask at one time, and then added to the three-necked flask Add 20ml of N-methylpyrrolidone, react at 140°C for 45min, stop the reaction, lower the temperature, pour the reactant into 1M hydrochloric acid solution, adjust the pH value to 3.1, stir for 30min, filter, and dry in the air. Purified by column chromatography, using dichloromethane as eluent to collect the second band product. Chloroform / methanol recrystallization gave 0.561 g of a red solid. NMR (300MHZ, CDCl 3 )δ:9.41(d,1H),8.59(d,1H),8.50(s,1H),9.14(d,1H),8.28(d,1H),7.92(s,1H),4.80(m,2H ),2.59(m,8H),1.99(m,8H),1.90(m,4H),0.94(s,9H).

[0066] (2) Synthesis of intermediate 1-piperazine-7-p-tert-butylphenol-N,N-dicyclohexyl-3,4...

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Abstract

The invention relates to a novel perylenediimide compound represented by the structural formula (I), a synthesis method and application thereof, and belongs to the field of chemical synthesis and ionanalysis. The perylenediimide compound has binding sites for Fe3+. The compound is prepared in a mixed solution of DMSO and deionized water and can detect ultraviolet spectrum changes of Fe3+, and detection limits and the sensitivity of the compound are high. Compared with the prior art, the synthesis method has the advantages of being simple to operate, more convenient in Fe3+ detection and the like, and has important application value. The structural formula (1) is shown in the description.

Description

technical field [0001] The present invention relates to the field of chemical synthesis and ion analysis, specifically a kind of perylene diimide compound, its synthesis method and its 3+ application in detection. Background technique [0002] Iron is a ubiquitous metal in cells, it plays a vital role in many life processes and plays an important role in many life activities. Such as electron transfer process, oxygen transport process, DNA and RNA synthesis, repair process and nitrogen fixation process by photosynthesis, etc. Fe 3+ It mainly exists in the form of protein binding in cells, but excess or deficiency can lead to serious disorders. Fe in living body 3+ Insufficient content will limit the delivery of oxygen to cells, resulting in fatigue, fatigue and low immunity; Fe 3+ Excessive content can catalyze the production of active oxygen ROS, and excessive active oxygen can damage esters, nucleic acids and proteins, thereby causing serious diseases, such as: Alzhei...

Claims

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Application Information

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IPC IPC(8): C07D471/06G01N21/33
CPCG01N21/33C07D471/06Y02E10/549
Inventor 王延风矫春鹏路文娟张平平吴忠玉刘爱芹蔡卓蓁赵艳婷张磊
Owner INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI