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End-nitrated 3, 4-perylene dicarboxylate compound as well as synthesis method and application thereof

A technology of ester compounds and perylene dicarboxylates, which is applied in the preparation of nitro compounds, chemical instruments and methods, organic chemistry, etc., can solve problems such as less research

Pending Publication Date: 2021-05-11
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the derivatization mode of perylene compounds is generally modified at its bay position (i.e. 1,6,7,12 positions), and there are fewer studies on the modification at the end positions (i.e. 9,10 positions)

Method used

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  • End-nitrated 3, 4-perylene dicarboxylate compound as well as synthesis method and application thereof
  • End-nitrated 3, 4-perylene dicarboxylate compound as well as synthesis method and application thereof
  • End-nitrated 3, 4-perylene dicarboxylate compound as well as synthesis method and application thereof

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preparation example Construction

[0031] In a second aspect, the present invention provides a method for synthesizing a terminal nitrated 3,4-perylene dicarboxylate compound, comprising the steps of:

[0032] Dissolving 3,4-perylene dicarboxylate compounds in a non-polar organic solvent, adding nitric acid or nitric acid solution dropwise under low temperature conditions, stirring and reacting; the 3,4-perylene dicarboxylate compounds are 3,4-perylene dicarboxylate or 1,6-bis(phenol)-3,4-perylene dicarboxylate compounds;

[0033] After the reaction is completed, the reaction mixture is separated and purified to obtain terminal nitrated 3,4-perylene dicarboxylate compounds.

[0034] In some embodiments, the nitric acid or nitric acid solution is added dropwise at a temperature of 0-20°C.

[0035] For 1,6-bis(phenolic)-3,4-perylenedicarboxylate, when the reaction temperature is controlled at 0-10°C, a mononitration reaction will occur, that is, a nitro group is connected at the 9-position, and the temperature i...

Embodiment 1

[0062] 200 mg of n-butyl 3,4-perylenedicarboxylate was dissolved in 20 ml of dichloromethane, and 2 ml of 2% fuming nitric acid in dichloromethane was added dropwise at 0° C., followed by TLC until the end of the reaction. The reaction solution was washed 3 times with water, and dried after removing the solvent. The crude product was separated by silica gel column chromatography, and the eluent was dichloromethane. Obtain 9-nitro-3,4-perylene dicarboxylic acid n-butyl ester (product A structure sees attached figure 1 Shown) 144 mg, yield 65%.

Embodiment 2

[0064] 200 mg of n-butyl 3,4-perylenedicarboxylate was dissolved in 20 ml of dichloromethane, and 1.5 ml of 5% fuming nitric acid in dichloromethane was added dropwise at room temperature, followed by TLC until the reaction was completed. The reaction solution was washed 3 times with water, and dried after removing the solvent. The crude product was separated by silica gel column chromatography, and the eluent was dichloromethane. Obtain 1,6-dinitro-3,4-perylene dicarboxylate n-butyl (product B-1 structure sees attached figure 2 , 3 Shown) 127 mg, yield 53%.

[0065] Take 120 mg of n-butyl 1,6-dinitro-3,4-perylenedicarboxylate and dissolve it in 8 ml of NMP, add 300 mg of p-tert-butylphenol, 90 mg of anhydrous potassium carbonate, catalytic amount KI, argon Under air protection, the reaction was stirred at 80°C for 12 hours. After the reaction, the reaction liquid was poured into 200 ml of 10% hydrochloric acid aqueous solution, suction filtered, and vacuum-dried to obtai...

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Abstract

The invention discloses an end-nitrated 3, 4-perylene dicarboxylate compound as well as a synthesis method and application thereof. The structural formula of the compound is shown in the specification, in the formula, R1 and R2 are the same or different alkyl with no more than 12 carbon atoms; R3 and R4 are hydrogen atoms, phenolic groups or substituted phenolic groups; and X is nitryl or hydrogen atom. The synthesis method has the advantages of mild reaction conditions, easiness in separation, simple method, high yield and the like, and the synthesized end-nitrated 3, 4-perylene dicarboxylate compound has stronger fluorescence characteristic, has better solubility than common perylene derivatives, and is almost soluble in all common organic solvents.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a terminal-nitrated 3,4-perylene dicarboxylate compound and a synthesis method and application thereof. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Perylene compounds are widely used in organic photoelectric materials, nanomaterials, artificial ion receptors, fluorescent molecular probes and other fields due to their good optical, thermal and chemical stability. At the same time, its fluorescence quantum yield is high, and it is a kind of fluorophore with excellent performance. Perylene carboxylate compounds have good absorption in the visible region...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/57C07C201/08C09K11/06
CPCC07C205/57C09K11/06C09K2211/1011
Inventor 石志强纪文杰郝冲
Owner SHANDONG NORMAL UNIV
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