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3,4-perylene dicarboxylate compound, and synthetic method and applications thereof

A technology of ester compound and perylene dicarboxylic acid, which is applied in the field of 3,4-perylene dicarboxylate ester compound and its synthesis, can solve the problems of not being seen and few positions for continuing reaction, and achieve high selectivity, The effect of simple reaction steps and mild reaction conditions

Inactive Publication Date: 2016-03-16
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the research on the synthesis of perylene carboxylate derivatives mainly focuses on 3,4,9,10-perylene tetracarboxylate derivatives, and there are fewer positions for continued reaction. , Report on 4-perylenedicarboxylates and their synthesis methods and applications

Method used

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  • 3,4-perylene dicarboxylate compound, and synthetic method and applications thereof
  • 3,4-perylene dicarboxylate compound, and synthetic method and applications thereof
  • 3,4-perylene dicarboxylate compound, and synthetic method and applications thereof

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Experimental program
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Effect test

Embodiment 1

[0036] Dissolve 600 mg of n-butyl perylene-3,4-anhydride-9,10-perylenedicarboxylate in 30 ml of freshly distilled quinoline, add 500 mg of Cu 2 O, under anaerobic conditions, reflux reaction for 48 hours, pour the reacted solution into 100 milliliters of 0.1 mol / liter sulfuric acid aqueous solution to form a precipitate, suction filter, wash and dry to obtain a crude product. The crude product was subjected to silica gel column chromatography, and the eluent was dichloromethane. Product A was obtained in 367 mg, yield 61%.

[0037] The structural characterization of product A is as follows Figure 1-2 as shown,

[0038] The hydrogen spectrum is divided into three parts: chemical shift from 1 to 2, here is the hydrogen on the alkyl chain on the ester group in the 3,4-perylene dicarboxylate compound, from left to right is β, γ , δ hydrogen; 4 to 5 are the α hydrogen on the alkyl chain on the ester group; there are four groups of peaks between 7 and 9, of which 7.26 is CDCl 3...

Embodiment 2

[0041] Dissolve 600 mg of n-propyl perylene-3,4-anhydride-9,10-perylenedicarboxylate in 20 mL of freshly distilled quinoline, add 300 mg of Cu 2 O, under anaerobic conditions, reflux reaction for 40 hours, pour the reacted solution into 80 ml of 0.05 mol / L hydrochloric acid aqueous solution to form a precipitate, suction filter, wash, and dry to obtain a crude product. The crude product was subjected to silica gel column chromatography, and the eluent was dichloromethane. 378 mg of product B were obtained, yield 63%.

Embodiment 3

[0043] Dissolve 600 mg of n-pentyl perylene-3,4-anhydride-9,10-perylenedicarboxylate in 25 ml of freshly distilled quinoline, add 600 mg of Cu 2 O, under anaerobic conditions, reflux reaction for 52 hours, pour the reacted solution into 90 milliliters of 0.08 mol / liter nitric acid aqueous solution to form a precipitate, suction filter, wash and dry to obtain a crude product. The crude product was subjected to silica gel column chromatography, and the eluent was dichloromethane. 396 mg of product C were obtained, yield 66%.

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Abstract

The invention discloses a 3,4-perylene dicarboxylate ester compound, and a synthetic method and applications thereof. The structure of the 3,4-perylene dicarboxylate ester compound is represented by formula I, wherein R is used for representing hydrocarbon alkyl with 6 or fewer carbon atoms. The 3,4-perylene dicarboxylate ester compound possesses excellent fluorescence groups, and the benzene rings possess more reaction sites capable of realizing reaction with other substances. The synthetic method comprises following steps: a perylene-3,4-anhydride-9,10-perylene dicarboxylate compound is dissolved in quinoline; Cu2O is added; and the 3,4-perylene dicarboxylate ester compound is obtained via reflux reaction under oxygen-free conditions. The synthetic method is simple, is high in yield, and is suitable for industrialized production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to 3,4-perylene dicarboxylate compounds and their synthesis method and application. Background technique [0002] Carboxylate derivatives of perylene have excellent physical and chemical properties, have good absorption of light from the visible region to the infrared region, have a high fluorescence quantum yield, and have high solubility in common organic solvents , is a class of fluorophores with excellent properties. Molecular probes using perylene carboxylate derivatives as fluorophores have been widely used in the fields of biomedicine, biochemistry, and environmental science. Therefore, the research on the synthesis of carboxylate derivatives of perylene has become particularly important. At present, the research on the synthesis of perylene carboxylate derivatives mainly focuses on 3,4,9,10-perylene tetracarboxylate derivatives, and there are fewer positions for ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/76C07C67/30C09K11/06
CPCC07C67/30C07C69/76C09K11/06C09K2211/1011
Inventor 石志强王苒申涵
Owner SHANDONG NORMAL UNIV
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