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Bay-site cyclization synthetic method of 3, 4:9, 10-perylenetetracarboxylic bisimide

A perylenetetracarboxylic acid diimide and a synthesis method technology are applied in the synthesis field of the cyclic reaction of the basal position, which can solve the problems of poor solubility and lower synthesis value, and achieve the avoidance of perylene plane distortion, simple reaction steps, Enriching the effect of derivatization methods

Inactive Publication Date: 2014-03-05
SHANDONG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The only way to maintain its planarity is to form a six-membered ring structure at the bay position. At present, transition metal-catalyzed cross-coupling is generally used to form new "carbon-carbon" bonds. This reaction requires anaerobic conditions or light conditions. Aromatic cyclization is carried out under the following two methods, and both methods form a larger aromatic structure, which makes the solubility worse and reduces the synthetic value

Method used

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  • Bay-site cyclization synthetic method of 3, 4:9, 10-perylenetetracarboxylic bisimide
  • Bay-site cyclization synthetic method of 3, 4:9, 10-perylenetetracarboxylic bisimide
  • Bay-site cyclization synthetic method of 3, 4:9, 10-perylenetetracarboxylic bisimide

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Experimental program
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Effect test

Embodiment 1

[0031] Take 600 mg of N,N'-dicyclohexyl-1-nitro-3,4:9,10-perylenetetracarboxylic acid diimide, 0.35 ml of diethyl malonate and 415 mg of potassium carbonate dissolved in 30 Milliliter of N-methylpyrrolidone, stirred at room temperature, reacted for 3 hours, the reaction solution was dropped into 100 ml of 2mol / L dilute hydrochloric acid, precipitated, suction filtered, washed 3 times with water, and dried. The crude product was subjected to silica gel column chromatography, and the eluent was dichloromethane:ethyl acetate=20:1. Obtain product A (structure sees attached figure 1 , 2 shown) 580 mg, 80% yield.

Embodiment 2

[0033] Take 600 mg of N,N'-dicyclohexyl-1-nitro-3,4:9,10-perylenetetracarboxylic acid diimide, 650 mg of 2,7-dibromofluorene and 415 mg of sodium carbonate in 30 ml of dioxane was reacted for 5 hours, cooled, and the reaction solution was dropped into 100 ml of 2mol / L dilute hydrochloric acid to precipitate a precipitate, filtered with suction, washed with water 3 times, and dried. The crude product was subjected to silica gel column chromatography, and the eluent was dichloromethane. Obtain product B (structure sees attached image 3 , 4 shown) 490 mg, yield 55%.

Embodiment 3

[0035] Take 645 mg of N,N'-dicyclohexyl-1,6-dinitro-3,4:9,10-perylenetetracarboxylic acid diimide, 0.4 ml of 2-nitropropane and 830 mg of potassium acetate In 30ml of N,N'-dimethylacetamide, heat to 60°C, react for 2.5 hours, cool down, drop the reaction liquid into 100ml of 2mol / L dilute hydrochloric acid, precipitate out, filter with suction, wash with water 3 times ,drying. The crude product was subjected to silica gel column chromatography, and the eluent was dichloromethane. Obtain product C (structure sees attached Figure 5 , 6 shown) 540 mg, yield 65%.

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Abstract

The invention relates to a bay-site cyclization synthetic method of 3, 4:9, 10-perylenetetracarboxylic bisimide. The method comprises the following steps: dissolving bay-site nitrified 3, 4:9, 10-perylenetetracarboxylic bisimide and a compound which can form carbanions in a polar aprotic organic solvent; adding an alkaline matter; stirring and reacting for 0.5-5 hours in a temperature range of 0-40 DEG C; dropwise adding the reacted liquid into diluted hydrochloric acid; separating out precipitates; and filtering, washing and drying to obtain the product. The method provided by the invention guarantees the planar structure of perylenetetracarboxylic bisimide to the maximum extent, and is mild in reaction condition and simple in reaction step. The obtained product is higher in yield which is basically over 50%, and the higher yield is over 80%.

Description

technical field [0001] The invention relates to a synthesis method of a novel 3,4:9,10-perylenetetracarboxylic acid diimide by a bay-position ring-forming reaction, belonging to the technical field of organic synthesis. Background technique [0002] Perylene derivatives are a class of compounds with a planar aromatic structure, which have excellent thermal stability, light stability, chemical stability and excellent dyeing performance. Since Kardo discovered perylene tetracarboxylic diimide compounds in 1913, these compounds have been widely used in the dye industry and coating industry. With the development, research and wide application of optoelectronic materials, perylene compounds have attracted more and more attention due to their excellent optoelectronic properties. Therefore, the research on the functional derivatization of perylene compounds has become particularly important. At present, the main derivatization reaction of perylene compounds is substitution reacti...

Claims

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Application Information

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IPC IPC(8): C07D491/22
CPCC07D491/22
Inventor 石志强张安东王永霞
Owner SHANDONG NORMAL UNIV
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