Cyclopentadiene-bridging dimeric perylene diimide compound and preparation method thereof

A bridging technology of bisperylene diimide and cyclopentadiene, which is applied in the fields of chemical instruments and methods, organic chemistry, organic dyes, etc., can solve the problems of complicated reaction steps, strict reaction conditions, and low reaction yield, etc. Achieve the effect of short reaction time, simple method and mild reaction conditions

Inactive Publication Date: 2014-05-28
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the general reaction steps of oligo-perylene diimide are complicated, the reaction conditions are strict, and the reaction yield is low. Generally, transition metal catalysts are required to participate in the reaction.

Method used

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  • Cyclopentadiene-bridging dimeric perylene diimide compound and preparation method thereof
  • Cyclopentadiene-bridging dimeric perylene diimide compound and preparation method thereof
  • Cyclopentadiene-bridging dimeric perylene diimide compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Take 600 mg of N,N'-dicyclohexyl-1-nitro-3,4:9,10-perylenetetracarboxylic diimide, 0.30 mL of cyclopentadiene and 415 mg of potassium carbonate dissolved in 20 mL of N -Methylpyrrolidone, stirred at room temperature, reacted for 2 hours, the reaction solution was dropped into 100 ml of 2mol / L dilute hydrochloric acid, precipitated, filtered with suction, 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. The product was obtained in 408 mg, yield 69%. Such as figure 1 , figure 2 As shown, by mass spectrometry and proton nuclear magnetic spectrum analysis of the product, it is determined that the perylene derivatives structural formula prepared by this method is as follows image 3 shown.

[0026]

Embodiment 2

[0028] Take 600 mg of N,N'-dicyclohexyl-1-nitro-3,4:9,10-perylenetetracarboxylic diimide, 0.30 mL of cyclopentadiene and 600 mg of potassium bicarbonate dissolved in 20 mL In the mixed solution of N,N'-dimethylacetamide and tetrahydrofuran (VN,N'-dimethylacetamide: V tetrahydrofuran = 1:1), stir at room temperature, react for 3 hours, and drop the reaction liquid into 100 ml In 2mol / L dilute hydrochloric acid, a precipitate precipitated, filtered with suction, washed with water three times, and dried. The crude product was subjected to silica gel column chromatography, and the eluent was dichloromethane:ethyl acetate=20:1. The product was obtained in 198 mg, yield 34%.

[0029]

Embodiment 3

[0031] Take 600 mg of N,N'-dicyclohexyl-1-nitro-3,4:9,10-perylenetetracarboxylic diimide, 0.30 mL of cyclopentadiene and 380 mg of sodium carbonate dissolved in 20 mL of N , N'-dimethylformamide, stirred and reacted at 50°C for 0.5 hours, the reaction liquid was dropped into 100 ml of 2mol / L dilute hydrochloric acid, precipitated, filtered with suction, 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. The product was obtained in 278 mg, yield 47%.

[0032]

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PUM

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Abstract

The invention discloses a cyclopentadiene-bridging dimeric perylene diimide compound and a preparation method thereof. The preparation method comprises the following specific steps: firstly, 1-nitro-3,4:9,10-perylentetracarboxylic diimide, cyclopentadiene and inorganic alkali salt are mixed and dissolved in a polar aprotic organic solvent and react for 0.5-3 hours to obtain a mixed solution; and then 2 mol / L diluted hydrochloric acid is added into the obtained mixed solution dropwise, a precipitate is precipitated and subjected to suction filtration, a coarse product is obtained after the precipitate is washed with water and subjected to silica-gel column chromatography to obtain a product, and the leaching liquid volume ratio of dichloromethane to ethyl acetate is 20: 1. The preparation method is simple in step, the product is obtained through one-step reaction, the cost is low, the reaction time is short, and the reaction conditions are mild.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a cyclopentadiene-bridged bisperylene diimide compound and a preparation method thereof. Background technique [0002] Perylene derivatives are a class of compounds with special structures, 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. Among them, dimerized and polymerized perylene diimide compounds, due to their better optical and electrical properties, have broad application prospects and are increasingly valued by researchers. However, the general react...

Claims

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Application Information

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IPC IPC(8): C07D491/22C09B5/62
CPCC07D491/22
Inventor 石志强张安东
Owner SHANDONG NORMAL UNIV
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