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Water-soluble perylene diimide derivatives containing N-pyridine oxide groups and synthetic method thereof

A technology for oxidizing pyridine groups and pyridyl groups, which is applied in the field of water-soluble perylene imide derivatives and their synthesis, can solve the problems of high cost of target compounds, low fluorescence quantum yield, damage to equipment, etc., and achieve low toxicity, The effect of high fluorescence quantum yield and mild reaction

Inactive Publication Date: 2010-05-12
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Although the water solubility of the above-mentioned compounds has been improved to a certain extent, the fluorescent quantum yields of these compounds in water are low, and there are different problems in the synthesis process, such as the use of concentrated sulfuric acid, which damages the reaction equipment and causes serious pollution; Raw materials such as methyl iodide with high price, low boiling point and high toxicity are used, so that the cost of the obtained target compound is too high, and strict labor protection measures are required

Method used

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  • Water-soluble perylene diimide derivatives containing N-pyridine oxide groups and synthetic method thereof
  • Water-soluble perylene diimide derivatives containing N-pyridine oxide groups and synthetic method thereof
  • Water-soluble perylene diimide derivatives containing N-pyridine oxide groups and synthetic method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] 1,7-bis(3-pyridyloxy)-N,N'-dicyclohexyl-3,4:9,10-perylene diimide preparation (synthetic route see figure 1 ):

[0031] Add 2.00 grams of 3,4:9,10-perylenetetracarboxylic dianhydride and 30 milliliters of cyclohexylamine to a 100 milliliter reaction flask, heat and reflux under vigorous stirring until the solid is completely dissolved, and evaporate the excess cyclohexylamine under reduced pressure for about 40 hours. Hexylamine was recovered and dried to obtain 2.70 g of the product N,N'-dicyclohexyl-3,4:9,10-perylenetetracarboxylic acid diimide, with a yield of 96%;

[0032] Add 2.00 g of N,N'-dicyclohexyl-3,4:9,10-perylenetetracarboxylic acid diimide and 150 ml of dichloromethane to a 250 ml reaction bottle, then add 30 ml of 10 gram of bromine in dichloromethane solution, heated and refluxed for 4 days under the protection of argon, cooled to room temperature, and the mixed solution of dichloromethane and bromine was evaporated under normal pressure for recovery, s...

Embodiment 2

[0039] Preparation of 1,6,7,12-tetra-tert-butylphenoxy-N,N'-bis(4-oxypyridinyl)-3,4:9,10-perylenetetracarboxylic acid diimide (synthetic route see figure 2 ):

[0040] Add 1.00 g of 1,6,7,12-tetrachloro-N, N'-dicyclohexyl-3,4:9,10-tetracarboxylic acid diimide, 1.74 g of tert-butyl Phenol, then add 0.97 grams of potassium carbonate, 20 milliliters of N-methylpyrrolidone (NMP), react at 110 ° C for 24 hours, cool to room temperature, pour the solution into 150 milliliters of 20% HCl solution, let stand overnight, filter with suction, wash with water until Neutral, then washed with a small amount of methanol, dried, and separated by column chromatography, dichloromethane: petroleum ether = 1: 1 as eluent, to obtain 1.07 g of product 1,6,7,12-tetra-tert-butylphenoxy -3,4: 9,10-perylenetetracarboxylic acid diimide, yield 65%;

[0041] Add 0.50 g of 1,6,7,12-tetra-tert-butylphenoxy-N,N'-dicyclohexyl-3,4:9,10-perylenetetracarboxylic diimide to a 50 ml reaction bottle Amine, 30 m...

Embodiment 3

[0047] 1,7-bis(3-pyridyloxy)-N,N'-bis(4-nitrooxypyridyl)-3,4:9,10-perylenetetracarboxylic acid diimide (synthetic route see image 3 ):

[0048] Add 0.70 g of 1,7-dibromo-N, N'-dicyclohexyl-3,4:9,10-tetracarboxylic acid diimide, 0.55 g of m-hydroxypyridine, and then add 0.81 gram of potassium carbonate, 20 milliliters of N-methylpyrrolidone (NMP), reacted for 24 hours at 80° C., cooled to room temperature, poured the solution into 150 milliliters of 20% (wt %) HCl solution, stood still overnight for suction filtration, and washed with water until neutral , washed with a small amount of methanol, dried, and separated by column chromatography, using dichloromethane: acetone = 20:1 as the eluent to obtain 702 mg of product 1,7-bis(3-pyridyloxy)-3,4:9 , 10-perylenetetracarboxylic acid diimide, yield 80%;

[0049] Add 0.60 g of 1,7-bis(3-pyridyloxy)-N,N'-dicyclohexyl-3,4:9,10-perylenetetracarboxylic acid diimide to a 50 ml reaction bottle, 30 ml Isopropanol, then add 1.36 g of p...

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Abstract

The invention discloses water-soluble perylene diimide derivatives containing N-pyridine oxide groups and a synthetic method thereof. In the general structural formula of the water-soluble perylene diimide derivatives containing N-pyridine oxide group, R'=OR or H, the substituents R are same or different and are independently selected from an N-pyridine oxide group or a hydrocarbon group, and at least one substituent R is an N-pyridine oxide group; and the hydrocarbon group is an alkyl group or aryl group. The water-soluble perylene diimide derivatives are oxidized with oxydol after halogenated perylene diimide derivatives react with a substituent reagent containing hydroxyl groups. The invention has the advantages of easily controlled preparation method and conditions, mild reaction, economical raw materials, small toxicity and high fluorescence quantum yield.

Description

technical field [0001] The invention relates to a class of water-soluble perylene imide derivatives and a synthesis method thereof, belonging to the technical field of organic synthesis. Background technique [0002] Perylene imides are rigid, planar, conjugated fused-ring macromolecules with good photochemical stability and strong fluorescence. They were mainly used as pigments or dyes in early research. Later, it was found that perylene imide compounds have good photoelectric activity, and can be applied in the fields of organic photoconductors, solar energy conversion, etc., which has aroused the interest of researchers in many high-tech application fields, and its applications have penetrated into color liquid crystal displays, And cutting-edge technology fields such as organic optoelectronic molecular devices. [0003] In recent years, such compounds have been used in the biological field, such as antiviral agents and cytostatic agents, etc., and their poor water solub...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K11/06
Inventor 石志强孙娟娟赵英杰冷传军张帅徐茂友
Owner SHANDONG NORMAL UNIV
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