Synthetic method and micrometer wire preparation method of perylene bisimide derivative

A technology of perylene imide and synthesis method, which is applied in the fields of synthesis of perylene imide derivatives and preparation of micron wires, can solve problems such as no reports, and achieve the effects of high product purity, few by-products and high yield

Inactive Publication Date: 2016-02-03
SHANDONG JIANZHU UNIV
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Problems solved by technology

Therefore, it is very important to carry out the derivatization reaction of perylene imide compounds, among which the synthesis of perylene imide derivatives containing heteroatom rings at the b position is an important derivatization method, which can effectively tune the photoelectricity of such derivatives. performance, increase the conjugated π system of perylene derivatives, thereby changing the force between perylene molecules, such as van der Waals force, heteroatom-hetero

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  • Synthetic method and micrometer wire preparation method of perylene bisimide derivative
  • Synthetic method and micrometer wire preparation method of perylene bisimide derivative
  • Synthetic method and micrometer wire preparation method of perylene bisimide derivative

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Embodiment Construction

[0022] The present invention is further illustrated by the following examples.

[0023] The synthetic method of described perylene imide derivative:

[0024] 1-NO 2 -3,4; 9,10-perylenetetracarboxylic acid diimide (0.6g, 1mmol) was dissolved in 60mL of N-methylpyrrolidone, under vigorous stirring, heated at 180°C for 5 hours, and the reacted solution After cooling, drop it into 500mL hydrochloric acid solution with a concentration of 2moL / L to precipitate a precipitate, vacuum filter the precipitate, wash the solid with distilled water, and dry it in vacuum. phase, purified by silica gel column chromatography to obtain 0.34 g of a bright yellow solid product with a yield of 60%. 1 H-NMR (CHCl 3 , TMS, ppm): δ=8.95 (d, 2H), 8.83 (d, 4H), 5.16 (m, 2H), 2.66-2.63 (m, 4H), 1.94-1.55 (m, 8H), 1.41-1.26 (m, 8H). 13 CNMR (75MHz, CDCl 3 , ppm): δ=164.78, 163.74, 154.15, 133.93, 130.38, 126.46, 125.03, 124.36, 119.34, 54.50, 29.27, 26.65, 25.48.FT-IR (KBr, cm -1 ): v=2922, 1689, ...

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Abstract

The invention relates to a synthetic method and a micrometer wire preparation method of a perylene bisimide derivative. The synthetic method of the perylene bisimide derivative comprises the step of dissolving 1-NO2-3,4 and 9,10-perylene tetracarboxylic acid imidodicarbonic diamide into a polarity organic solvent, stirring and reacting for 4 to 6h at the temperature of 150 to 180 DEG C, dropping a solution after reacting into diluted hydrochloric acid, separating out precipitation, filtering, washing, drying and purifying to obtain a product. Dissolving the perylene bisimide derivative into a chloroformic solution, and preparing into 2x10<-3>mol/L of concentrated solution, taking 2mL of the to-be-used concentrated solution into a test tube, injecting 3 to 5mL of methanol solution into the test tube, and standing for one day, so as to obtain the micrometer wire corresponding to the perylene bisimide derivative. The synthetic method of the compound is simple, the cost is relatively low, the reaction is finished by one step, and the product purity is relatively high. An oxygen atom five-membered ring is introduced in a bay position, so that the conjugate pi system of the plane part of a perylene molecule is increased, and the acting force among the perylene molecules is changed, so that the preparation of the micrometer wire is realized.

Description

technical field [0001] The invention relates to a method for synthesizing perylene imide derivatives and micron wires, and belongs to the technical field of organic synthesis. Background technique [0002] Perylene imide derivatives have extremely high fluorescence quantum yield, good photothermal stability, unique photoelectric properties and redox properties, so they are widely used in organic field effect transistors, optoelectronic materials, organic solar cells, light emitting diodes And liquid crystal materials and other fields, it is a kind of recognized organic dye with extremely high utilization value. Therefore, it is extremely important to perform derivatization reactions on peryleneimide compounds, among which the synthesis of peryleneimide derivatives containing heteroatom rings at the Bay position is an important derivatization method, which can effectively tune the optoelectronic properties of such derivatives. performance, increase the conjugated π system of...

Claims

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Application Information

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IPC IPC(8): C07D491/16B82Y40/00
CPCB82Y40/00C07D491/16
Inventor 马永山张安东张超吴俊森
Owner SHANDONG JIANZHU UNIV
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