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A class of asymmetric thiocyclized perylene imide derivatives and preparation method
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A perylene imide, asymmetric technology, applied in the field of organic semiconductor materials, can solve the problems such as perylene imide derivatives, and achieve excellent electron mobility and switch ratio, high yield and simple operation
Inactive Publication Date: 2021-06-11
DALIAN UNIV OF TECH
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[0005] So far, there is no asymmetric thiocyclized harbor position ring-closed perylene imide derivatives that can be synthesized in one step.
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[0066] Example 1: Preparation of 3-pentylamine-derived asymmetric thiocyclized peryleneimides
[0067]
[0068] Concrete synthetic steps:
[0069] (1) Add 0.6 g of sulfurpowder to a reaction flask containing 3.0 g of dinitro perylene imide, then add 15 ml of DMF, heat to 120° C., and react for 6 hours.
[0070] (2) After the reaction, cool down to room temperature, extract with dichloromethane, distill off the dichloromethane under reduced pressure, and separate by column to obtain 2.5 g of the product with a yield of 83%.
[0073] Example 2: Preparation of 6-undecylamine-derived asymmetric thiocyclized peryleneimide
[0074]
[0075] Concrete synthetic steps:
[0076] (1) Add 0.6 g of sulfurpowder to a reaction flask containing 7.4 g of dinitro perylene imide, then add 20 ml of toluene, heat to 100° C., and react for 10 hours.
[0077] (2) After the reaction, cool down to room temperature, extract with dichloromethane, distill off the dichloromethane under reduced pressure, and separate by column to obtain 5.9 g of the product with a yield of 80%. HRMS: found 791.0960.
[0079] Example 3: Preparation of 7-tridecylamine-derived asymmetric thiocyclized peryleneimides
[0080]
[0081] Concrete synthetic steps:
[0082] (1) Add 0.6 g of sulfur to a reaction flask containing 3.11 g of dinitro perylene imide, then add 15 ml of DMF, heat to 110° C., and react for 6 hours.
[0083] (2) After the reaction, cool down to room temperature, extract with dichloromethane, distill off the dichloromethane under reduced pressure, and separate by column to obtain 2.68 g of the product with a yield of 86%. HRMS: found 846.3559.
[0084] The TGA test shows that its thermal decomposition temperature is greater than 350°C, indicating good thermal stability.
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Abstract
A class of asymmetric thiocyclized peryleneimide derivatives and a preparation method thereof belong to the technical field of organic synthesis. This kind of asymmetric thiocyclized peryleneimide derivatives uses the peryleneimide port double-nitrated derivatives as raw materials, adds a sulfur source, and directly prepares the target product by heating in a solvent without a catalyst. The absorption spectrum of the derivative is greatly red-shifted, and a new strong absorption peak is added at 500-700nm, showing complete planarity and excellent stability. The preparation method of this kind of derivative only needs one-step reaction to obtain the target compound. The product of the preparation method has a single structure and no symmetrical compound is formed, which overcomes the problem that a symmetrical peryleneimide derivative is always produced when the four harbor positions of the beric imide are simultaneously closed. The separation and purification of the product is simple, the raw materials in the synthesis are convenient and easy to obtain, and it is easy to industrialize mass production. Such derivatives can be used as organic semiconductor materials in different fields.
Description
technical field [0001] The invention relates to a class of asymmetric thiocyclized perylene imide derivatives and a preparation method thereof, belonging to the field of organic semiconductor materials. Background technique [0002] Perylene imide is the abbreviation of 3,4,9,10-perylene tetracarboxylic acid diimide. The whole molecule is composed of a central perylene ring skeleton and two-sided dicarboxylic acid imides. Its advantages include: strong absorption in the visible light region, high molarextinction coefficient, fluorescencequantum yield, good photostability and thermal stability, etc. It is a class of organic semiconductor materials with excellent performance. [0003] The harbor position of peryleneimide is affected by the electron-withdrawing groups of the imides on both sides, so the reactivity is strong, and aromatic electrophilic substitution reaction is easy to occur, and active groups such as halogen or nitro can be introduced into the harbor of peryle...
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