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Asymmetric sulfur cyclization type perylene diimide derivative and preparation method thereof
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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 that have not been seen, and achieve the effects of excellent electron mobility and on-off ratio, single product structure, and mild reaction conditions
Inactive Publication Date: 2019-07-26
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 sulfur powder 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 sulfur powder 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
The invention belongs to the technical field of organic synthesis and discloses an asymmetric sulfur cyclization type perylenediimide derivative and a preparation method thereof. The asymmetric sulfur cyclization type perylenediimide derivative is characterized in that a perylenediimide harbor dinitration type derivative is used as a raw material, a sulfur source is added, catalysts are avoided, and heating in a solvent is performed to directly obtain a target product. An absorption spectrum of the derivative is high in red shift, a strong absorption peak is newly added at a position of 500-700nm, and complete planarity and excellent stability are achieved. According to the preparation method of the derivative, a target compound can be obtained only through one-step reaction. A productof the preparation method is single structurally, generation of symmetrical compounds is avoided, and the problem that perylene diimide derivatives in symmetrical structures are always generated in simultaneous ring closing of four harbor sites of perylene diimide is solved. Simplicity in product separation and purification is achieved, synthesis raw materials are convenient and easy to acquire, and easiness in industrial mass production is realized. The derivative is capable of serving as an organic semiconductor material to be applied to 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] Peryleneimide 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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