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A class of metal tin cyclized perylene imide derivatives and its preparation method and application

A technology of perylene imide and metal tin is applied in the field of organic semiconductor materials to achieve the effects of simple structure, long triplet lifetime and simple synthesis method

Active Publication Date: 2021-06-15
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there has been no peryleneimide derivatives involving the harbor position ring closure of metal tin cyclization

Method used

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  • A class of metal tin cyclized perylene imide derivatives and its preparation method and application
  • A class of metal tin cyclized perylene imide derivatives and its preparation method and application
  • A class of metal tin cyclized perylene imide derivatives and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]

[0024] Weigh 1g of bromoperyleneimide, 1.9g of hexa-n-butylditin, 15mg of dibenzylideneacetone palladium dichloride, and 20mg of trimethylphenylphosphine in a reaction flask, add 5ml of toluene, and Stir for 6 hours. After the reaction was complete, the reaction solution was spin-dried under reduced pressure, and 0.6 g of product was obtained by column chromatography, with a yield of 48%, HRMS: found 762.2470.

Embodiment 2

[0026]

[0027] Weigh 1g of bromoperyleneimide, 3.36g of hexa-n-butylditin, 12mg of dibenzylideneacetone palladium dichloride, and 16mg of trimethylphenylphosphine in a reaction flask, add 5ml of toluene, and Stir and reflux for 3 hours. After the reaction was complete, the reaction solution was spin-dried under reduced pressure, and 0.5 g of the product was separated by column chromatography with a yield of 41%. HRMS (MALDI-TOF): Calculated for C54H70N2O4Sn M-, 930.4358, found 930.4310.

Embodiment 3

[0029]

[0030] Weigh 1g of bromoperyleneimide, 3.92g of hexa-n-butylditin, and 5mg of palladium acetate into a reaction flask, add 5ml of 1,4dioxane, and stir and reflux at 120°C for 3 hours. After the reaction was complete, the reaction solution was spin-dried under reduced pressure, and 0.48 g of product was obtained by column chromatography with a yield of 40%. HRMS (MALDI-TOF): found 3462.1625.

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Abstract

A kind of metal tin cyclized perylene imide derivatives and its preparation method and application belong to the field of organic semiconductor materials. This kind of metal tin cyclized perylene imide derivatives introduces metal tin into the harbor position of perylene imide derivatives through palladium catalysis to form a five-membered metal heterocycle. Research status of heterocycles formed by metals. The introduction of the metallic tin element makes the derivative more valuable for research in the field of photoelectric materials. As a photoelectric material, the derivative has great application prospects in the fields of solar cells, light-emitting diodes and organic field effect transistors. In addition, the introduction of the heavy element tin makes the derivative have a strong ability to generate a triplet state, which can be used as a new type of photosensitizer. The directly linked heavy metal tin improves the ability of peryleneimide to generate triplet states, and at the same time makes it have a longer triplet lifetime, providing a new scheme for metal element-modified peryleneimides as photosensitizers.

Description

technical field [0001] The invention relates to a class of metal tin cyclized perylene imide derivatives, a preparation method and an application thereof, which belong 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 molar extinction coefficient, fluorescence quantum yield, good photostability and thermal stability, etc. It is a class of organic semiconductor materials with excellent performance. 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 p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/22C09K11/06B01J31/22A61K41/00H01L51/30H01L51/46H01L51/54
CPCC07F7/2208C09K11/06B01J31/1825A61K41/0057B01J2231/70C09K2211/188H10K85/30Y02E10/549
Inventor 陈令成张文重肖义
Owner DALIAN UNIV OF TECH
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