Preparation method of reduced ionic salt of peryleneimide and its derivatives

A technology of perylene imide and derivatives, applied in the field of organic compounds and their synthesis, can solve the problems of harsh requirements, unsuitable industrialization, high cost, and achieve the effects of low price, easy availability of raw materials and high reaction yield

Active Publication Date: 2019-05-28
YANSHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Moreover, these preparation processes have strict requirements on raw materials and synthesis conditions, the cost is high, and they are not suitable for industrialization.

Method used

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  • Preparation method of reduced ionic salt of peryleneimide and its derivatives
  • Preparation method of reduced ionic salt of peryleneimide and its derivatives
  • Preparation method of reduced ionic salt of peryleneimide and its derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Add 2.14g of 3,4,9,10-perylenetetracarboxylic dianhydride (PTDA) (M=392) to the 18mL concentrated (98%) H 2 SO 4 (M=98,1.836g / mL) in a three-necked flask, vibrate with 35Hz ultrasonic for 10min, then place it on a heat-collecting thermostatic magnetic stirrer and add a condenser. After stirring at room temperature for 6h, adjust the temperature to 80 ℃, reflux reaction, during which 0.053g I was added 2 (M=127) As a catalyst, about 0.577 mL (3.12 g / mL) of liquid bromine (M=160) was slowly added dropwise into it using a constant pressure dropping funnel. After 24 hours of reaction, the reaction solution was diluted with distilled water to 60% concentrated sulfuric acid and filtered with suction to obtain a filter cake. The filter cake was dried in a vacuum drying oven at 90°C for 24 hours. The filter cake mainly contains the aforementioned three compounds a, b, and c, where a:b:c=7:2:1.

[0049] In a 100ml three-necked reaction flask, 0.89g of bromoperylenetetracarboxylic a...

Embodiment 2

[0054] Add 2.09g of 3,4,9,10-perylenetetracarboxylic dianhydride (PTDA) (M=392) to the 18mL concentrated (98%) H 2 SO 4 (M=98,1.836g / mL) in a three-necked flask, vibrate with 35Hz ultrasonic for 10min, then place it on a heat-collecting thermostatic magnetic stirrer and add a condenser. After stirring at room temperature for 6h, adjust the temperature to 80 ℃, reflux reaction, during which 0.052g I was added 2 (M=127) As a catalyst, about 0.58 mL (3.12 g / mL) of liquid bromine (M=160) was slowly added dropwise into it using a constant pressure dropping funnel. After 24 hours of reaction, the reaction solution was diluted with distilled water to 60% concentrated sulfuric acid and filtered with suction to obtain a filter cake. The filter cake was dried in a vacuum drying oven at 90°C for 24 hours. The filter cake mainly contains the aforementioned three compounds a, b, and c, where a:b:c=7:2:1.

[0055] In a 100ml three-necked reaction flask, add 0.91g of bromoperylenetetracarboxyli...

Embodiment 3

[0060] Add 1.98g of 3,4,9,10-perylenetetracarboxylic dianhydride (PTDA) to 18mL of concentrated (98%) H 2 SO 4 In a three-necked flask with 35Hz ultrasonic vibration for 10min, place it on a heat-collecting thermostatic magnetic stirrer and add a condensing device. After stirring for 6h at room temperature, adjust the temperature to 80℃, reflux reaction, and add 0.052g I 2 As a catalyst, about 0.58 mL of liquid bromine was slowly added dropwise into it using a constant pressure dropping funnel. After 24 hours of reaction, the reaction solution was diluted with distilled water to 60% concentrated sulfuric acid and filtered with suction to obtain a filter cake. The filter cake was dried in a vacuum drying oven at 90°C for 24 hours. The filter cake mainly contains the aforementioned three compounds a, b, and c, where a:b:c=7:2:1.

[0061] In a 100ml three-necked reaction flask, add 0.95g of bromoperylenetetracarboxylic anhydride prepared by the above steps, 0.52mL of 17.5mol / L cataly...

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Abstract

The invention discloses the reduction-state ionic salt of perylene bisimide and a derivative thereof as well as a preparation method. The preparation method comprises the following steps: with perylene-3,4,9,10-tetracarboxylic acid dianhydride as a raw material, synthesizing a perylene bisimide derivative with low LUMO energy level and excellent photoelectric performance through a bromination reaction, an amidation reaction and a nucleophilic substitution reaction; and synthesizing the perylene bisimide monovalent ionic salt with stable environment relatively easily according to the benzoquinone type transformation mechanism in an alkaline condition (organic base such as triethylamine, and inorganic base such as potassium carbonate). The method for synthesizing the perylene bisimide ionic salt is novel, unique and simple and realizes high yield; industrialization can be implemented while the effect is good; and moreover, the material in a reduction state responds to metal ions and acids different in oxidability.

Description

Technical field [0001] The invention relates to an organic substance and a method for synthesizing the same. Background technique: [0002] Perylene imide and its derivatives have good photothermal stability, light absorption properties and high fluorescence quantum yield. Peryleneimide and its derivatives are widely used in optical materials such as organic solar cells and field effect transistors. [0003] However, there are relatively few preparations and applications of ionic salts of perylene imides and their derivatives, and they are even blank. According to the latest report, the preparation process of the ionic salt of perylene imide is limited to the reduction with sodium thiosulfate, electrochemical reduction and C / Pd-H 2 reduction. Moreover, these preparation processes have strict requirements on raw materials and synthesis conditions, and the cost is high, which is not suitable for industrialization. Summary of the invention: [0004] The purpose of the present invent...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/06
CPCC07D471/06
Inventor 张海全何恩方王建敏王海龙
Owner YANSHAN UNIV
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