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Preparation method of reduction-state ionic salt of perylene bisimide and derivative thereof

A perylene imide and derivative technology, applied in the field of organic matter and its synthesis, can solve the problems of high cost, harsh requirements, unsuitable for industrialization, etc., and achieve the effect of cheap price, high reaction yield, and easy availability of raw materials

Active Publication Date: 2016-07-06
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 reduction-state ionic salt of perylene bisimide and derivative thereof
  • Preparation method of reduction-state ionic salt of perylene bisimide and derivative thereof
  • Preparation method of reduction-state ionic salt of perylene bisimide and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Add 2.14 g of 3,4,9,10-perylenetetracarboxylic dianhydride (PTDA) (M=392) into 18 mL of concentrated (98%) H 2 SO 4 (M=98, 1.836g / mL) in a three-necked flask, oscillated by 35Hz ultrasonic waves for 10min, then placed it on a heat-collecting constant temperature magnetic stirrer and added a condensing device, stirred at room temperature for 6h, and then adjusted the temperature to 80 ℃, reflux reaction, adding 0.053gI 2 (M=127) was used as a catalyst and about 0.577mL (3.12g / mL) of liquid bromine (M=160) was slowly added dropwise into it using a constant pressure dropping funnel. After reacting for 24 hours, dilute the reaction solution with concentrated sulfuric acid to 60% with distilled water, then suction filter to obtain a filter cake, and dry the filter cake in a vacuum 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, add respectively 0....

Embodiment 2

[0054] Add 2.09 g of 3,4,9,10-perylenetetracarboxylic dianhydride (PTDA) (M=392) into 18 mL of concentrated (98%) H 2 SO 4 (M=98, 1.836g / mL) in a three-necked flask, oscillated by 35Hz ultrasonic waves for 10min, then placed it on a heat-collecting constant temperature magnetic stirrer and added a condensing device, stirred at room temperature for 6h, and then adjusted the temperature to 80 ℃, reflux reaction, adding 0.052gI 2 (M=127) was used as a catalyst, and 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 reacting for 24 hours, dilute the reaction solution with concentrated sulfuric acid to 60% with distilled water, then suction filter to obtain a filter cake, and dry the filter cake in a vacuum 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 respectively ...

Embodiment 3

[0060] Add 1.98 g of 3,4,9,10-perylenetetracarboxylic dianhydride (PTDA) into 18 mL of concentrated (98%) H 2 SO 4 In a three-necked flask, oscillate with 35Hz ultrasonic waves for 10min, then place it on a heat-collecting constant temperature magnetic stirrer and add a condensing device, stir at room temperature for 6h, adjust the temperature to 80°C, reflux reaction, and add 0.052gI 2 As a catalyst, about 0.58 mL of liquid bromine was slowly added dropwise into it with a constant pressure dropping funnel. After reacting for 24 hours, dilute the reaction solution with concentrated sulfuric acid to 60% with distilled water, then suction filter to obtain a filter cake, and dry the filter cake in a vacuum 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 bromoperylenetetraanhydride prepared by the above steps, 0.52mL of 17.5mol / L catalyst ac...

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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 compound and a synthesis method thereof. Background technique: [0002] Perylene imide and its derivatives have good photothermal stability, light absorption characteristics and high fluorescence quantum yield. Perylene imide and its derivatives are widely used in optical materials such as organic solar cells and field effect transistors. [0003] However, the preparation and application of ionic salts of peryleneimide and its derivatives are relatively few, or 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, the cost is high, and they are not suitable for industrialization. Invention content: [0004] The object of the present invention is to provide ...

Claims

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Application Information

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Patent Type & Authority Applications(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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