Reduced ionic salt of perylene bisimide and derivative of perylene bisimide and preparation method

A technology of perylene imide and derivatives is applied in the field of organic compounds and their electrochemical preparation, which can solve problems such as harsh requirements for raw materials and synthesis conditions, and achieve the effects of good air stability, strong stability and easy availability of raw materials.

Inactive Publication Date: 2017-03-22
YANSHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] At present, there is relatively little information on the preparation of environmentally stable reduced peryleneimides and their derivatives, and the preparation process of environmentally unstable peryleneimide ionic salts is limited to the reduction of sodium thiosulfate, electrochemical Reduction and C / Pd-H 2 Reduction, electrochemical reduction, and these preparation processes have strict requirements on raw materials and synthesis conditions, and can only be applied to scientific research under vacuum nitrogen protection conditions; the preparation process of air-stable peryleneimide ionic salts is limited to Potassium Carbonate Reduction at 80°C

Method used

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  • Reduced ionic salt of perylene bisimide and derivative of perylene bisimide and preparation method
  • Reduced ionic salt of perylene bisimide and derivative of perylene bisimide and preparation method
  • Reduced ionic salt of perylene bisimide and derivative of perylene bisimide and preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] 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 0.053g I 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.

[0045] In a 100ml three-necked reaction flask, add respectively 0....

Embodiment 2

[0050] 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 0.052g I 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.

[0051] In a 100ml three-necked reaction flask, add respectively...

Embodiment 3

[0056] 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, it was vibrated by 35Hz ultrasonic waves for 10min, then placed on a heat-collecting constant temperature magnetic stirrer and equipped with a condensing device, after stirring at room temperature for 6h, the temperature was adjusted to 80°C, and reflux reaction was added during which 0.052g I 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.

[0057] In a 100ml three-necked reaction flask, add 0.95g of bromoperylenetetraanhydride prepared by t...

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Abstract

The invention relates to a reduction state of perylene bisimide and a derivative of the perylene bisimide and a preparation method. Perylene-3,4,9,10-tetracarboxylic acid dianhydride is adopted as a raw material, and the perylene bisimide derivative with the low LUMO energy level and excellent photoelectric property is obtained through a bromination reaction, an amidation reaction and a nucleophilic substitution reaction in a synthesis manner; and then under the condition of the normal temperature, a first reduction potential is applied through an electrochemical method to easily obtain an air stable perylene bisimide radical anion through synthesis. The method for preparing perylene bisimide ionic salt is novel, unique, simple and high in yield and can achieve industrialization, and the effect is good; and materials of this kind have high stability on air in the reduction state, the science difficult problems are solved, and practical application is facilitated.

Description

technical field [0001] The invention relates to an organic substance and an electrochemical preparation method thereof. [0002] Background technique: [0003] Reduced peryleneimides have potential value and bright prospects in semiconductor materials and optoelectronic applications due to their near-infrared absorption properties and high electron mobility. [0004] At present, there is relatively little information on the preparation of environmentally stable reduced peryleneimides and their derivatives, and the preparation process of environmentally unstable peryleneimide ionic salts is limited to the reduction of sodium thiosulfate, electrochemical Reduction and C / Pd-H 2 Reduction, electrochemical reduction, and these preparation processes have strict requirements on raw materials and synthesis conditions, and can only be applied to scientific research under vacuum nitrogen protection conditions; the preparation process of air-stable peryleneimide ionic salts is limited ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/04C25B3/25
CPCC25B3/25
Inventor 张海全何恩方王建敏
Owner YANSHAN UNIV
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