A kind of preparation method of dithiophenophthalimide

A technology of dithiophenophthalimide and phenophthalimide, which is applied in the field of organic compound synthesis, can solve the problems of less research on the application of dithiophenophthalimide, low yield, and severe toxicity. and other problems, to achieve the effect of high yield, no highly toxic substances, and short reaction time

Active Publication Date: 2020-12-01
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, there are few studies on the application of dithienophthalimide in the field of organic optoelectronics.
The reported synthetic methods, such as the one-step method (Journal of Heterocyclic Chemistry.DOI 10.1002 / jhet), have low yields and require nitrogen protection, and the use of titanium tetrachloride / tributylamine system is highly toxic, which limits the ability of dithiophene Wider application of aphthalimide in the field of organic optoelectronics

Method used

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  • A kind of preparation method of dithiophenophthalimide
  • A kind of preparation method of dithiophenophthalimide
  • A kind of preparation method of dithiophenophthalimide

Examples

Experimental program
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Effect test

Embodiment 1

[0023] 【Reaction route】

[0024]

[0025] According to the reaction route, 2-thiopheneglyoxylic acid (0.5g, 3.2mmol) and potassium hydroxide (196mg, 3.5mmol) were dissolved in 20mL of aqueous solution, the temperature was controlled at 100°C, the mixture was stirred and heated under reflux for 10h, and the aqueous solution was spin-dried after the reaction was completed. Product B is obtained. 1 HNMR (400MHz, DMSO-d6, δ, ppm): 7.89 (dd, J = 4.9, 0.8Hz, 1H), 7.71 (dd, J = 3.7, 0.8Hz, 1H), 7.17 (dd, J = 4.7, 3.9 Hz,1H).

Embodiment 2

[0027] 【Reaction route】

[0028]

[0029] Dissolve product B (100mg, 0.52mmol) and thiophene acetate (80mg, 0.6mmol) in 10mL of acetic anhydride solvent, control the temperature at 120°C, reflux, stir and heat for 12h, slowly pour into water after the reaction, and extract with saturated sodium chloride / After water, 100-200 mesh silica gel was used as the stationary phase, and petroleum ether / dichloromethane (volume ratio 3:1) was used as the eluent to pass through the column, and the product D was obtained after purification.

Embodiment 3

[0031] 【Reaction route】

[0032]

[0033] According to the reaction route, the product D (1g, 3.8mmol) was dissolved in 200mL of dichloromethane solution, and elemental iodine (100mg, 0.38mmol) was added as a catalyst. Mesh silica gel was used as the stationary phase, and petroleum ether / dichloromethane (system ratio 5:1) was used as the eluent to pass through the column for purification to obtain fused-ring dithiophene anhydride (E).

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Abstract

The invention discloses a preparation method of dithiophene acene diimide. The preparation method has the advantages that raw materials are simple and easy to obtain, reaction conditions are easy to control, and the reaction yield is high. The preparation method comprises the following steps that firstly, potassium glyoxylate is prepared from 2-glyoxylic acid and potassium hydroxide in an aqueoussolution of 80-100 DEG C, then the potassium glyoxylate and 2-acetic acid thiophene are dehydrated and condensed in acetic anhydride to form anhydride, then loop closing is carried out under the illumination catalysis, finally, imidization is carried out, and the dithiophene acene diimide is synthesized. The method has the advantages that the dithiophene acene diimide is synthesized by using a step-by-step method, anhydrous and oxygen-free conditions are not needed, a highly toxic tributylamine-titanium tetrachloride system is not needed, the reaction yield is high, purification is easy, and atechnical basis is provided for expanding the application range of the method in the fields of biology, chemistry, materials and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and in particular relates to a preparation method of dithienophthalimide. Background technique [0002] The n-type structural unit is fundamental to develop n-type semiconductors. Aromatic imides are one of the classical n-type structural units, which can exhibit relatively high electron affinity, high electron mobility, and excellent chemical, thermal, and photochemical stability. The aromatic nuclei are substituted by one or two groups of electron-deficient imide groups that are conjugated to each other. These materials are electron-deficient. For example, the widely used naphthalimides include perylene diimide and naphthalene diimide , and the simplest aromatic imide system is phthalimide and thiophene imide. Dithiophenophthalimides, as thiophene-like imides, have simple, compact, symmetrical and planar structures. It can facilitate the intermolecular interactions of plan...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/14
CPCC07D495/14
Inventor 赖文勇薛轶博李祥春黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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