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N-unsubstituted thiophene isoindigo compound and preparation method thereof

A compound, the technology of isoindigo, which is applied in the field of N-unsubstituted thiophene isoindigo compounds and their preparation, can solve the problems of low synthesis efficiency and high cost, and achieve the effects of simple post-treatment, mild conditions and novel reaction routes

Inactive Publication Date: 2018-11-02
QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Synthesis of literature reports N - Various side chain substituted thiophene isoindigo compounds have the characteristics of low synthesis efficiency and high cost

Method used

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  • N-unsubstituted thiophene isoindigo compound and preparation method thereof
  • N-unsubstituted thiophene isoindigo compound and preparation method thereof
  • N-unsubstituted thiophene isoindigo compound and preparation method thereof

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Embodiment 1

[0044] Phenyl N -(thiophen-3-yl)-2,2-acetoxyacetamide (compound 2a)

[0045] At room temperature, 3-aminothiophene oxalate (18.92 g, 100 mmol) was added to a 100 mL reaction tube, dissolved in 50 mL of dry tetrahydrofuran, and cooled in an ice bath. After the reaction was cooled, 2,2-acetoxyacetyl chloride (21.40 g, 110 mmol, 1.1 eq.) was added dropwise, and the reaction was carried out under ice cooling for 30 min. Dissolved in ethyl acetate, washed with a large amount of water, then adjusted the pH to neutral with saturated aqueous sodium bicarbonate solution, and concentrated to obtain 15.44 g of crude yellow liquid of compound 2a, with a yield of 60%.

[0046] 1 H NMR (600 MHz, CDCl 3 ) δ 8.32 (s, 1H), 7.65 – 7.60 (dd, J = 2.9, 0.9Hz, 1H), 7.26 – 7.24 (dd, J = 5.1, 2.9 Hz, 1H), 7.06 (dd, J = 5.1, 0.9 Hz, 1H), 7.00 (s, 1H), 2.22 (s, 6H); 13 C NMR (151 MHz, CDCl 3 ) δ 168.58, 161.57, 133.97, 124.98, 121.01, 111.79, 85.20, 20.69.

[0047] ( Z / E )-2-(hydroxylamin...

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Abstract

The invention relates to an N-unsubstituted thiophene isoindigo compound and a preparation method thereof. The N-unsubstituted thiophene isoindigo compound adopts a structural general formula (I). According to the preparation method thereof, with 3-aminothiophene oxalate as a raw material, through a series of steps, such as acylation, condensation and cyclization, the N-unsubstituted thiophene isoindigo compound shown as the structural formula (I) is successfully obtained. The N-unsubstituted thiophene isoindigo compound can be used as an important synthesis block for preparing N-substituted thiophene isoindigo through N-side chain engineering, and has a good application prospect in the field of organic optoelectronic materials based on a thiophene isoindigo structure. (Refer to Specification).

Description

technical field [0001] The present invention relates to a N - Unsubstituted thiophene isoindigo compounds and preparation methods thereof, belonging to the field of heterocyclic compound synthesis and organic semiconductor materials. Background technique [0002] N -Replacing thiophene isoindigo compounds as important acceptor units to prepare various small molecules or polymer materials for the fields of organic field effect transistors, organic solar cells and other optoelectronic devices ( Adv. Mater ., 2016, 28, 3615-3645; Chem. ., 2015, 27, 6837-6847; J. Mater. Chem . A , 2015, 3, 9899-9908). It is precisely because of the potential application value of thiophene isoindigo compounds, N -The design and synthesis of various side chain substituted thiophene isoindigo compounds have aroused great interest of scientists. However, in the literature reports, the preparation of thiophene isoindigo compounds is firstly introduced into the starting material N -Alkyl sid...

Claims

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Application Information

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IPC IPC(8): C07D519/00
CPCC07D519/00
Inventor 万晓波张焕瑞蔡勉
Owner QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI