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Method for preparing sulfur heterocyclic condensed naphthalimide derivants in one-pot method

A technology of naphthalenediimide and sulfur heterocycle is applied in the field of preparing naphthalene diimide derivatives fused with sulfur heterocycle by one-pot method, which can solve the problem of low yield or only obtaining and trace product or not obtaining products, inability to achieve effective synthesis of compounds, long synthesis steps, etc., to achieve the effects of rich varieties, easy synthesis and preparation, and low synthesis costs

Active Publication Date: 2012-02-08
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

However, the synthesis steps of the NDI-DTYM2 series n-type organic semiconductor materials disclosed in the previous patents (CN200910197611.9, PCT / CN2010 / 077932) are relatively long, and are three-step reactions (the reaction steps are shown in the following formula), and the total product The yield is low (9%~20%), and it should be pointed out that the limitation of the three-step synthesis is relatively large, mostly limited to the preparation of NDI-DTYM2 derivatives substituted by N-alkyl groups, and N-aryl and N - Efficient synthesis of benzyl-substituted compounds (very low yield or only a small amount of product or no product), and the N-substituent should not be sensitive to acids (acetic acid, propionic acid, etc.) and reagents such as phosphorus tribromide

Method used

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  • Method for preparing sulfur heterocyclic condensed naphthalimide derivants in one-pot method
  • Method for preparing sulfur heterocyclic condensed naphthalimide derivants in one-pot method
  • Method for preparing sulfur heterocyclic condensed naphthalimide derivants in one-pot method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-9

[0056] (1) Example 1-9: Three-component one-pot preparation method of compound 1-9 (symmetrical N-substituted NDI-DTYM2 derivatives)

Embodiment 1

[0057] Example 1: N, N'-bis(2-octyl-dodecyl)-[2,3-d:6,7-d']-bis[2-(1,3-dithiacyclopenta Synthesis of alken-2-ylidene)-2-propanedicyano]-naphthalene-1,4,5,8-tetracarboxylic diimide (1).

[0058]

[0059] Concrete synthetic steps are:

[0060] Under nitrogen protection, 2,3,6,7-tetrabromonaphthalene tetracarboxylic dianhydride (TBNDA) (100mg, 0.17mmol) and 1,1-dicyanoethylene-2,2-dithiolate sodium (96mg , 0.52mmol) was added into 15mL DMF and heated to 50°C. After stirring for 1 h, 2-octyldodecylamine (204 mg, 0.68 mmol) was added, and the temperature was maintained for 7 h. Cool to room temperature, pour the reaction solution into 100 mL of saturated ammonium chloride solution, filter, wash the filter residue with water, dry in vacuo, use dichloromethane / petroleum ether (2:1) as eluent, and use a silica gel chromatography column to analyze the crude The product was separated and purified to obtain 52 mg of brown-red solid 3 with a yield of 28%. Mass Spectrum: MS (MALDI-T...

Embodiment 2

[0061] Example 2: N, N'-bis(2-decyl-tetradecyl)-[2,3-d:6,7-d']-bis[2-(1,3-dithiacyclopenta Synthesis of alken-2-ylidene)-2-propanedicyano]-naphthalene-1,4,5,8-tetracarboxylic diimide (2).

[0062]

[0063] Using 2-decyltetradecylamine instead of 2-octyldodecylamine, the synthesis method is the same as in Example 1 to obtain compound 2 as a brownish-red solid with a yield of 26%. Mass Spectrum: MS (MALDI-TOF) m / z 1214.9 (M + ); H NMR spectrum: 1 H-NMR (300MHz, CDCl 3 )δ (ppm): 0.848-0.889 (m, 6H, -CH 3 ), 1.232-1.311 (br, 40H, -CH 2 -), 2.013(m, 1H, CH), 4.222-4.247(d, 2H, J=7.2Hz, -CH 2 -N); Carbon NMR spectrum: 13 C-NMR (100Hz, CDCl 3 ):δ14.127,22.690,26.303,29.367,29.595,29.670,29.699,30.040,31.505,31.924,36.604,46.538,71.007,111.551,117.806,125.112,145.258,161.965(C=O),182.038(=CS 2 ).Elemental analysis calculation value (Anal.Calcd.For)C 70 h 98 N 6 o 4 S 4 : C, 69.15; H, 8.12; N, 6.91; Found: C, 69.36; H, 7.89; N, 6.78.

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Abstract

The invention relates to a method for preparing sulfur heterocyclic condensed naphthalimide derivants in a one-pot method. Tetrabromo naphthalic dianhydride, 2,2-dicyan-ethylene-1,1-bithiolate and organic amine are reacted in an organic solvent at the temperature of a room temperature to 80 DEG C, sulfur heterocyclic condensed naphthalimide derivants are prepared in the one-pot method, and the derivants can be symmetric N-substituent and asymmetric N-substituent compounds. The preparation method disclosed by the invention is easy to operate, has mild reaction conditions and strong universality, and can be used for preparing sulfur heterocyclic condensed naphthalimide high-performance n-type organic semiconductor materials with different N-substituent groups efficiently at low cost.

Description

technical field [0001] The invention relates to a preparation method of a class of high-performance n-type organic semiconductor materials, in particular to a one-pot preparation method of a class of sulfur heterocyclic fused naphthalene diimide derivatives having a chemical structure shown in the general formula , using this method, a simple and efficient one-pot synthesis of sulfur-heterocyclic fused naphthalene diimide derivatives with different N-substituents, where R 1 and R 2 Can be the same or different. [0002] Background technique [0003] Organic thin film transistors (OTFT) have the advantages of simple preparation process, low cost, light weight, flexibility, and good compatibility with plastic substrates. It is used in smart cards, electronic tags, electronic paper, active matrix Display, sensor, memory and other flexible electronic products have broad application prospects (Nature 2004, 428, 911-918.; Science 2009, 326, 1516-1519.; Nat.Mater.2010, 9, 859-...

Claims

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Application Information

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IPC IPC(8): C07D495/22
Inventor 高希珂狄重安胡云宾朱道本秦云科
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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