Method for preparing sulfur heterocyclic condensed naphthalimide derivants in one-pot method
A technology of naphthalene diimide and sulfur heterocycle, which is applied in the field of one-pot preparation of sulfur heterocycle fused naphthalene diimide derivatives, which can solve the problem of low yield or only a small amount of product or no product products, the inability to achieve effective synthesis of compounds, long synthesis steps, etc., to achieve the effects of rich variety, easy synthesis and preparation, and low synthesis cost
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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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