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Diperylene-3,4,6,7:12,13,15,16-octocarboxylic tetraimides compounds and production method thereof

A technology of octacarboxylic tetraimide and tetracarboxylic diimide, which is applied to diperylene-3,4,6,7:12,13,15,16-octacarboxylic tetraimide In the field of compounds and their preparation methods, it can solve problems such as not being seen, and achieve the effects of simple synthesis methods, novel chemical structures, and high purity

Inactive Publication Date: 2009-05-06
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far, also do not see the biperylene-3,4,6,7:12,13,15,16-octacarboxylic acid tetraimide compound and its preparation method that contain sulfur atom or selenium atom report

Method used

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  • Diperylene-3,4,6,7:12,13,15,16-octocarboxylic tetraimides compounds and production method thereof
  • Diperylene-3,4,6,7:12,13,15,16-octocarboxylic tetraimides compounds and production method thereof
  • Diperylene-3,4,6,7:12,13,15,16-octocarboxylic tetraimides compounds and production method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1 (N, N', N", N"'-tetrakis(2,6-diisopropylphenyl)-thiabisperylene-3,4,6,7:12,13,15, 16-Octacarboxylic tetraimide and N,N',N",N"'-tetrakis(2,6-diisoendylphenyl)-dithiabiperylene-3,4,6,7 : 12,13,15,16-octacarboxylic acid tetraimide)

[0052]

[0053] Concrete synthetic steps are:

[0054] 1. Add 1mmol of N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic diimide , 10mmol sodium sulfide, 6mmol cuprous iodide, 7mmol L-proline and 12mmol anhydrous potassium carbonate are mixed together;

[0055] 2. Add 10ml dimethyl sulfoxide to the mixture prepared in step 1;

[0056] 3. Under nitrogen protection, heat the mixed solution prepared in step 2 to 110°C and react for 10 hours; after the reaction, the product is dissolved in ethyl acetate, washed with aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, The solvent was evaporated to dryness below 60°C, and the product N, N', N", N"'-tetrakis(2,6-diisopropylpheny...

Embodiment 2

[0057] N,N',N",N"'-tetrakis(2,6-diisopropylphenyl)-thiabiperylene-3,4,6,7:12,13,15,16-octacarboxylic The mass spectrogram of acid tetraimide is shown in Figure 1; , 6,7: The mass spectrum of 12,13,15,16-octacarboxylic acid tetraimide is shown in Figure 2; 1 The H-NMR figure is shown in Figure 3; 13 The C-NMR chart is shown in FIG. 4 . Example 2 (N, N', N", N"'-tetrakis(2,6-diisopropylphenyl)-selenobiperylene-3,4,6,7:12,13,15, 16-Octacarboxylic tetraimide and N,N',N",N"'-tetrakis(2,6-diisopropylphenyl)-diselenobiperylene-3,4,6,7 : 12,13,15,16-octacarboxylic acid tetraimide)

[0058]

[0059] Concrete synthetic steps are:

[0060] 1. Add 1mmol of N,N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetrachloroperylene-3,4:9,10-tetracarboxylic diimide , 12mmol sodium selenide, 6mmol cuprous iodide, 7mmol L-proline and 14mmol anhydrous potassium carbonate are mixed together;

[0061] 2. Add 10ml dimethyl sulfoxide to the mixture prepared in step 1;

[0062]3. Under nitrogen protect...

Embodiment 3

[0064] Example 3 (N, N', N", N"'-tetrakis(2,6-diisopropylphenyl)-thiabiperylene-3,4,6,7:12,13,15, 16-Octacarboxylic tetraimide and N,N',N",N"'-tetrakis(2,6-diisopropylphenyl)-dithiabiperylene-3,4,6,7 : 12,13,15,16-octacarboxylic acid tetraimide)

[0065]

[0066] Concrete synthetic steps are:

[0067] 1. Add 1 mmol N, N'-bis(2,6-diisopropylphenyl)-1,6,7,12-tetrabromoperylene-3,4:9,10-tetracarboxylic diimide , 14mmol sodium sulfide, 7mmol cuprous chloride, 8mmol L-proline and 11mmol anhydrous potassium carbonate are mixed together;

[0068] 2. Add 12ml dimethyl sulfoxide to the mixture prepared in step 1;

[0069] 3. Under nitrogen protection, heat the mixed solution prepared in step 2 to 80°C and react for 10 hours; after the reaction, the product is dissolved in ethyl acetate, washed with aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered, The solvent was evaporated to dryness below 60°C, and the product N, N', N", N"'-tetrakis(2,6-diisopropylphenyl...

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Abstract

The invention relates to a bridged dipyrene-3,4,6,7-12, 13, 15, 16-octcarboxylic acid tetraimide compound containing sulphur atoms or selenium atoms and a preparation method thereof. 1,6, 7,12-tetrahalogenated pyrene-3,4-9,10-tetracarboxylic acid diimide compound or 1,9,10,18-tetrahalogenated dipyrene-3,4,6,7-12, 13, 15, 16-octcarboxylic acid tetraimide compound, sodium sulfide or sodium selenide, a catalyst, an amino acid ligand and inorganic base are mixed; then an organic solvent is added; the reaction is carried out under the protection of inert gas; the product is dissolved in the solvent, is washed in sodium chloride aqueous solution, and is dried and filtrated; then the solvent is distilled to dryness; and the bridged dipyrene-3,4,6,7-12, 13, 15, 16-octcarboxylic acid tetraimide compound containing sulphur atoms or selenium atoms in the lateral position showed by formula(I) or (II) is obtained through column chromatography separation. The yield after purification is 10 to 40 percent.

Description

technical field [0001] The invention relates to a diperylene-3,4,6,7:12,13,15,16-octacarboxylic acid tetraimide compound containing a sulfur atom or a selenium atom bridging at the side position and a preparation method thereof. Background technique [0002] Perylene-3,4:9,10-tetracarboxylic acid diimide is an important industrial dye, because this kind of compound has good light stability, thermal stability and chemical inertness, and high Tinting power from red to purple (Chem. Commun., 2004, 1564-1579; Heterocycles, 1995, 40, 477-500). In addition to being used as a dye, perylene-3,4:9,10-tetracarboxylic diimide has also been widely used in functional materials, such as solar cell materials, liquid crystal materials, organic field effect tubes, luminescent materials, etc. ( Science, 2001, 293, 1119~1122; J.Am.Chem.Soc., 2006, 128, 3870~3871; J.Am.Chem.Soc., 2003, 125, 8625~8638; J.Am.Chem. Soc., 2003, 125, 437~443; Angew.Chem.Int.Ed., 2004, 43, 6363~6366; Angew.Chem.Int...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22C07D517/22
Inventor 王朝晖钱华磊
Owner INST OF CHEM CHINESE ACAD OF SCI
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