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Method for synthesizing metal-tetracyano-p-benzoquinone dimethane ester derivative

A technology of benzoquinodimethane and a synthesis method is applied in the synthesis field of metal-tetracyano-p-benzoquinodimethane lipid derivatives, and can solve the problems of difficult spin-coating molding, low solubility, hindering the application of compounds and the like, and achieves The effect of easy control of reaction conditions and high yield

Inactive Publication Date: 2003-12-10
SHANGHAI INST OF OPTICS & FINE MECHANICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, metal-tetracyanoquinone dimethane electron transfer complex has extremely low solubility in commonly used organic solvents, and is only slightly soluble in a few non-usable solvents such as acetonitrile, (such as copper-tetracyanoquinone dimethane ester The solubility of the electron transfer complex of derivatives in acetonitrile is: 0.03mg / ml), it is difficult to adopt the easy-to-practice and low-cost spin-coating method to form, thus greatly hindering the application of this compound in the above-mentioned fields

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Concrete synthetic steps are as follows:

[0022] Weigh raw materials according to the following weight percentage:

[0023] TCNQ lipid derivatives are selected from 2,5-dipropionic acid methyl ester-7,7,8,8-tetracyanoquinone dimethane: (TCNQ(CH 2 CH 2 COOCH 3 ) 2 ): 0.5%

[0024] NaI: 0.5%

[0025] CuI: 0.5%

[0026] Acetonitrile: 98.5%

[0027] At 85°C, dissolve methyl 2,5-dipropionate-7,7,8,8-tetracyanoquinodimethane in acetonitrile, and pass nitrogen protection;

[0028] Add NaI, stir to make NaI fully dissolve, add cuprous iodide (CuI), and react for 2 hours;

[0029] After the reaction is complete, the resulting crude product is filtered out, purified, and dried to obtain 2,5-dipropylmethyl ester-7,7,8,8-tetracyanoquinone dimethane lipid derivative electron transfer Complex: Cu(TCNQ(CH 2 CH 2 COOCH 3 ) 2 )

[0030] Yield: 89%, melting point: 278°C.

[0031] The characteristic absorption peak of infrared spectrum is: 2960cm -1 , 2193cm -1 , 173...

Embodiment 2

[0034] Weigh the synthetic raw materials in the following percentages by weight:

[0035] TCNQ lipid derivatives are selected from 2,5-dipropionic acid methyl ester-7,7,8,8-tetracyanoquinone dimethane: (TCNQ(CH 2 CH 2 COOCH 3 ) 2 ): 0.6%

[0036] AgI: 0.6%

[0037] NaI: 0.6%

[0038] Acetonitrile: 98.2%

[0039] At 70°C, dissolve methyl 2,5-dipropionate-7,7,8,8-tetracyanoquinodimethane in acetonitrile, and pass through nitrogen protection;

[0040] Add NaI, stir to make NaI fully dissolve, add silver iodide (AgI), and react for 1.5 hours;

[0041] After the reaction is complete, the resulting crude product is filtered out, purified, and dried to obtain 2,5-dipropylmethyl ester-7,7,8,8-tetracyanoquinone dimethane lipid derivative electron transfer Complex: Ag(TCNQ(CH 2 CH 2 COOCH 3 ) 2 )

[0042] Yield: 88%. The melting point is 278°C.

[0043] The characteristic absorption peak of infrared spectrum is: 2960cm -1 , 2193cm -1 , 1735cm -1 , 1637cm -1 , 1512...

Embodiment 3

[0046] Concrete synthetic steps are as follows:

[0047] Weigh the synthetic raw materials in the following percentages by weight:

[0048] TCNQ lipid derivatives are selected from 2,5-ethyl dipropionate-7,7,8,8-tetracyanoquinone dimethane: (TCNQ(CH 2 CH 2 COOCH2 CH 3 ) 2 ):2%

[0049] CuI: 2%

[0050] NaI: 2%

[0051] Acetonitrile: 94%

[0052] Dissolve ethyl 2,5-dipropionate-7,7,8,8-tetracyanoquinodimethane in acetonitrile at 70°C, and pass through nitrogen protection;

[0053] Add NaI, stir to make NaI fully dissolve, add cuprous iodide (CuI), and react for 1.5 hours;

[0054] After the reaction is complete, the resulting crude product is filtered out, purified, and dried to obtain 2,5-dipropylmethyl ester-7,7,8,8-tetracyanoquinone dimethane lipid derivative electron transfer Complex: Cu(TCNQ(CH 2 CH 2 COOCH 2 CH 3 ) 2 ).

[0055] Yield: 89%, melting point: 250°C.

[0056] The characteristic absorption peak of the infrared spectrum is: 2955cm -1 , 2193c...

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Abstract

The method for synthesizing metal-tetracyano-p-benzoquinodimethane lipoid derivative includes the following steps: placing the compound containing required metal ion into the acetonitrile solution in the which the TCNQ lipoid derivative and NAI are dissolved, stirring them at the normal temp.-85 deg.C and reacting for 1-2 hr. so as to obtain the invented product. Said invention also provides its reaction formula.

Description

Technical field: [0001] The present invention is related to electron transfer complexes, in particular to a method for synthesizing metal-tetracyanoquinone dimethane lipid derivatives, specifically about 2,5-dipropionic acid-7,7,8 , The synthesis method of the metal-based electron transfer complex of 8-tetracyanoquinone dimethane lipid derivatives. Background technique: [0002] Due to the wide application of microelectronic devices and nanoelectronic devices, the research on organic macromolecules and polymers in microelectronic devices and nanoelectronic devices is receiving increasing attention. Carbon-containing organic, organic-metallic composites, organic-semiconductor composites and pure organic-organic composites are characterized by small size, light weight, variable composition, easy cutting and assembly, low cost, and ultra-fast response speed. , making it possible to replace traditional inorganic materials, thereby realizing a revolution in electronics and compu...

Claims

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Application Information

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IPC IPC(8): C07C255/31C07F1/08
Inventor 黄伍桥吴谊群顾冬红干福熹
Owner SHANGHAI INST OF OPTICS & FINE MECHANICS CHINESE ACAD OF SCI
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