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

A technology of benzoquinodimethane and its synthesis method, which is applied in the field of synthesis of metal-tetracyano-p-benzoquinone dimethane ester derivatives, can solve problems such as low solubility, difficult spin coating molding, hindering the application of compounds, etc., and achieves The effect of high yield and easy control of reaction conditions

Inactive Publication Date: 2005-06-15
SHANGHAI INST OF OPTICS & FINE MECHANICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the metal-tetracyanoquinone dimethane electron transfer complex has extremely low solubility in commonly used organic solvents, and is only slightly soluble in a few non-used solvents such as acetonitrile, (such as copper-tetracyanoquinone dimethane 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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  • Method of synthesizing metal-tetracyano-p-benzoquinone dimethane ester derivative
  • Method of synthesizing metal-tetracyano-p-benzoquinone dimethane ester derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Concrete synthetic steps are as follows:

[0024] Weigh raw materials according to the following weight percentage:

[0025] TCNQ ester derivatives choose 2,5-dipropionate methyl ester-7,7,8,8-tetracyanoquinone dimethane:

[0026] (TCNQ(CH 2 CH 2 COOCH 3 ) 2 ): 0.5%

[0027] NaI: 0.5%

[0028] CuI: 0.5%

[0029] Acetonitrile: 98.5%

[0030] At 85°C, dissolve methyl 2,5-dipropionate-7,7,8,8-tetracyanoquinodimethane in acetonitrile, and pass nitrogen protection;

[0031] Add NaI, stir to make NaI fully dissolve, add cuprous iodide (CuI), and react for 2 hours;

[0032] After the reaction is complete, the resulting crude product is filtered out, purified, and dried to obtain copper 2,5-dipropionate methyl ester-7,7,8,8-tetracyanoquinone dimethane derivatives Electron transfer complex:

[0033] Cu(TCNQ(CH 2 CH 2 COOCH 3 ) 2 )

[0034] Yield: 89%, melting point: 278°C.

[0035] The characteristic absorption peak of infrared spectrum is: 2960cm -1 , 2193...

Embodiment 2

[0038] Weigh the synthetic raw materials in the following percentages by weight:

[0039] TCNQ ester derivatives choose 2,5-dipropionate methyl ester-7,7,8,8-tetracyanoquinone dimethane:

[0040] (TCNQ(CH 2 CH 2 COOCH 3 ) 2 ): 0.6%

[0041] AgI: 0.6%

[0042] NaI: 0.6%

[0043] Acetonitrile: 98.2%

[0044] At 70°C, dissolve methyl 2,5-dipropionate-7,7,8,8-tetracyanoquinodimethane in acetonitrile, and pass through nitrogen protection;

[0045] Add NaI, stir to make NaI fully dissolve, add silver iodide (AgI), and react for 1.5 hours;

[0046] After the reaction is complete, the resulting crude product is filtered out, purified, and dried to obtain silver 2,5-dipropionate methyl ester-7,7,8,8-tetracyanoquinone dimethane derivatives Electron transfer complex:

[0047] Ag(TCNQ(CH 2 CH 2 COOCH 3 ) 2 )

[0048] Yield: 88%. The melting point is 278°C.

[0049] The characteristic absorption peak of infrared spectrum is: 2960cm -1 , 2193cm -1 , 1735cm -1 , 1637c...

Embodiment 3

[0052] Concrete synthetic steps are as follows:

[0053] Weigh the synthetic raw materials in the following percentages by weight:

[0054] TCNQ ester derivatives choose 2,5-ethyl dipropionate-7,7,8,8-tetracyanoquinone dimethane:

[0055] (TCNQ(CH 2 CH 2 COOCH 2 CH 3 ) 2 ):2%

[0056] CuI: 2%

[0057] NaI: 2%

[0058] Acetonitrile: 94%

[0059] Dissolve ethyl 2,5-dipropionate-7,7,8,8-tetracyanoquinodimethane in acetonitrile at 70°C, and pass through nitrogen protection;

[0060] Add NaI, stir to make NaI fully dissolve, add cuprous iodide (CuI), and react for 1.5 hours;

[0061] After the reaction is complete, the resulting crude product is filtered out, purified, and dried to obtain copper 2,5-dipropionate-7,7,8,8-tetracyanoquinone dimethane derivatives Electron transfer complex:

[0062] Cu(TCNQ(CH 2 CH 2 COOCH 2 CH 3 ) 2 ).

[0063] Yield: 89%, melting point: 250°C.

[0064] The characteristic absorption peak of the infrared spectrum is: 2955cm -1 , 21...

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Abstract

A method for synthesizing metal-tetracyano-p-benzoquinodimethane ester derivatives, which is to put a compound containing a desired metal ion into an acetonitrile solution in which TCNQ ester derivatives and NaI (sodium iodide) are dissolved In the temperature range from room temperature to 85 °C, the electron transfer complex metal-tetracyano-p-benzoquinodimethane ester derivative can be obtained by stirring and reacting for one to two hours. The reaction formula is as follows: 2M + +3NaI+2TCNQ(CH 2 CH 2 COOR) 2 →2M(TCNQ(CH 2 CH 2 COOR) 2 )+3Na + +I 3 - C and N in the structural formula represent carbon and nitrogen, respectively, ROOCH 2 CH 2 R in - stands for alkyl: -C n H 2n+1 , n=1~10, M represents metal, Na represents sodium, and I represents iodine.

Description

technical field [0001] The present invention is related to electron transfer complexes, in particular to a method for synthesizing metal-tetracyanoquinone dimethane ester derivatives, specifically about 2,5-dipropionic acid-7,7,8 , The synthesis method of the metal-based electron transfer complex of 8-tetracyanoquinone dimethane ester 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 compute...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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