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Indolecarboxylic ester trimer and electrochemical cell using the same

An indole carboxylate, trimer technology, used in organic chemistry, battery electrodes, optics, etc.

Inactive Publication Date: 2005-08-31
TOKIN CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the aforementioned WO02 / 32903 does not specifically describe indole carboxylate trimers in terms of process examples

Method used

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  • Indolecarboxylic ester trimer and electrochemical cell using the same
  • Indolecarboxylic ester trimer and electrochemical cell using the same
  • Indolecarboxylic ester trimer and electrochemical cell using the same

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0115] Preparation Example 1 (synthesis of methyl 4-dimethylaminovinyl-3-nitrobenzoate)

[0116] Add 89.7 g of 4-methyl-3-nitrobenzoic acid methyl ester, 82.1 g of dimethylformamide dimethyl acetal and 200 ml of dimethylformamide (DMF) in the reaction flask, The contents were stirred at 120 °C for 6 hours. DMF was distilled off to obtain a reddish-purple solid product. Then, 300 ml of methanol was poured into the flask to wash the crystalline material and filtered. 104.8 g (91% yield) of methyl 4-dimethylaminovinyl-3-nitrobenzoate are obtained.

preparation Embodiment 2

[0117] Preparation Example 2 (synthesis of indole-6-carboxylic acid methyl ester monomer-catalytic reduction method)

[0118] 87.1 g of methyl 4-methyl-3-nitrobenzoate, 400 ml of methanol and 8 g of 5% palladium-carbon (Pd / C) were added to the reaction flask. The contents of the flask were stirred at room temperature under a hydrogen atmosphere for 12 hours at atmospheric pressure. The Pd / C was removed by filtration and the methanol was distilled off from the filtrate to give the product as a yellowish solid. The product was dissolved in ethyl acetate, washed with 5% aqueous NaOH, washed with 5% aqueous hydrochloric acid and water, and the ethyl acetate was distilled off. Thus, 50.4 g (68.7% yield) of methyl indole-6-carboxylate monomer was obtained.

preparation Embodiment 3

[0119] Preparation Example 3 (synthesis of indole-6-methyl carboxylate monomer-iron powder reduction method)

[0120] 176.4 g of iron powder, 43.5 g of acetic acid, 71.2 g of water and 273.3 g of toluene were added to the reaction flask. The contents of the flask were heated to 80°C. Then, a solution of 131.8 g of methyl 4-methyl-3-nitrobenzoate in 110.4 g of DMF was added dropwise to the above-mentioned mixed solution during about 1 hour, and then the resulting mixture was stirred again at 80 degrees Celsius for 4 Hour. After cooling the reaction mixture, solid material was removed by filtration. The filtrate was washed with 5% aqueous NaOH, then 5% aqueous hydrochloric acid and water, after which the toluene was distilled off to give the product as a brown solid. Then, 164.3 g of cyclohexane was added to dissolve the solid product at about 80 degrees Celsius. The resulting solution was cooled to room temperature, and the precipitated crystalline substance was collected b...

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PUM

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Abstract

The present invention provides a novel indole carboxylic ester trimer which is characterized by being represented by the following general formula (1): wherein R represents a straight or branched chain alkyl group having 1-6 carbon atoms; n is an integer of 1-4; Xa- represents at least one anion selected from a group of anions having a valency of 1-3 consisting of chloride ion, bromide ion, iodide ion, fluoride ion, nitrate ion, sulfate ion, hydrogen sulfate ion, phosphate ion, borofluoride ion, perchlorate ion, thiocyanate ion, acetic acid ion, propionic acid ion, methanesulfonic acid ion, p-toluenesulfonic acid ion, trifluoroacetic acid ion and trifluoromethanesulfonic acid ion; a represents the ionic valence number of X and is an integer of 1-3; and m is 0-0.5.

Description

technical field [0001] The present invention relates to novel indole carboxylate trimers. A composition containing the trimer as a main component can be used as an electrochemical cell, a chemical sensor, an organic EL material for a display element, a nonlinear material, and the like. Background technique [0002] As trimerized indole derivatives, 6-nitroindole trimer and 5-cyanindole trimer have hitherto been known. These trimer derivatives have been used as electrochemical cells using protons as charge carriers (see Japanese Patent Laid-Open No. 2002-93419). On the other hand, WO02 / 32903 relates to indole carboxylic acid trimer derivatives, such as indole-4-carboxylic acid trimer, indole-5-carboxylic acid trimer, indole-6-carboxylic acid trimer polymer, indole-7-carboxylic acid trimer, etc. However, the aforementioned WO 02 / 32903 does not specifically describe indole carboxylate trimers in terms of process examples. [0003] As mentioned above, 6-nitroindole trimer, 5...

Claims

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Application Information

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IPC IPC(8): C07D487/14C07D519/00G02F1/03H01M4/60
CPCH01M4/60C07D487/14H01M4/608Y02E60/10
Inventor 大井英男谷泽尚人三谷胜哉信田知希西山利彦吉成哲也高桥直树
Owner TOKIN CORP
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