Heterocyclic fused imidazolone, dioxolone, imidazolethione and dioxolethione monomers

A technology of monomers and compounds, applied in the field of monomers for generating conductive polymers, can solve the problems of dangerous storage and disposal, difficult operation, etc.

Inactive Publication Date: 2007-12-05
AIR PROD & CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, known monomer generation methods, especially those disclosed in US 2,487,051 and the Mozingo paper, utilize toxic chemicals including phosgene in the preparation of various monomers, which results in difficult handling, storage and disposal. Hazardous Reactive Chemicals

Method used

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  • Heterocyclic fused imidazolone, dioxolone, imidazolethione and dioxolethione monomers
  • Heterocyclic fused imidazolone, dioxolone, imidazolethione and dioxolethione monomers
  • Heterocyclic fused imidazolone, dioxolone, imidazolethione and dioxolethione monomers

Examples

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preparation example Construction

[0056] The method of the present invention can include the synthesis of 1H-thieno[3,4-d]imidazolin-2(3H)-one in a single reaction mixture. The synthesis method of 1H-thieno[3,4-d]imidazolin-2(3H)-one according to the present invention includes the mechanism shown below:

[0057] This first reactant compound, second reactant compound, solvent and base are present in the reaction mixture. In the above reaction, 3,4-diaminothiophene dihydrochloride is shown as sodium carbonate (Na 2 CO 3 ) Reacts in the presence of a base to form 3,4-diaminothiophene, which reacts with the second reactant compound of urea shown above to form 1H-thieno[3,4-d]imidazoline-2(3H)- ketone.

[0058] The method of the present invention also includes the synthesis of imidazolinone selenophene derivatives. In this embodiment of the present invention, the reaction of 3,4-diaminoselenophene dihydrochloride is as follows:

[0059] In the above reaction, 3,4-diaminoselenophene dihydrochloride is shown as sod...

Embodiment 1

[0078] According to the method of the present invention, the compound 1H-thieno[3,4-d]imidazolin-2(3H)-one is prepared in a single reaction mixture. In Example 1, triethylamine was used as a base to release 3,4-diaminothiophene from dihydrochloride. Urea is used as the second reactant compound containing a carbonyl group.

[0079] Set the quantity to 0.1922g (1.028×10 -3 mol) 3,4-Diaminothiophene dihydrochloride ("DAT-HCl") and 0.1866g (3.11×10 -3 mol; 3.02 equivalents based on DAT-HCl) Urea was added to a 50 mL three-necked flask equipped with magnetic stirring and reflux condenser. The flask was purged with nitrogen for 15 minutes, after which 20 mL of 1,3-dimethyl-2-imidazolidinone ("DMI") was added with a syringe under stirring. Heat the contents to 50℃, at this time add 0.45mL (0.327g, 3.23×10 -3 mol; 3.14 equivalents based on DAT-HCl) triethylamine. The temperature of the flask was raised to 115-120°C and kept in this temperature range for 4 hours. After cooling and filte...

Embodiment 2

[0082] According to the method of the present invention, 1H-thieno[3,4-d]imidazolin-2(3H)-one is prepared in a single reaction mixture. Example 2 uses 4-(dimethylamino)pyridine, an alternative base of Example 1, as the base to release 3,4-diaminothiophene from the dihydrochloride. In addition, Example 2 uses 1,1'-carbonyldiimidazole as the second reactant compound.

[0083] Set the quantity to 0.1934g (1.034×10 -3 mol) 3,4-Diaminothiophene dihydrochloride (DAT-HCl), 0.4862g (3.001×10 -3 mol; 2.90 equivalents based on DAT-HCl) 1,1'-carbonyldiimidazole, and 0.3957g (3.243×10 -3 mol; 3.14 equivalents based on DAT-HCl) 4-(dimethylamino)pyridine was added to a 50 mL three-necked flask equipped with magnetic stirring and reflux condenser. The flask was purged with nitrogen for 15 minutes, and then 20 mL of 1,3-dimethyl-2-imidazolidinone (DMI) was added with a syringe while stirring. The temperature of the flask was raised to 115-120°C and kept in this temperature range for 4 hours. Afte...

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Abstract

A method of making a compound of the formula shown below is disclosed: wherein Z is Se or S; Y is NH or O; X is O or S and W and W' are independently selected from the group consisting of hydrogen, -C=ONH 2 , -C=ONHR', -C=ONR'R', -C N, and R' is C 1-6 alkyl and the resultant monomer compounds. The method includes contacting a 3,4-disubstituted thiophene or selenophene or disubstituted thiophene or selenophene derivatives with a carbonyl or thiocarbonyl containing compound selected from the group consisting of ureas, thioureas, carbonate esters, thionocarbonates, thiocarbonate esters, or orthocarbonates. The monomer compounds are suitable for forming polymers for use in a wide range of electronic applications.

Description

[0001] Cross reference of related patent applications [0001] The subject matter of this patent application relates to U.S. Patent Application No. 11 / 446,000 entitled "Conductive Polymer and Conductive Polymer Manufacturing Method" filed on the same day as this article, the publication of which is incorporated herein by reference. Technical field [0002] The present invention relates to a monomer for producing a conductive polymer and a method for producing the monomer. Background technique [0003] Conductive polymers have been developed as a material of choice for various organic optoelectronics applications. Such optoelectronic applications include polymer light-emitting diodes (thin film displays), solid-state lighting, organic photovoltaics, advanced storage devices, organic field effect transistors, supercapacitors, electroluminescent devices, printed electronics, conductors, lasers, and sensors . [0004] One of the first types of conductive polymers is polyacetylene, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C07D517/04
CPCC07D495/04C07D517/04
Inventor S·赞M·E·福特
Owner AIR PROD & CHEM INC
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