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Carbon nanoring and method for producing a ring-shaped compound suitable as a starting material for production of the same

A technology of cyclic compounds and carbon nanorings, which is applied in the preparation of organic compounds, carbon compound catalysts, and the production of hydrocarbons from oxygen-containing organic compounds, etc.

Inactive Publication Date: 2012-12-12
NAGOYA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in these preparation methods, there is a defect that carbon nanotubes of various thicknesses and lengths can only be obtained in the form of mixtures.

Method used

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  • Carbon nanoring and method for producing a ring-shaped compound suitable as a starting material for production of the same
  • Carbon nanoring and method for producing a ring-shaped compound suitable as a starting material for production of the same
  • Carbon nanoring and method for producing a ring-shaped compound suitable as a starting material for production of the same

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0116] [1] Preparation method of cyclic compound (1)

[0117] The method for preparing the cyclic compound (1) of the present invention has the step (I): in the presence of a nickel compound, the compound (3) is used to form the compound (1).

[0118] In this step (I), multiple and similar compounds (3) are bonded (self-coupling) to form a cyclic compound (Z). The bonding of multiple and similar compounds (3) in this step (I) is a known bonding reaction called Yamamoto coupling. The compound (3) has two halogen atoms. By using a nickel compound, the carbon atoms bonded to the halogen atoms can be bonded to each other, that is, the carbon atoms bonded to the halogen atoms in a compound (3), It is bonded to the carbon atom bonded to the halogen atom in the other compound (3). According to this, the coupling reaction between the compounds (3) can be continuously performed to bond the carbon atoms to each other to obtain the cyclic compound (1).

[0119] Compound (3) is a compound rep...

Embodiment

[0326] Hereinafter, the present invention will be specifically described with examples, but the present invention is not restricted by these examples. In addition, in the synthesis examples and the examples, the NMR measurement was performed with a nuclear magnetic resonance device (A-400) (model name) manufactured by JEOL.

[0327] In this example, a carbon nanoring composed of p-phenylene ring was prepared. First, after preparing cis-1,4-bis(4-iodophenyl)-1,4-cyclohexanediol (Synthesis Examples 1 to 3), use the cis-1,4-bis(4-iodophenyl) )-1,4-cyclohexanediol to prepare cis-1,4-bis(4-iodophenyl)-1,4-bis(methoxymethyl ether)cyclohexane (Synthesis Example 4). Next, the cis-1,4-bis(4-iodophenyl)-1,4-bis(methoxymethyl ether) cyclohexane was used to prepare carbon nanorings (Examples 1 to 3). In addition, the cyclic p-phenylene compounds obtained in Examples 1 to 3 were crystallized, and the structure was analyzed. In addition, in Examples 4 to 5, a paraphenylene compound composed...

Synthetic example 1

[0328] Synthesis Example 1: cis-1,4-bis(4-iodophenyl)-1,4-cyclohexanediol (compound (3a-1a)) Synthesis (Part One)

[0329] At room temperature (25℃), add 1,4-diiodobenzene (49.5g, 150mmol) and anhydrous tetrahydrofuran (300cm 3 ), after obtaining the solution, cool to -78°C. Then, slowly add to the solution (adding speed 3cm 3 / Min) hexane solution of n-butyllithium (93.8cm 3 , 1.6M, 150mmol). After the addition, keep the temperature (-78°C) and stir for 1 hour. Then, while stirring the reaction solution, add 1,4-cyclohexadiene (5.68g, 50mmol) in anhydrous tetrahydrofuran (160cm) separately prepared in an argon atmosphere 3 ) The solution was reacted at -78°C for 1 hour, and then at room temperature (25°C) for 2 hours. After the reaction, add distilled water (100cm 3 ) And ethyl acetate (500cm 3 ), put the mixture into a separatory funnel. By the extraction operation using this separatory funnel, it was separated into two layers consisting of an ethyl acetate layer (i) and an ...

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Abstract

Disclosed is a method capable of forming a ring-shaped compound (1) using a compound that contains at least one cyclohexane ring part and has on each end a benzene ring part that has a halogen atom in the presence of a nickel compound (bis(1,5-cyclooctadiene)nickel or the like) and wherein organic ring groups that contain a cyclohexane ring, benzene ring and the like are bonded continuously. If, thereafter, the cyclohexane ring part of the ring-shaped compound (1) is converted to a benzene ring part, a desired carbon nanoring may be obtained. By this means, a carbon nanoring formed from a ring-shaped compound in which a desired number of organic ring groups are bonded continuously may be produced efficiently with a small number of steps.

Description

Technical field [0001] The invention relates to a method for preparing a carbon nano ring and a method for preparing a cyclic compound suitable for use as a raw material for the preparation of the carbon nano ring. The carbon nano ring is formed by bonding a divalent aromatic hydrocarbon group and other organic ring groups to form a ring Become. [0002] In addition, in this specification, the "organic ring group" constituting the carbon nanoring means divalent aromatic hydrocarbon groups such as phenylene and naphthylene, divalent alicyclic hydrocarbon groups such as cyclohexylene, pyridine subunits, pyrimidine subunits, etc. A divalent heterocyclic group or a derivative group in which the hydrogen atom bonded to the carbon atom constituting these groups is replaced by a functional group. Background technique [0003] Currently, as nanostructures containing carbon atoms, carbon nanotubes having a two-dimensional graphene sheet rolled into a cylindrical structure, cyclic carbon na...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C1/20C07C15/14C07B61/00
CPCC07C43/188C07C2523/28C07B37/04C07C41/30C07C2523/14C07C2527/054C07C43/192C07C2531/025C07C1/24C07C2531/14C07C2101/14C07C2527/055C07C2523/30C07C2527/19C07C2527/199C07C2527/10C07C2521/06C07C2601/14C07C13/28
Inventor 伊丹健一郎濑川泰知宫本慎平大町辽松浦沙奈枝彼得·塞纳尔
Owner NAGOYA UNIVERSITY
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