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Method for preparing carbon nanoring and cyclic compound suitable for use as raw material thereof

一种环状化合物、碳纳米环的技术，应用在有机化合物的制备、碳化合物催化剂、从含氧有机化合物制烃等方向

Inactive Publication Date: 2016-04-27
NAGOYA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Method for preparing carbon nanoring and cyclic compound suitable for use as raw material thereof
  • Method for preparing carbon nanoring and cyclic compound suitable for use as raw material thereof
  • Method for preparing carbon nanoring and cyclic compound suitable for use as raw material thereof

Examples

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preparation example Construction

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

[0117] The production method of the cyclic compound (1) of the present invention comprises a step (I): forming the compound (1) using the compound (3) in the presence of a nickel compound.

[0118] In this step (I), a plurality of compounds (3) of the same type are bonded (self-coupling) to form a cyclic compound (Z). The bonding between multiple and similar compounds (3) in the step (I) is a well-known bonding reaction called Yamamoto coupling. The compound (3) has two halogen atoms, and 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 a carbon atom bonded to a halogen atom in another compound (3). Accordingly, the coupling reaction between the compounds (3) can be continuously carried out, and the carbon atoms can be bonded to each other to obtain the cyclic compound (1).

[0119...

Embodiment

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

[0327] In this example, carbon nanorings composed of cycloparaphenylene were prepared. First, after preparing cis-1,4-bis(4-iodophenyl)-1,4-cyclohexanediol (Synthesis Example 1~3), 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, carbon nanorings were prepared using this cis-1,4-bis(4-iodophenyl)-1,4-bis(methoxymethyl ether)cyclohexane (Examples 1 to 3). Furthermore, the cycloparaphenylene compounds obtained in Examples 1 to 3 were crystallized and analyzed for their structures. In addition, in Examples 4 to 5, a cyclo-paraphenylene com...

Synthetic example 1

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

[0329] Add 1,4-diiodobenzene (49.5 g, 150 mmol) and anhydrous tetrahydrofuran (300 cm 3 ), after the solution was obtained, it was cooled to -78°C. Then, slowly add to this 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, 1,4-cyclohexadiene (5.68 g, 50 mmol) in anhydrous tetrahydrofuran (160 cm 3 ) solution, reacted at -78°C for 1 hour, and further reacted at room temperature (25°C) for 2 hours. After the reaction, distilled water (100 cm 3 ) and ethyl acetate (500cm 3 ), and put the mixture into a separatory funnel. By the extraction operation using this separatory funnel, two layers consisting of an ethyl acetate layer (i) and a water layer were separated. After recovering the ethyl acetate l...

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Abstract

In the present invention, in the presence of a nickel compound (bis(1,5-cyclooctadiene)nickel, etc.), a compound containing at least one cyclohexane ring portion with benzene rings to which halogen atoms are attached at both ends is used , a cyclic compound (1) in which organic ring groups including a cyclohexane ring and a benzene ring are continuously bonded can be formed. Then, the desired carbon nanoring can be obtained by converting the cyclohexane ring part of the cyclic compound (1) into a benzene ring part. According to this, a carbon nanoring composed of a cyclic structure compound in which a desired number of organic ring groups are continuously bonded can be efficiently produced in a short process.

Description

technical field [0001] The invention relates to a method for preparing a carbon nanoring and a method for preparing a cyclic compound suitable as a raw material for the preparation of the carbon nanoring. made. [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, pyridyl, pyrimidyl, etc. A divalent heterocyclic group, or a derivative group in which a hydrogen atom bonded to a carbon atom constituting these groups is substituted with a functional group. Background technique [0003] Conventionally, carbon nanotubes having a cylindrical structure in which two-dimensional graphene sheets are rolled, ring-shaped carbon nanotubes composed of the carbon nanotubes, and the like are known as nanostructures containing carbon atoms. [0004] Carbon nanotubes are extremely mechanically strong, resi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C1/20C07C15/14C07B61/00
CPCC07C41/30C07C43/188C07C43/192C07B37/04C07C1/24C07C2521/06C07C2523/14C07C2523/28C07C2523/30C07C2527/054C07C2527/055C07C2527/10C07C2527/19C07C2527/199C07C2531/025C07C2531/14C07C2601/14C07C13/28
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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