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Synthetic method of fullerene spiro derivative

A synthesis method, fullerene technology, applied in the direction of organic chemistry, can solve the problems of limited preparation methods, less fullerene and spiro ring structure, etc., and achieve the effects of environmental friendliness, wide application range of substrates, and simple production process

Active Publication Date: 2021-03-12
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among the many known fullerene derivatives, fullerenes have few spiro ring structures and limited preparation methods

Method used

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  • Synthetic method of fullerene spiro derivative
  • Synthetic method of fullerene spiro derivative
  • Synthetic method of fullerene spiro derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Preparation of Fullerenospiro Derivative 2a

[0015]

[0016] Reaction steps:

[0017] Take a dry 15mL Shrek tube, add fullerene C to it sequentially 60 (36.0mg, 0.05mmol), compound (0.1mmol), Pd(PPh 3 ) 4 (2.9mg, 0.0025mmol) and Cs 2 CO 3 (32.6mg, 0.1mmol), ultrasonically dissolved the solid in anhydrous CB (6mL), placed the reaction tube in an oil bath at 130°C for 24 hours, lifted the reaction tube to cool to room temperature after the reaction, and evaporated the solvent in vacuo The residue was separated on a silica gel column with CS 2 as eluent to recover unreacted fullerene C 60 , then use the volume ratio CS 2 / DCM=8:1 was used as the eluent to obtain the target product fullerene and spiro derivative 2a, and the isolated yield of product 2a was 48%.

[0018] Product 2a: 1 H NMR (400MHz, CDCl 3 / CS 2 )δ7.77(d, J=7.6Hz, 1H), 7.69(d, J=7.2Hz, 1H), 7.57–7.49(m, 2H), 7.37(d, J=7.6Hz, 1H), 7.23( t,J=8.0Hz,1H),6.91(t,J=8.0Hz,2H),6.63(d,J=9.2Hz,1H),5.0...

Embodiment 2

[0020] Preparation of fullerene and spiro derivative 2b

[0021]

[0022] Reaction steps:

[0023] Take a dry 15mL Shrek tube, add fullerene C to it sequentially 60 (36.0mg, 0.05mmol), compound (0.1mmol), Pd(PPh 3 ) 4 (2.9mg, 0.0025mmol) and Cs 2 CO 3 (32.6mg, 0.1mmol), ultrasonically dissolved the solid in anhydrous CB (6mL), placed the reaction tube in an oil bath at 130°C for 24 hours, lifted the reaction tube to cool to room temperature after the reaction, and evaporated the solvent in vacuo The residue was separated on a silica gel column with CS 2 as eluent to recover unreacted fullerene C 60 , then use the volume ratio CS 2 / DCM=8:1 was used as the eluent to obtain the target product fullerene and spiro derivative 2b, and the isolated yield of product 2b was 40%.

[0024] Product 2b: 1 H NMR (600MHz, CDCl 3 / CS 2 )δ7.83(d, J=7.8Hz, 1H), 7.69(d, J=7.2Hz, 1H), 7.56(t, J=7.8Hz, 1H), 7.53(t, J=7.8Hz, 1H) ,6.92(s,1H),6.81–6.78(m,2H),6.60(d,J=9.0Hz,1H),5.01(d...

Embodiment 3

[0026] Preparation of fullerene and spiro derivative 2c

[0027]

[0028] Reaction steps:

[0029] Take a dry 15mL Shrek tube, add fullerene C to it sequentially 60 (36.0mg, 0.05mmol), compound (0.1mmol), Pd(PPh 3 ) 4 (2.9mg, 0.0025mmol) and Cs 2 CO 3 (32.6mg, 0.1mmol), ultrasonically dissolved the solid in anhydrous CB (6mL), placed the reaction tube in an oil bath at 130°C for 24 hours, lifted the reaction tube to cool to room temperature after the reaction, and evaporated the solvent in vacuo The residue was separated on a silica gel column with CS 2 as eluent to recover unreacted fullerene C 60 , then use the volume ratio CS 2 / DCM=8:1 was used as the eluent to obtain the target product fullerene and spiro derivative 2c, and the isolated yield of product 2c was 45%.

[0030] Product 2c: 1 H NMR (600MHz, CDCl 3 / CS 2 )δ7.72(d, J=7.2Hz, 1H), 7.68(d, J=6.6Hz, 1H), 7.58–7.53(m, 2H), 7.44(s, 1H), 7.31(d, J=8.4 Hz,1H),6.78(d,J=8.4Hz,1H),6.63(d,J=9.6Hz,1H),5.04(d...

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Abstract

The invention discloses a synthetic method of a fullerene spiro derivative, and belongs to the technical field of synthesis of fullerene derivatives. According to the technical scheme, the preparationmethod is characterized by comprising the steps of by taking a terminal alkenyl-containing compound of o-iodophenol / o-iodoaniline as a reaction raw material, reacting with fullerene C60 at the temperature of 130-150 DEG C under the catalysis of palladium salt Pd(PPh3)4 and the promotion of cesium salt Cs2CO3 to form three C-C bonds and construct two rings at the same time in a series process of Heck / C-H activation, and directly synthesizing the fullerene spiro derivative with diversified structures by a one-pot method. The method is simple in production process, environmentally friendly, widein substrate application range and high in yield; and the domino strategy of transition metal catalysis used in the production process is not only suitable for synthesis of a spiro structure, but also suitable for synthesis of other complex fullerene derivative structures.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fullerene derivatives, in particular to a synthesis method of fullerene and spiro derivatives. Background technique [0002] Fullerene C 60 It has a three-dimensional large π electron system, so it has good electron-accepting properties and high electron mobility, and is a good n-type semiconductor material. Fullerene derivatives are a class of carbon nanomolecules with extensive and important applications in the fields of photoelectric transfer materials and solar cell acceptor materials. Since the structure is closely related to the photoelectric properties, it is of great significance to develop new methods to construct fullerene derivatives with diverse structural features. Among the many known fullerene derivatives, fullerene has few spiro ring structures and limited preparation methods. Therefore, the development of new methods to prepare fullerene spiro derivatives is an urgent prob...

Claims

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Application Information

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IPC IPC(8): C07D307/94
CPCC07D307/94Y02E10/549
Inventor 刘统信张朋玲马金亮张贵生
Owner HENAN NORMAL UNIV
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