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A kind of n-phenyl fullerene pyrrolidine derivative and its preparation method and application

A technology of phenylfullerene pyrrolidine and derivatives, which is applied in the field of material chemistry, can solve the problem of high separation work requirements, and achieve good light absorption characteristics, high open circuit voltage, and good photoelectric performance.

Inactive Publication Date: 2016-07-20
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, since the product added on the 5,6 bond will be produced during the synthesis process, and the polarity of the two products is similar, so the requirements for subsequent separation work are also relatively high

Method used

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  • A kind of n-phenyl fullerene pyrrolidine derivative and its preparation method and application
  • A kind of n-phenyl fullerene pyrrolidine derivative and its preparation method and application
  • A kind of n-phenyl fullerene pyrrolidine derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Preparation of N-phenyl-2-(2-methoxy)phenyl-3,4-fullerene pyrrolidine (FP1).

[0035]

[0036] Under the protection of Ar, add 100mg (0.14mmol) fullerene C60 to 50ml anhydrous toluene solution, ultrasonically obtain the toluene solution of fullerene, then add 85mg (0.56mmol) N-phenylglycine and 38mg (0.28mmol) 2-Methoxybenzaldehyde was stirred and heated to 115°C, refluxed for 6 hours, and cooled to room temperature to obtain a reaction liquid.

[0037] The reaction solution was distilled under reduced pressure, and crudely separated by silica gel column chromatography: firstly, the unreacted fullerene C60 was separated and removed by a mixed solvent of n-hexane / toluene with a volume ratio of 10:1, and then the unreacted fullerene C60 was used with a volume ratio of 2:1 The crude product of N-phenyl-2-(2-methoxy)phenyl-3,4-fullerene pyrrolidine was separated by n-hexane / toluene mixed solvent.

[0038]The crude product was purified by HPLC (chromatographic...

Embodiment 2

[0040] Example 2: Preparation of N-phenyl-2-(2-hexyloxy)phenyl-3,4-fullerenylpyrrolidine (FP2).

[0041]

[0042] Under the protection of Ar, add 100mg (0.14mmol) fullerene C60 to 50ml anhydrous toluene solution, ultrasonically obtain the toluene solution of fullerene, then add 85mg (0.56mmol) N-phenylglycine and 59mg (0.28mmol) 2-Hexyloxybenzaldehyde was stirred and heated to 115°C, refluxed for 9 hours, and cooled to room temperature to obtain a reaction liquid.

[0043] The reaction liquid was distilled under reduced pressure, and crude separation was carried out by silica gel column chromatography: firstly, the unreacted fullerene C60 was separated and removed by a mixed solvent of n-hexane / toluene with a volume ratio of 10:1, and then the unreacted fullerene C60 was used with a volume ratio of 3:1 The crude product of N-phenyl-2-(2-hexyloxy)phenyl-3,4-fullerene pyrrolidine was separated by n-hexane / toluene mixed solvent.

[0044] The crude product was purified by HPLC...

Embodiment 3

[0046] Example 3: Preparation of N-phenyl-2-[2-(2-ethylhexyloxy)]phenyl-3,4-fullerene pyrrolidine (FP3).

[0047]

[0048] Under the protection of Ar, add 100mg (0.14mmol) fullerene C60 to 50ml anhydrous toluene solution, ultrasonically obtain the toluene solution of fullerene, then add 85mg (0.56mmol) N-phenylglycine and 66mg (0.28mmol) 2-Ethylhexyloxybenzaldehyde was stirred and heated to 115°C, refluxed for 12 hours, and cooled to room temperature to obtain a reaction liquid.

[0049] The reaction liquid was distilled under reduced pressure, and crude separation was carried out by silica gel column chromatography: firstly, the unreacted fullerene C60 was separated and removed by a mixed solvent of n-hexane / toluene with a volume ratio of 10:1, and then the unreacted fullerene C60 was used with a volume ratio of 3:1 The crude product of N-phenyl-2-[2-(2-ethylhexyloxy)]phenyl-3,4-fullerene pyrrolidine was obtained by separation with n-hexane / toluene mixed solvent.

[0050]...

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Abstract

The invention discloses an N-phenylfullerene pyrrolidine derivative, a preparation method and application thereof. Specifically, the present invention provides a N-phenylfullerene pyrrolidine derivative as shown in formula (I), wherein: R 1 for C 1 -C 10 straight-chain or branched-chain alkoxy, C 2 -C 10 straight-chain or branched alkenyloxy, C 2 -C 10 straight-chain or branched alkynyloxy, phenoxy or naphthyloxy; R 2 for hydrogen, C 1 -C 10 straight-chain or branched-chain alkoxy, C 2 -C 10 straight-chain or branched alkenyloxy, C 2 -C 10 straight-chain or branched alkynyloxy, phenoxy or naphthyloxy. The derivative can be prepared by the addition and ring closure reaction of fullerene C60, N-phenylglycine and substituted benzaldehyde with a molar ratio of 1:3~4:1.5~2 under the protection of an inert gas , and then used as an electron acceptor material that can replace PCBM for the preparation of photovoltaic devices such as solar cells.

Description

technical field [0001] The invention belongs to the field of material chemistry, and relates to a fullerene pyrrolidine derivative, in particular to an N-phenylfullerene pyrrolidine derivative, its preparation method, and its use as an acceptor material in the preparation of photovoltaic devices use. Background technique [0002] Fullerene C60 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. In addition, fullerenes have the characteristics of electron-deficient olefins and are prone to addition reactions, so various fullerene derivatives can be prepared through addition reactions. The electrical properties, optical properties, solubility and compatibility with other materials of fullerene can be further adjusted by selecting the addition type and addition group. In recent years, fullerenes and their derivatives have been widely used in organic optoelectroni...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/96H01L51/42H01L51/46
CPCC07D209/96H10K85/215H10K30/00Y02E10/549Y02P70/50
Inventor 冯莱周祎梁雨岚刘晓东郝亚娟
Owner SUZHOU UNIV