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Perylene monoimide peri-fused fullerene derivatives and its preparation method and application

A technology of fullerenes and compounds, applied in the field of organic chemical synthesis, can solve problems such as weak absorption

Active Publication Date: 2020-09-29
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

PCBM-like electron acceptor materials have many advantages, such as good solubility, high electron mobility, and good phase separation with common polymer donors, etc. However, PCBM-like materials have weak absorption in the visible light region.

Method used

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  • Perylene monoimide peri-fused fullerene derivatives and its preparation method and application
  • Perylene monoimide peri-fused fullerene derivatives and its preparation method and application
  • Perylene monoimide peri-fused fullerene derivatives and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] The preparation of embodiment 1 formula (I-1) compound

[0102] Under nitrogen protection, 9-bromoperylene monoimide (154mg, 0.278mmol), fullerene C60 (200mg, 0.278mmol), palladium acetate, (4mg, 0.017mmol), tricyclohexylphosphine tetrafluoroborate (13mg, 0.034mmol), anhydrous potassium carbonate (153mg, 1.112mmol) and 8mL 1-methylnaphthalene, heated to 200°C, reacted for 3h, cooled After reaching room temperature, the reaction solution was poured into methanol, and the precipitate was collected by suction filtration, washed with methanol, dried, and purified on a silica gel column, using carbon disulfide as a developing solvent to obtain 159 mg of the compound of formula (I-1), with a yield of 48%.

[0103]

[0104] Characterization data of the compound of formula (I-1): 1 H NMR (500MHz, CDCl 2 CDCl 2 ,373K):δ=8.69-8.68(d,J=7.8Hz,4H),8.53-8.52(d,J=8.0Hz,2H),8.32-8.30(d,J=7.6Hz,2H),5.25- 5.19(m,1H),2.33-2.26(m,2H),2.00-1.94(m,2H),1.45-1.31(m,12H),0.92-0.89(m,6H)....

Embodiment 2

[0105] The preparation of embodiment 2 formula (I-2) compound

[0106] Under nitrogen protection, add 1,6-(4-tert-butyl)phenoxy 9-bromoperylene monoimide (237mg, 0.278mmol) represented by formula (III-2) into a sealed tube of 100mL , fullerene C60 (200mg, 0.278mmol), palladium acetate (4mg, 0.017mmol), tricyclohexylphosphine tetrafluoroborate (13mg, 0.034mmol), anhydrous potassium carbonate (153mg, 1.112mmol) and 8mL 1 -Methylnaphthalene, heated to 200°C, reacted for 3h, cooled to room temperature, the reaction solution was poured into methanol, the precipitate was collected by suction filtration, washed with methanol, dried, purified by silica gel column, and carbon disulfide was used as developing agent to obtain the formula (I- 2) Compound 178 mg, yield: 43%.

[0107]

[0108] Characterization data of the compound of formula (I-2): 1 H NMR (500MHz, CDCl 2 CDCl 2 ,373K):δ=9.68-9.66(d,J=8.0Hz,2H),8.37(s,2H),8.28-8.27(d,J=8.0Hz,2H),7.49-7.47(d,J=8.6 Hz,4H),7.20-7.18(d,...

Embodiment 3

[0109] The preparation of embodiment 3 formula (I-3) compound

[0110] Under nitrogen protection, add 1,6-(4-tert-butyl)phenylsulfanyl 9-bromoperylene monoimide (245mg, 0.278mmol) represented by formula (III-3) into a sealed tube of 100mL , fullerene C60 (200mg, 0.278mmol), palladium acetate (4mg, 0.017mmol), tricyclohexylphosphine tetrafluoroborate (13mg, 0.034mmol), anhydrous potassium carbonate (153mg, 1.112mmol) and 8mL 1 -Methylnaphthalene, heated to 200°C, reacted for 3h, cooled to room temperature, the reaction solution was poured into methanol, the precipitate was collected by suction filtration, washed with methanol, dried, purified by silica gel column, and carbon disulfide was used as developing agent to obtain the formula (I- 3) Compound 148 mg, yield: 35%.

[0111]

[0112] Characterization data of the compound of formula (I-3): 1 H NMR (500MHz, CDCl 2 CDCl 2 ,373K):δ=9.34-9.33(d,J=7.7Hz,2H),8.64(s,2H),8.43-8.41(d,J=7.8Hz,2H),7.43-7.39(m,8H), 5.09-5.05(m,1...

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Abstract

The invention proposes a perylene monoimide peri-fused fullerene derivative, a preparation method and an application thereof. The perylene monoimide peri-fused fullerene derivative has a structure shown in formula (I) or (II), and when the compound is used as an electron acceptor in an organic photovoltaic material, the photoelectric conversion efficiency is high, and it is a kind of Electron acceptor materials for organic photovoltaic cells with important application prospects.

Description

technical field [0001] The present invention belongs to the technical field of organic chemical synthesis. Specifically, the present invention relates to perylene monoimide peri-fused fullerene derivatives and a preparation method thereof, and also relates to the use of such compounds as electron acceptor materials in organic photovoltaic cells Applications. Background technique [0002] Since the discovery of fullerene (C60) in 1985, its unique structure has attracted the attention of scientists in the fields of physics, chemistry and biology. Fullerene derivatives (PCBM) obtained by chemically modifying fullerenes have been widely used in the field of organic photovoltaic cells. PCBM-like electron acceptor materials have many advantages, such as good solubility, high electron mobility, and good phase separation with common polymer donors, etc. However, PCBM-like materials have weak absorption in the visible light region. . In addition to fullerene acceptor compounds, so...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D221/18H01L51/42H01L51/46
CPCC07D221/18H10K85/6572H10K30/00Y02E10/549
Inventor 王朝晖冯嘉靖
Owner TSINGHUA UNIV
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