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Synthesis, preparation method and application of a tripterene-based perylene imide compound

A technology of perylene imide and tridecene, applied in the field of organic photovoltaic materials, can solve problems such as unreported

Active Publication Date: 2019-09-03
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] Compounds with tripterene as the backbone and peryleneimide as the substituent have not been reported.

Method used

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  • Synthesis, preparation method and application of a tripterene-based perylene imide compound
  • Synthesis, preparation method and application of a tripterene-based perylene imide compound
  • Synthesis, preparation method and application of a tripterene-based perylene imide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0064] Embodiment 1, the preparation of target product T-1-1

[0065] (1) Preparation of intermediate 1-1

[0066] In a sealed glass tube, add monobromoperyleneimide (Formula 1) (275mg, 0.395mmol), tripterene monoboronate (Formula 2-1) (100mg, 0.263mmol), THF 8ml and 2M sodium carbonate Aqueous solution 4ml. The mixture was sparged with argon for 30 min. Tetrakis(triphenylphosphine)palladium (36 mg, 0.032 mmol) was then added under argon. The mixture was heated to reflux for 48h, then cooled to room temperature, 25ml of water was added, extracted with dichloromethane (2×25ml), dried over anhydrous magnesium sulfate, filtered with suction, and the solvent was removed. The crude product was purified by chromatographic column to obtain a red solid, namely Intermediate 1-1 (225 mg, 90%). The reaction equation is as follows:

[0067]

[0068] The structural confirmation data of intermediate 1-1 are as follows: 1 H NMR (500MHz, C 2 D. 2 Cl 4 ,373.2K)δ=8.70-8.60(m,4H),8.5...

Embodiment 2

[0073] Embodiment 2, the preparation of target product T-2-1

[0074] (1) Preparation of intermediate 2-1

[0075]In a sealed glass tube, add monobromoperyleneimide (Formula 1) (345mg, 0.494mmol), tripterene bisborate (Formula 2-2) (100mg, 0.198mmol), 8ml of THF and 2M sodium carbonate Aqueous solution 4ml. The mixture was sparged with argon for 30 min. Tetrakis(triphenylphosphine)palladium (27 mg, 0.024 mmol) was then added under argon. The mixture was heated to reflux for 48h, then cooled to room temperature, 25ml of water was added, extracted with dichloromethane (2×25ml), dried over anhydrous magnesium sulfate, filtered with suction, and the solvent was removed. The crude product was purified by chromatographic column to obtain an orange solid (284mg , 87%), namely intermediate 2-1. The reaction equation is as follows:

[0076]

[0077] The structural confirmation data of intermediate 2-1 are as follows: 1 H NMR (500MHz, C 2 D. 2 Cl 4 ,373.2K)δ=8.71-8.58(m,10H)...

Embodiment 3

[0082] Embodiment 3, the preparation of target product T-3-1

[0083] (1) Preparation of intermediate 3-1

[0084] In a sealed glass tube, add monobromoperyleneimide (Formula 1) (353mg, 0.506mmol), triptene triborate (Formula 2-3) (100mg, 0.158mmol), tetrahydrofuran 8ml and 2M sodium carbonate Aqueous solution 4ml. The mixture was sparged with argon for 30 min. Tetrakis(triphenylphosphine)palladium (25 mg, 0.019 mmol) was then added under argon. The mixture was heated to reflux for 48h, then cooled to room temperature, 25ml of water was added, extracted with dichloromethane (2×25ml), dried over anhydrous magnesium sulfate, filtered with suction, and the solvent was removed. The crude product was purified by chromatographic column to obtain an orange solid (315mg , 85%), namely intermediate 3-1. The reaction equation is as follows:

[0085]

[0086] The structural confirmation data of intermediate 3-1 are as follows: 1 H NMR (500MHz, C 2 D. 2 Cl 4 ,373.2K)δ=8.73-8.6...

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Abstract

The present invention relates to the field of organic photovoltaic materials, in particular to a tripcene-based peryleneimide compound and its preparation method and application. The structural formula of the peryleneimide compound based on tripterene is shown as T-1, T-2 or T-3: wherein, R 1 Any group selected from the following: C 2‑60 Alkyl, substituted alkyl, alkoxy, substituted alkoxy, aryl, substituted aryl, alkylaryl, substituted alkylaryl, alkylhetero Aryl, substituted alkylheteroaryl, alkylheterocyclyl or substituted alkylheterocyclyl; R 1 same or different. The tripterene-based peryleneimide compound of the present invention obviously improves the photoelectric conversion efficiency, has reasonable and effective design ideas, simple molecular structure, and short synthesis steps, and is an organic solar cell material with important application prospects.

Description

technical field [0001] The invention relates to the field of organic photovoltaic materials, in particular to the synthesis, preparation method and application of a tripterene-based perylene imide compound. Background technique [0002] Solar energy is the safest, greenest and most ideal renewable clean energy for human beings. Organic photovoltaic cells use organic photovoltaic materials to prepare devices to achieve photoelectric conversion, and can be made into flexible large-area devices through solution processing technology, which has the advantages of light weight, low cost, and portability. Organic photovoltaic cells are an international cutting-edge interdisciplinary research field and have broad application prospects. [0003] Organic photovoltaic materials can be divided into electron donors and electron acceptors, and fullerene derivatives are currently the most widely used and most successful electron acceptors. However, due to the disadvantages of fullerene r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/08C07D519/00H01L51/46
CPCC07D471/08C07D519/00H10K85/6572Y02E10/549
Inventor 王朝晖孟东李燕姜玮
Owner INST OF CHEM CHINESE ACAD OF SCI
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