Synthesis and preparation method and applications of triptycene-based perylene imide compound

A technology of peryleneimide and tripterene, which is applied in the field of organic photovoltaic materials and can solve problems that have not been reported

Active Publication Date: 2018-08-21
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Compounds with tripterene as the backbone an...

Method used

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  • Synthesis and preparation method and applications of triptycene-based perylene imide compound
  • Synthesis and preparation method and applications of triptycene-based perylene imide compound
  • Synthesis and preparation method and applications of triptycene-based perylene imide compound

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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 invention relates to the field of organic photovoltaic materials, particularly to a triptycene-based perylene imide compound, a preparation method and applications thereof, wherein the triptycene-based perylene imide compound has the structure formula represented by T-1, T-2 or T-3, and R1 are selected from the following any groups: C2-60 alkyl, substituent-containing alkyl, alkoxy, substituent-containing alkoxy, aryl, substituent-containing aryl, alkyl aryl, substituent-containing alkyl aryl, alkyl heteroaryl, substituent-containing alkyl heteroaryl, alkyl heterocycle group and substituent-containing alkyl heterocycle group, and are the same or different. According to the present invention, with the triptycene-based perylene imide compound, the photoelectric conversion efficiency is significantly improved, the design idea is reasonable and effective, the molecular structure is simple, and the synthesis step is short; and the triptycene-based perylene imide compound is the organicsolar cell material with important application prospects. The formulas T-1, T-2 and T-3 are defined in the specification.

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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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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