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Saddle-shaped perylene diimide tetramer, and preparation method and application thereof

A peryleneimide tetramer and saddle-shaped technology, which is applied in the field of saddle-shaped peryleneimide tetramer and its preparation, can solve the problems of low photoelectric conversion efficiency and easy aggregation of peryleneimide derivatives, and achieve Effects of preventing close packing, improving performance, and suppressing crystallinity

Active Publication Date: 2019-04-02
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved in the present invention is: in order to solve the technical problem that the existing perylene imide derivatives are easy to aggregate and the photoelectric conversion efficiency is low, a saddle-type perylene imide tetramer and its preparation method and application are provided

Method used

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  • Saddle-shaped perylene diimide tetramer, and preparation method and application thereof
  • Saddle-shaped perylene diimide tetramer, and preparation method and application thereof
  • Saddle-shaped perylene diimide tetramer, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0046] (1) Preparation of intermediate compound (Ⅳ)

[0047] The compound (225mg, 0.34mmol, 1.0eq) of the structure shown in formula III was added to 100mL Schlenk, vacuum-dried for 0.5h, during which the argon gas was changed 3 times, 30mL tetrahydrofuran was added, and under the protection of Ar gas at -78°C, drop Add n-BuLi (1.4mL, 2.5M in hexane, 3.49mmol, 10.0eq), slowly raise the temperature to 60°C, and react for 3h; add Sn(C 4 h 9 ) 3 Cl (0.76mL, 2.8mmol, 8.0eq), slowly warmed up to room temperature, and reacted overnight. Add 1mLCH at -78°C 3 OH quenches the reaction. Transfer the reaction system to a 250mL separatory funnel, separate the aqueous phase, and use 3×15mL CH 2 Cl 2 The aqueous phase is extracted and the organic phases are combined. The organic phase was washed with 3 x 15 mL of water and washed with anhydrous MgSO 4 After drying, filtering, and removing the solvent, 1.131 g of compound (IV) was obtained.

[0048]

[0049] (2) Preparation of sa...

Embodiment 2

[0059] (1) Preparation of intermediate compound formula (Ⅳ)

[0060] Add the compound (226mg, 0.34mmol, 1.0eq) of the structure shown in formula III-B into 100mL Schlenk, vacuum-dry for 0.5h, change nitrogen 3 times during this period, add 30mL tetrahydrofuran, and drop Add t-BuLi (1.12mL, 2.5M in hexane, 2.79mmol, 8.0eq), slowly raise the temperature to 50°C, and react for 3h; add Sn(C 4 h 9 ) 3 Cl (0.57mL, 2.1mmol, 6.0eq), slowly warmed up to room temperature, and reacted overnight. The reaction was quenched by adding 1 mL of saturated sodium bicarbonate solution at -90°C. Transfer the reaction system to a 250mL separatory funnel, separate the aqueous phase, and wash with 3×15mL CHCl 3 The aqueous phase is extracted and the organic phases are combined. The organic phase was washed with 3 x 15 mL of water and washed with anhydrous MgSO 4 Dry, filter, and remove the solvent to obtain 1.131 g of compound (IV-B).

[0061]

[0062] (2) Preparation of saddle type perylen...

Embodiment 3

[0072] (1) Preparation of intermediate compound (Ⅳ)

[0073] Add the compound (225mg, 0.34mmol, 1.0eq) of the structure shown in formula III into 100mL Schlenk, vacuum-dry for 0.5h, change helium 3 times during this period, add 30mL tetrahydrofuran, -60℃ under the protection of helium, drop Add n-BuLi (1.68mL, 2.5M in hexane, 4.19mmol, 12.0eq), slowly raise the temperature to 70°C, and react for 3h; add Sn(C 4 h 9 ) 3 Cl (0.95mL, 3.5mmol, 10.0eq), slowly warmed up to room temperature, and reacted overnight. Add 1mL CH at -60°C 3 OH quenches the reaction. Transfer the reaction system to a 250mL separatory funnel, separate the aqueous phase, and use 3×15mL CH 2 Cl 2 The aqueous phase is extracted and the organic phases are combined. The organic phase was washed with 3 x 15 mL of water and washed with anhydrous MgSO 4 After drying, filtering, and removing the solvent, 1.131 g of compound (IV) was obtained.

[0074]

[0075] (2) Preparation of saddle-shaped perylene im...

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Abstract

The invention relates to a saddle-shaped perylene diimide tetramer, and a preparation method and an application thereof. According to the saddle-shaped perylene diimide tetramer provided by the invention, with cyclooctatetetraene as a building unit, the carbon-carbon double bond of the cyclooctatetraene is fused with a heterocyclic group to form a structure which is used as a mother nucleus, and four perylene diimides are coupled at the active site of the heterocyclic group to form a novel perylene diimide tetramer; meanwhile, a perylene diimide tetramer with ring closure through photochemicaloxidation is further provided. The saddle-shaped perylene diimide tetramer provided by the invention solves the technical problems of easy aggregation and low photoelectric conversion efficiency fora conventional perylene diimide derivative, and can be used as an acceptor material to be applied in organic solar cells.

Description

technical field [0001] The invention relates to a saddle-shaped perylene imide tetramer, a preparation method and application thereof, and belongs to the technical field of organic photovoltaic materials. Background technique [0002] In order to alleviate the pressure brought by the current energy crisis, countries all over the world have paid attention to the utilization of clean energy. Among them, organic solar cells have attracted attention due to their advantages such as low cost, light weight, good flexibility, and large-area printing preparation. The energy conversion efficiency of organic solar cells has been gradually improved, indicating a bright prospect for the commercialization of organic solar cells. [0003] Organic photovoltaic materials are divided into donor materials and acceptor materials. Among them, fullerene derivatives are widely used as electron acceptors due to their unique structure and high performance, but their cost is high, and their absorptio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/22C07D517/22C07D519/00H01L51/46
CPCC07D495/22C07D517/22C07D519/00H10K85/621H10K85/657H10K85/6576Y02E10/549Y02B10/10
Inventor 宋金生杨丽思王华
Owner HENAN UNIVERSITY
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