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A kind of gear type heterocyclic trimerized perylene diimide compound and its preparation method and application

A technology of polyperylene diimide and monobromo perylene diimide is applied in the field of gear-type heterocyclic trimer perylene diimide compound and preparation thereof, and achieves inhibition force, reasonable and effective design idea, and simple molecular structure Effect

Active Publication Date: 2019-08-20
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The first object of the present invention is to provide a gear-type heterocyclic trimer perylene diimide compound to solve the molecular aggregation caused by the strong force between molecules of traditional perylene imide molecules in the solid state, Effectively improves the efficiency of the device

Method used

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  • A kind of gear type heterocyclic trimerized perylene diimide compound and its preparation method and application
  • A kind of gear type heterocyclic trimerized perylene diimide compound and its preparation method and application
  • A kind of gear type heterocyclic trimerized perylene diimide compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1 Preparation of target product 1

[0047] (1) Preparation of Intermediate 1

[0048] In the glass tube, add monobromoperylene imide (compound of formula a) (546g, 0.702mmol), 1.3.5-benzene triborate (compound of formula b) (100mg, 0.219mmol), 8ml of tetrahydrofuran and 2M carbonic acid 4ml sodium aqueous solution, mixed with nitrogen gas for 30min, then under argon, add tetrakis(triphenylphosphine)palladium (35mg, 0.026mmol), the mixture is heated to reflux for 48h, then cooled to room temperature, 25ml water is added, and dichloride Methane (2×25ml) was extracted, dried with anhydrous magnesium sulfate, filtered with suction, and the solvent was removed. The crude product was purified by a chromatographic column to obtain intermediate 1 (367mg, yield 80%) as an orange solid. The reaction equation is as follows:

[0049]

[0050] among them,

[0051] The structural confirmation data of Intermediate 1 are as follows: 1 H NMR(400MHz, CDCl 3 )δ=8.67(m,21H), 8.05(s,3H), ...

Embodiment 2

[0071] Example 2 Preparation of target product 2

[0072] The chemical structural formula of the target product 2 obtained in this embodiment is as follows:

[0073]

[0074] among them,

[0075] The preparation method of the target product 2 is the same as in Example 1, except that the S powder in step (4) is replaced with Se powder, and other conditions remain unchanged.

[0076] The structure confirmation data of target product 2 is as follows: 1 H NMR(400MHz, CDCl 3 )δ=9.94(s,6H),9.83(s,6H),5.16(m,6H),2.15-2.09(m,12H),1.95(m,12H),1.30-1.24(m,72H),0.79 (s,36H); 13 CNMR(100MHz, CDCl 3 ): δ=164.77,164.21,142.05,134.67,130.99,128.94,128.40,127.42,124.18,123.82,122.38,122.16,55.03,32.24,31.53,31.38,26.53,22.33,13.78,13.74; HRMS(MALDI, 100% ): C 144 H 150 N 6 O 12 Se3 theoretical value: 2392.88791; measured value: 2392.88783.

[0077] The photoelectric conversion performance test of the target product 2 is the same as that of Example 1. The photovoltaic performance of the device is sho...

Embodiment 3

[0079] (1) A mixture of monobromoperylene imide and 1,3,5-benzene triborate in a molar ratio of 3:1 was mixed and dissolved in tetrahydrofuran and sodium carbonate aqueous solution through argon gas blowing. The concentration of sodium carbonate It is 2mol / L, the volume ratio of tetrahydrofuran to sodium carbonate aqueous solution is 1.8:1, and then under the condition of argon gas and tetrakis(triphenylphosphine)palladium, the mixture is heated and refluxed to obtain orange solid intermediate 1;

[0080]

[0081] Where R 1 for

[0082] (2) Intermediate 1, I 2 The mixture with toluene is irradiated under a mercury lamp, and then extracted with a saturated aqueous sodium sulfite solution, washed, dried, filtered, and purified by chromatography to obtain a dark red solid intermediate 2;

[0083]

[0084] Where R 1 for

[0085] (3) Add the dichloromethane solution of fuming nitric acid to Intermediate 2 and dichloromethane to react for 11 hours, where the volume ratio of fuming nitric ...

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Abstract

The present invention provides a gear-type heterocyclic trimer perylene diimide compound, the structural formula of which is shown in formula (I): wherein, R 1 Any one of the following groups: C 2‑60 Alkyl, substituted alkyl, alkoxy, substituted alkoxy, aryl, substituted aryl, alkylaryl, substituted alkylaryl, alkylhetero Aryl group, alkyl heteroaryl group containing substituent, alkyl heterocyclic group or alkyl heterocyclic group containing substituent, R in each position 1 same or different; R 2 Selected from S or Se, R at each position 2 same or different. The gear-type heterocyclic trimerized perylene diimide of the present invention introduces heteroatoms at six positions of 6, 7, 6', 7', 6", and 7" of the single bonded trimerized perylene diimide, The photoelectric conversion efficiency is obviously improved, the design idea is reasonable and effective, the molecular structure is simple, and the synthesis steps are shortened. It 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 a gear type heterocyclic trimerperylene diimide compound and a preparation method and application thereof. Background technique [0002] Solar energy is the safest, greenest and most ideal renewable clean energy for mankind. Organic photovoltaic cells use organic photovoltaic materials to prepare devices to achieve photoelectric conversion. They can be made into flexible large-area devices through solution processing technology, and have the advantages of light weight, low cost, and portability. Organic photovoltaic cells are an international cutting-edge cross-research field with broad application prospects. [0003] Organic photovoltaic materials can be divided into electron donors and electron acceptors. Fullerene derivatives are currently the most widely used and most successful electron acceptors. However, due to the shortcomings of fullerene receptors such as weak a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/22C07D517/22C09K11/06H01L51/46
CPCC09K11/06C07D495/22C07D517/22C09K2211/1029C09K2211/1096C09K2211/1092H10K85/657Y02E10/549
Inventor 王朝晖孟东李燕姜玮
Owner INST OF CHEM CHINESE ACAD OF SCI
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