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Gear type heterocyclic tripolyperylene tetracarboxylic acid diimide compound and preparation method and application thereof

A polyperylene diimide and gear type technology is applied in the field of gear type heterocyclic trimer perylene diimide compounds and their preparation, and achieves the effects of inhibiting force, shortening synthesis steps and improving photoelectric conversion efficiency

Active Publication Date: 2017-10-24
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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  • Gear type heterocyclic tripolyperylene tetracarboxylic acid diimide compound and preparation method and application thereof
  • Gear type heterocyclic tripolyperylene tetracarboxylic acid diimide compound and preparation method and application thereof
  • Gear type heterocyclic tripolyperylene tetracarboxylic acid diimide compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The preparation of embodiment 1 target product 1

[0047] (1) Preparation of Intermediate 1

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

[0049]

[0050] in,

[0051] The structural confirmation data of intermediate 1 are as follows: 1 H NMR (400MHz, CDCl ...

Embodiment 2

[0071] The preparation of embodiment 2 target product 2

[0072] The chemical structural formula of the target product 2 that the present embodiment obtains is as follows:

[0073]

[0074] in,

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

[0076] The structure confirmation data of the target product 2 are 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 C NMR (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, 26AL.53, 22.7783, 13% (MS ):C 144 h 150 N 6 o 12 Theoretical value of Se3: 2392.88791; measured value: 2392.88783.

[0077] The photoelectric conversion performance test of target product 2 is identical with embodiment 1, and the photovoltaic pe...

Embodiment 3

[0079] (1) A mixture of monobromoperyleneimide and 1,3,5-benzenetriborate with a molar ratio of 3:1 is mixed and dissolved in tetrahydrofuran and aqueous sodium carbonate solution by argon blowing, wherein the concentration of sodium carbonate 2mol / L, the volume ratio of tetrahydrofuran and sodium carbonate aqueous solution is 1.8:1, then under argon gas, the catalyst is tetrakis (triphenylphosphine) palladium, mixed and heated to reflux to obtain orange solid intermediate 1;

[0080]

[0081] where R 1 for

[0082] (2) Intermediate 1, I 2 The mixture with toluene was irradiated under a mercury lamp, then extracted with saturated aqueous sodium sulfite, washed, dried, filtered, and chromatographically purified to obtain 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 11h, wherein the volume ratio of fuming nitric acid to dichlorome...

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Abstract

The invention provides a gear type heterocyclic tripolyperylene tetracarboxylic acid diimide compound. The structural formula of the compound is as shown in the formula (I), wherein R1 is selected from any one of the following groups: C2-60 alkyl, substituent containing alkyl, alkoxy, substituent-containing alkoxy, aryl, substituent-containing aryl, alkyl aryl, substituent-containing alkyl aryl, alkyl heteroaromatic groups, substituent containing alkyl heteroaromatic groups, alkyl heterocyclic groups or substituent containing alkyl heterocyclic groups, and R1 in different positions is the same or different; R2 is selected from S or Se, and R2 in different positions is the same or different. According to the gear type heterocyclic tripolyperylene tetracarboxylic acid diimide compound disclosed by the invention, heteroatoms are introduced in six positions of 6, 7, 6', 7', 6'' and 7'' of single bonded tripolyperylene tetracarboxylic acid diimide to obviously improve the photoelectric conversion efficiency, and the gear type heterocyclic tripolyperylene tetracarboxylic acid diimide compound is reasonable and effective in design idea, simple in molecular structure and shortened in synthesis step, and further 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 trimerized perylene diimide compound and its preparation method and application. 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 fu...

Claims

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Application Information

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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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