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A kind of spiro ring aromatic fused ring imide compound and preparation method thereof

A spiro-aromatic fused-ring imide and a technology of fused-ring imide, which are applied in the field of new spiro-aromatic fused-ring imide compounds and their preparation, can solve the problem of increased synthesis difficulty, spiro-aromatic fused-ring acyl Imine compounds have not been developed and other problems, to achieve the effect of simple reaction conditions and high product yield

Active Publication Date: 2019-09-17
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the difficulty of synthesizing the existing fused-ring imide compounds increases with the increase of the degree of conjugation, and the spiro-aromatic fused-ring imide compounds have not been developed.

Method used

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  • A kind of spiro ring aromatic fused ring imide compound and preparation method thereof
  • A kind of spiro ring aromatic fused ring imide compound and preparation method thereof
  • A kind of spiro ring aromatic fused ring imide compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1, the preparation of the compound of formula (I-1) Under the protection of nitrogen, add the perylene imide (778mg, 1mmol), 0.1mmol Palladium acetate, 5mmol sodium carbonate, 1mmol dibromomethane and 30ml dioxane, heated to 80°C, reacted for 8h, cooled to room temperature, poured the reaction solution into water, collected the precipitate by suction filtration, washed with water, dried, and purified by silica gel column , dichloromethane / petroleum ether as a developing solvent to obtain 623 mg of the compound of formula (I-1), yield: 80%. The reaction formula is as follows:

[0045]

[0046] Characterization data of formula (Ⅰ-1) compound ( Figure 1 to Figure 3 ):1 H NMR (400MHz, CDCl 3 ,300K)δ=8.81(dd,4H),8.73(d,4H),8.09(d,4H),5.20-5.12(m,4H),2.27(m,4H),2.15-2.13(m,4H) ,1.76(m,8H),1.23(m,48H),0.80(m,24H); 13 C NMR (100MHz, CDCl 3 ,273K):δ=165.36,164.42,164.17,163.30,141.83,138.73,135.07,133.35,132.56,129.70,127.56,126.70,124.98,124.79,124.08,123.84...

Embodiment 2

[0047] Embodiment 2, the preparation of formula (I-2) compound

[0048] Under nitrogen protection, in the 100ml two-necked bottle, add the perylene imide (664mg, 1mmol) that has monobromine substitution shown in formula (II-2), the palladium acetate of 0.1mmol, 5mmol sodium carbonate, 1mmol methylene bromide and 30ml Dioxane, heated to 80°C, reacted for 8h, cooled to room temperature, poured the reaction liquid into water, collected the precipitate by suction filtration, washed with water, dried, purified on a silica gel column, and used dichloromethane / petroleum ether as a developing solvent to obtain the formula (I-2) Compound 525mg, Yield: 79%. The reaction formula is as follows:

[0049]

[0050] Characterization data of formula (Ⅰ-2) compound ( Figure 4 to Figure 6 ): 1 H NMR (400MHz, CDCl 3 ,328.2K)δ=8.79(d,4H),8.71(d,4H),8.09(s,4H),5.21(m,4H),2.22(m,8H),1.79-1.72(m,8H), 1.36-1.25(m,16H),0.89(t,24H); 13 C NMR (100MHz, CDCl 3 ,328.2K):δ=165.73,164.81,163.74,142...

Embodiment 3

[0051] Embodiment 3, the preparation of formula (I '-1) compound

[0052] Under nitrogen protection, add monobromo-substituted condensed cyclic imide (900mg, 1mmol), 0.1mmol of palladium acetate, 5mmol of sodium carbonate, 1mmol of dibromomethane into a 100ml two-necked flask and 30ml of dioxane, heated to 80°C, reacted for 8h, cooled to room temperature, poured the reaction liquid into water, collected the precipitate by suction filtration, washed with water, dried, and purified by silica gel column, using dichloromethane / petroleum ether as developing solvent, 495 mg of the compound of formula (I'-1) was obtained, yield: 55%. The reaction formula is as follows:

[0053]

[0054] Characterization data of formula (I'-1) compound ( Figure 7 to Figure 9 ): 1 H NMR (500MHz, CDCl 2 CDCl 2 ,373K)δ=8.78-8.73(m,6H),8.67-8.62(m,6H),8.34-8.33(d,2H),8.20-8.18(d,4H),8.06(s,2H),5.10- 5.06(m,4H),2.17-2.12(m,8H),1.86-1.81(m,8H),1.28-1.18(m,80H),0.82-0.76(m,24H); 13 C NMR (125MHz, ...

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Abstract

The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a novel spiro-ring aromatic fused-ring imide compound and a preparation method thereof. Described spiro-ring aromatic fused ring imide compound has the structural formula shown in formula (I) or formula (I'), wherein, R 1 from C 2‑60 Any group, the group is an alkyl group, a substituent-containing alkyl group, an alkoxy group, a substituent-containing alkoxy group, an aryl group, a substituent-containing aryl group, an alkylaryl group, a substituent-containing group Alkylaryl, alkylheteroaryl, substituted alkylheteroaryl, alkylheterocyclyl, substituted alkylheterocyclyl, R 1 same or different. When the spirocyclic aromatic fused imide compound provided by the present invention is used as an electron acceptor in an organic photovoltaic material, the photoelectric conversion efficiency is high, and it is an electron acceptor material of an organic photovoltaic cell with important application prospects or used in organic LED material.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a novel spiro-ring aromatic fused-ring imide compound and a preparation method thereof. Background technique [0002] When non-renewable energy sources such as natural gas, coal, and oil are running out frequently, and energy issues have increasingly become a bottleneck restricting the development of the international society and economy, more and more countries have begun to develop solar energy resources and seek new impetus for economic development. Driven by the huge potential of the international photovoltaic market, the solar cell manufacturing industries of various countries are scrambling to invest huge sums of money and expand production in order to compete for a place. Solar photovoltaic power generation will occupy an important seat in the world's energy consumption in the near future, not only to replace some conventional energy sources,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/22H01L51/54H01L51/46
CPCC07D471/22H10K85/6572Y02E10/549
Inventor 王朝晖高广鹏冯嘉靖姜玮
Owner INST OF CHEM CHINESE ACAD OF SCI