Bay area cyclization synthesis method for perylene bisimide derivative

A technology of perylene bisimide and synthesis method, which is applied in the field of cyclization synthesis of perylene bisimide derivatives, can solve problems such as unsatisfactory yield, achieve good remodification ability, simple reaction steps, Amplify the effect of conjugated systems

Inactive Publication Date: 2016-11-23
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, the chlorine atom introduced by the ring expansion reaction of a common perylene derivative has an unsatisfactory yield in the subsequent coupling reaction

Method used

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  • Bay area cyclization synthesis method for perylene bisimide derivative
  • Bay area cyclization synthesis method for perylene bisimide derivative
  • Bay area cyclization synthesis method for perylene bisimide derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0049] Dissolve 0.37 g of A in 200 ml of dichloromethane, add dropwise a dichloromethane solution containing 0.34 g of iodine monobromide under the protection of argon, and stir at -78°C for 1 hour. The reacted liquid was naturally warmed to room temperature, stirred for 3 hours, and then illuminated for 24 hours. After the reaction, quench the reaction with a dilute solution of sodium sulfite, dry with anhydrous magnesium sulfate, filter, remove the solvent, use 300-400 mesh silica gel column chromatography, and the eluent is petroleum ether: dichloromethane = 2:1, to obtain Orange-yellow solid B 0.31 g, yield 76%. The H NMR spectrum and mass spectrum of compound B are shown in image 3 and Figure 4 .

Embodiment 2

[0051]0.20 g of compound B was dissolved in 100 ml of dichloromethane, and under argon protection, a dichloromethane solution containing 0.13 g of iodine monochloride was added dropwise, and stirred at room temperature for 6 hours. After the reaction, quench the reaction with a dilute solution of sodium sulfite, dry with anhydrous magnesium sulfate, filter, remove the solvent, and use 300-400 mesh silica gel column chromatography, the eluent is petroleum ether: dichloromethane = 2:1, to obtain Orange-yellow solid C 0.18 g, yield 86%. The H NMR spectrum and mass spectrum of compound C are shown in Figure 5 and Figure 6 .

Embodiment 3

[0053] Add 0.15 g of compound C, 0.10 g of 3,4,5-trifluorophenylboronic acid, and 0.03 g of tetrakistriphenylphosphine palladium to a mixed solution of 5 ml of dilute potassium carbonate solution and 5 ml of tetrahydrofuran, under the protection of argon Heat to reflux and condense for 16 hours. After cooling to room temperature, extract three times with dichloromethane, dry the organic phase with anhydrous magnesium sulfate, remove the solvent, and use 300-400 mesh silica gel column chromatography, the eluent is petroleum ether: dichloromethane = 2:1, to obtain Orange-yellow solid D 0.15 g, yield 95%. The H NMR spectrum and mass spectrum of compound D are shown in Figure 7 and Figure 8 , whose UV-visible spectrum is shown in Figure 9 , the fluorescence spectrum see Figure 10 .

[0054] Referring to compounds with similar structures (see: Org.Lett., 2012, 14(17): 4654-4657), the total yield of the coupling step of this compound in the literature is less than 60%, and ...

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Abstract

The present invention relates to the technical field of organic synthesis, and specifically relates to a new bay area cyclization synthesis method of perylene bisimide derivatives, which uses bay area silynylated perylene bisimide as a raw material, and obtains the target product through two-step reactions. The product expands the derivatization reaction of perylene bisimides, ensures the planar structure of perylene bisimides to the greatest extent, provides an effective ring expansion method, and has the advantages of simple synthesis steps, easy-to-obtain raw materials, and subsequent coupling reactions. The advantages such as high efficiency, the subsequent coupling reaction broadens the application of perylene compounds.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a novel bay area ring-forming synthesis method of perylene bisimide derivatives. Background technique [0002] Perylenebisimide derivatives are widely used in the fields of industrial dyes and molecular optoelectronic devices. As an important class of functional materials, they have many advantages, such as stable structure and good thermal stability. The light in the infrared region has strong absorption and the fluorescence quantum yield is high, which makes it widely used in organic solar cells, organic solid-state photovoltaic devices, organic field effect transistors and other fields. Therefore, the derivatization reaction of perylene bisimide becomes particularly important. Among them, the ring expansion reaction can increase the conjugated π system of perylene derivatives, thereby effectively adjusting the photoelectric properties of such derivatives. an importa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C09K11/06
CPCC07D471/06C09K11/06C09K2211/1029
Inventor 张隽佶毛文轩田禾
Owner EAST CHINA UNIV OF SCI & TECH
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