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1, 6, 7, 12-tetraphenyl perylene bisimide derivant and preparation method thereof

A technology of tetraphenyl perylene bisimide and perylene bisimide, which is applied in the field of organic photoelectric functional materials, and achieves the effect of good solubility

Inactive Publication Date: 2010-03-10
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But so far, relevant 1,6,7,12-tetraphenylperylenebisimide derivatives and preparation methods thereof have not been reported yet

Method used

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  • 1, 6, 7, 12-tetraphenyl perylene bisimide derivant and preparation method thereof
  • 1, 6, 7, 12-tetraphenyl perylene bisimide derivant and preparation method thereof
  • 1, 6, 7, 12-tetraphenyl perylene bisimide derivant and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The preparation of embodiment 1 compound 6

[0019]

[0020] Add 1g (1mmol) 1, 1g (2.5mmol) bis(trifluoroacetic acid) iodobenzene and 252mg elemental iodine to a 100ml two-necked flask, react at room temperature in carbon tetrachloride for 3h, separate by column chromatography to obtain 2(840mg, produce rate of 60%). MS: m / z: 1422 ([M] + ).

[0021]

[0022] Add 1.0g (0.7mmol) intermediate 2, 59mg (0.084mmol) [PdCl2 (PPh3) 2], 66.7mg (0.35mmol) CuI and 91.8mg (0.35mmol) PPh to the 50ml two-necked bottle 3 , then add 20ml of triethylamine and 10ml of THF, add 0.45ml of trimethylsilylacetylene under the protection of nitrogen, stir at room temperature for 24h, then pour into dichloromethane, filter, and obtain pure product by column chromatography, and then this pure 800mg (0.63mmol) of the product was mixed with 186.5mg (5.04mmol) of ammonium fluoride and 24.7mg (0.09mmol) of n-butylammonium fluoride, reacted in tetrahydrofuran solution at room temperature for 3...

Embodiment 2

[0027] The preparation of embodiment 2 compound 8

[0028]

[0029] 500mg (0.49mmol) of intermediate 3 and 2.76g (3mmol) of 7 were reacted in o-xylene at 160°C for 50h under nitrogen protection. Then cooled to room temperature, the solvent was removed under reduced pressure, and the target compound was separated by column chromatography 1.94g (85%) MS (MALDI-TOF): m / z: 4657.5 ([M+H] + ).

Embodiment 3

[0030] The preparation of embodiment 3 compound 10

[0031]

[0032] 100mg (0.1mmol) of intermediate 3 and 446.4mg (0.6mmol) of 9 were reacted in o-xylene at 170°C for 48h under nitrogen protection. Then it was cooled to room temperature, the solvent was removed under reduced pressure, and 271.5 mg (70%) of the target compound was separated by column chromatography. MS (MALDI-TOF): m / z: 3879 ([M+H] + ).

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Abstract

The invention relates to a 1, 6, 7, 12-tetraphenyl perylene bisimide derivant and a preparation method thereof, belonging to the field of organic photoelectronic functional material preparation. The structural characteristic of the perylene bisimide derivant is that 1, 6, 7, 12-four harbor positions of 3, 4, 9, 10-perylene bisimide are connected with charge transport functional groups with different structure types and different conjugation degrees by phenyls. The derivant is synthesized by the following steps: firstly, a perylene bisimide core with terminal ethyne or halogen or other active groups at the periphery is synthesized by 1, 6, 7, 12-tetraphenyl perylene; and then the 1, 6, 7, 12-tetraphenyl perylene bisimide and cyclopentadienyl ketone with functional substitute group at periphery or arylamine and the like generate Diels-Alder cycloaddtion or C-N, C-C coupling reaction and the like, thus obtaining the target derivant. The compound has excellent thermal stability and morphologic stability and dissolvability; the opto-electronic property of the compound has obvious bathochromic shift compared with other perylene bisimide derivants; and the derivant can be widely applied in the fields of photoelectron and biology such as organic electroluminescence, solar cell, near-infrared fluorescence probe and the like.

Description

technical field [0001] The invention relates to a class of 1,6,7,12-tetraphenylperylene bisimide derivatives in the field of organic photoelectric functional materials and a preparation method thereof. Background technique [0002] Since Friedlander synthesized perylene bisimide compounds in 1913 (German Patent 1913, 276, 956), perylene bisimide dyes have been widely used for their superior dyeing performance, stability and light fastness. The dye and coating industry, due to its excellent planarity, high stability and unique photoelectric properties, has attracted much attention in the field of design and synthesis of functional materials in recent years, such as solar cells, organic field effect tubes, electroluminescent materials , liquid crystal materials and bioluminescent probes and other fields of research reports are extremely active (Angew.Chem., Int.Ed.2004, 43, 6363.; J.Am.Chem.Soc.2003, 125; J.Am.Chem. Soc. 2003, 125, 437.; J. Org. Chem. 2005, 3715.;). Therefor...

Claims

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Application Information

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IPC IPC(8): C07D471/06C09K11/06
CPCC09B5/62
Inventor 李久艳刘迪任辉彩陶茜
Owner DALIAN UNIV OF TECH
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