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1-(N-fluorinated phenyl)-3-fluorenyl pyrazoline fullerene C60 and preparation method thereof

A technology of fluorenylpyrazoline fullerene and fluorine-containing phenyl, which is applied in the field of 1--3-fluorenylpyrazoline fullerene C60 and its preparation, and can solve the problems affecting the fluorescence effect, etc.

Inactive Publication Date: 2013-07-24
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In addition, pyrazoline compounds have a special conjugated system. By changing the block structure on the pyrazoline ring, the electronic effect in the conjugated system can be changed, thereby affecting the fluorescence effect.

Method used

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  • 1-(N-fluorinated phenyl)-3-fluorenyl pyrazoline fullerene C60 and preparation method thereof
  • 1-(N-fluorinated phenyl)-3-fluorenyl pyrazoline fullerene C60 and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Example 1: Add 0.2 g of 2-fluorenaldehyde and 0.11 g of phenylhydrazine to a round bottom flask, use ethanol as the solvent, react at 70°C for half an hour, cool, filter and take the filter cake, and recrystallize to obtain 1-(N-phenyl) -3-Fluorenylhydrazone. Add 1-(N-phenyl)-3-fluorenylhydrazone 0.03g, C 60 0.036 g and 0.032 g of iodobenzene acetate were reacted at 40° C. for 5 hours with toluene as a solvent, and spin-dried to obtain a crude product. The crude product is separated by column chromatography with toluene / carbon disulfide as the eluent to obtain the target product 1-(N-phenyl)-3-fluorenylpyrazoline fullerene C 60 . Brown solid, yield: 33(70)%.

[0019] IR (KBr, cm-1): v 3442, 2920, 2851, 1592, 1490, 1027, 577, 525.

[0020] 1 H NMR (500 MHz, CS 2 – CDCl 3 ): δ 8.43 (s, 1H), 8.30 (d, J = 8.0 Hz, 1H), 7.94 (d, J = 7.5 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.77 (d, J = 7.5 Hz, 1H), 7.54 (d, J = 7.5 Hz, 1H), 7.45 (t, J = 8.0 Hz, 1H), 7.37 (t, J = 7.5 Hz,...

Embodiment 2

[0022] Example 2: Add 0.2 g of 2-fluorenaldehyde and 0.13 g of 3-fluorophenylhydrazine into a round-bottomed flask, use ethanol as the solvent, react at 70°C for half an hour, cool, filter to take the filter cake, and recrystallize to obtain 1'-(N -3-fluorophenyl)-3'-fluorenylhydrazone. Add 1'-(N-3-fluorophenyl)-3'-fluorenyl hydrazone 0.032g, C 60 0.036 g and 0.032 g of iodobenzene acetate were reacted at 40° C. for 5 hours with toluene as a solvent, and spin-dried to obtain a crude product. The crude product was separated by column chromatography using toluene / carbon disulfide as the eluent to obtain the target product 1'-(N-3-fluorophenyl)-3'-fluorenylpyrazoline fullerene C 60 . Brown solid, yield: 34(72)%.

[0023] IR (KBr, cm-1): v 3453, 2921, 2851, 1605, 1578, 1047, 573, 525.

[0024] 1 H NMR (500 MHz, CS 2 – CDCl 3 ): δ 8.41 (s, 1H), 8.28 (d, J = 7.5 Hz, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.78 (d, J = 7.5 Hz, 1H), 7.70 (td, J = 2.0 Hz, J = 1...

Embodiment 3

[0027] Example 3: Add 0.2 g of 2-fluorenaldehyde and 0.15 g of 2,5-difluorophenylhydrazine into a round-bottomed flask, use ethanol as the solvent, react at 70°C for half an hour, cool, filter the filter cake, and recrystallize to obtain 1' -(N-2,5-Difluorophenyl)-3'-fluorenylhydrazone. Add 1'-(N-2,5-difluorophenyl)-3'-fluorenylhydrazone 0.034g, C 60 0.036 g and 0.032 g of iodobenzene acetate were reacted at 40° C. for 5 hours with toluene as a solvent, and spin-dried to obtain a crude product. The crude product was separated by column chromatography using toluene / carbon disulfide as the eluent to obtain the target product 1'-(N-2,5-difluorophenyl)-3'-fluorenylpyrazolinefullerene C 60 . Brown solid, yield: 33(70)%.

[0028] IR (KBr, cm-1): v 3443, 2920, 2851, 1727, 1615, 1500, 1048, 574, 525.

[0029] 1 H NMR (500 MHz, CS 2 – CDCl 3 ): δ 8.36 (s, 1H), 8.24 (d, J = 8.0 Hz, 1H), 7.82 (d, J = 8.0 Hz, 1H), 7.74 (d, J = 7.5 Hz, 1H), 7.56-7.53 ( m, 1H),7.51 (d, J = 7.0 Hz, 1...

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Abstract

The invention relates to 1-(N-fluorinated phenyl)-3-fluorenyl pyrazoline fullerene C60 and a preparation method thereof. The structural formula of the compound is shown in the specification, wherein ArF is phenyl substituted by one to five fluoro groups. Due to a unique structure, the fullerene C60 disclosed by the invention has special physical and chemical properties. The C60 has a lowest unoccupied orbit with low energy and is an excellent electron acceptor, so that the C60 has an obvious quenching effect on fluorescence; and fluorescent derivatives of the C60 can serve as potential photovoltaic materials. According to the 1-(N-fluorinated phenyl)-3-fluorenyl pyrazoline fullerene C60 and the preparation method, a series of derivatives of the 1-(N-fluorinated phenyl)-3-fluorenyl pyrazoline fullerene C60 are obtained in a manner that the C60 and hydrazone are subjected to [3+2] cycloaddition reaction, the fluorescent properties of the derivatives are researched, and meanwhile, the influence on fluorescence of compounds caused by fluorine atoms are researched.

Description

technical field [0001] The present invention relates to 1-(N-fluorine-containing phenyl)-3-fluorenylpyrazoline fullerene C 60 and its preparation method. technical background [0002] Fullerene C 60 It is a new class of spherical molecules whose size is in the range of tens of nanometers. Because of its unique structure, it has special physical and chemical properties. C 60 It has the lowest empty orbital with lower energy, can accept 6 electrons, and is an excellent electron acceptor. Studies have shown that C 60 It has obvious quenching effect on fluorescence, and its fluorescent derivatives can be used as potential photovoltaic materials. [0003] In addition, pyrazoline compounds have a special conjugated system. By changing the block structure on the pyrazoline ring, the electronic effect in the conjugated system can be changed, thereby affecting the fluorescence effect. In this paper, by containing 1-(N-fluorine-containing phenyl)-3-fluorenyl hydrazone and C 60...

Claims

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Application Information

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IPC IPC(8): C07D231/54C09K11/06
Inventor 何珊珊章建民邹元海成浩楠沈苏波
Owner SHANGHAI UNIV
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