Trifluorophenyl-containing dithiophene derivative and preparation method thereof

A trifluorophenyl bisthiophene and trifluorophenyl technology are applied in the field of trifluorophenyl bisthiophene derivatives and their preparation, and can solve the problems affecting emission wavelength, luminous efficiency and service life, and electron cloud density of bisthiophene compounds. Changes, complex synthesis steps and other problems, to achieve the effect of favorable electronic transition and energy transfer, good photoelectric activity, and simple synthesis steps

Inactive Publication Date: 2019-09-06
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Chinese patent 200910112709.X introduces an organic fluorescent material of glutamic acid derivatives, which emits blue fluorescence under ultraviolet light around 330nm, but its preparation conditions are relatively harsh
Chinese patent 200610124795.2 introduces an organic fluorescent material of pyridine derivatives, which can be used as a fluorescent probe in analysis and biochemistry, but it is a fluorescent composition material with rare earth metals, and the preparation price is relatively expensive
Chinese patent 200810162059.5 introduces an organic fluorescent material of naphthooxazole derivatives, which has a high fluorescence quantum yield, but its synthesis steps are cumbersome
The introduction of absorbing or donating electron groups will change the overall electron cloud density of bisthiophene compounds, which will affect the energy level structure of its conjugated π electron system, thereby affecting its maximum emission wavelength, luminous efficiency and service life.

Method used

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  • Trifluorophenyl-containing dithiophene derivative and preparation method thereof
  • Trifluorophenyl-containing dithiophene derivative and preparation method thereof

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Effect test

Embodiment 1

[0021] Weigh 5,5-dibromo-2,2-dithiophene (0.324g1.0mmol), 3,4,5-trifluorophenylboronic acid (0.528g3.0mmol), tetrakis(triphenylphosphine)palladium (0.0462g0 .04mmol), salt of wormwood (2.08g15mmol) is mixed in the reaction device of 100mL, this reaction device is filled with nitrogen after vacuumizing, and repeats this operation three times, adds the mixed solution of 20mL toluene, 10mL ethanol, 2.0mL water after, in Under the protection of nitrogen, microwave reflux reaction for 2 hours; after the reaction solution is cooled, separate the liquids, extract with dichloromethane, combine the organic phases, wash with saturated brine and dry with magnesium sulfate to remove water; use a rotary evaporator to remove the solvent to obtain a solid powder , and then use pure petroleum ether as eluent to carry out column separation to obtain light yellow solid powder, which is recrystallized in petroleum ether to obtain light yellow blocky crystals.

Embodiment 2

[0023] Weigh 5,5-dibromo-2,2-dithiophene (0.162g0.5mmol), 3,4,5-trifluorophenylboronic acid (0.176g1.0mmol), tetrakis(triphenylphosphine)palladium (0.0578g0 05mmol), salt of wormwood (0.690g5mmol) is mixed in the reaction device of 100mL, this reaction device is filled with nitrogen after vacuumizing, and repeats this operation three times, then adds the mixed solution of 10mL toluene, 5.0mL ethanol, 1.0mL water, Under the protection of nitrogen, microwave reflux reaction for 4 hours; after the reaction solution was cooled, separate the liquids, extract with dichloromethane, combine the organic phases, wash with saturated brine and dry with magnesium sulfate to remove water; remove the solvent with a rotary evaporator to obtain a solid powder, and then use pure petroleum ether as eluent to carry out column separation to obtain a light yellow solid powder, which is recrystallized in petroleum ether to obtain a light yellow block crystal.

Embodiment 3

[0025] Weigh 5,5-dibromo-2,2-dithiophene (0.162g0.5mmol), 3,4,5-trifluorophenylboronic acid (0.211g1.2mmol), tetrakis(triphenylphosphine)palladium (0.0246g0 .03mmol), potassium carbonate (0.828g6.0mmol) was mixed in a 100mL reaction device, and the reaction device was vacuumized and filled with nitrogen, and the operation was repeated three times, and then a mixed mixture of 16mL toluene, 8mL ethanol, and 1.6mL water was added. Liquid, microwave reflux reaction under the protection of nitrogen for 3 hours; after the reaction solution is cooled, separate the liquids, extract with dichloromethane, combine the organic phases, wash with saturated brine and dry with magnesium sulfate to remove water; use a rotary evaporator to remove the solvent, A solid powder was obtained, and then purified petroleum ether was used as an eluent for column separation to obtain a light yellow solid powder, which was recrystallized in petroleum ether to obtain a light yellow block crystal.

[0026] ...

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Abstract

The invention discloses a trifluorophenyl-containing dithiophene derivative and a preparation method thereof. The derivative has a molecular formula of C20H8F6S2, and belongs to a monoclinic crystal system, the space group is P2(1) / n, and the unit cell parameter alpha=gamma= 90-degree, and beta = 94.84-degree. The trifluorophenyl-containing dithiophene derivative has a clear spatial structure andan accurate molecular formula, and has simple synthesis steps, low cost, high yield, high thermal stability, high fluorescence emission intensity, and wide application prospects in the field of fluorescent materials.

Description

technical field [0001] The invention belongs to the field of material chemistry, and in particular relates to a trifluorophenyl-containing bisthiophene derivative and a preparation method thereof. Background technique [0002] Fluorescent materials are closely related to people's daily life, and are widely used in dyes, photooxidants, chemical and biological analysis, portable electronic devices and many other fields, and have always been the focus of people's research. Compared with inorganic materials, organic fluorescent materials have incomparable advantages, such as high nonlinear coefficient, low dielectric constant, fast response time, and low cost, and are mostly used in organic light-emitting diodes (OLEDs), organic light-emitting transistors (OLETs) , organic thin film transistors (OTFTs), photovoltaic materials (OPVs) and other light electronic devices. Chinese patent 200910112709.X introduces an organic fluorescent material of glutamic acid derivatives, which em...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/12C09K11/06
CPCC07D333/12C09K11/06C09K2211/1007C09K2211/1092
Inventor 李星崔春雨
Owner NINGBO UNIV
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