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A kind of bromopyridine bisthiophene purple-blue fluorescent material

A technology of bromopyridine dithiophene and blue fluorescence, which is applied in the field of luminescent materials, can solve the problems of harsh preparation conditions, expensive preparation, and cumbersome synthesis steps, and achieve the effects of simple synthesis steps, high luminous efficiency, and mild reaction conditions

Active Publication Date: 2020-03-13
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

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Take 5,5'-dibromo-2,2'-dithiophene (0.325g 1.0mmol), 3-pyridineboronic acid (0.246g 2.0mmol), tetrakis(triphenylphosphine)palladium (0.035g 0.03mmol) and carbonic acid Potassium (1.106g 8.0mmol) was mixed in a 100mL reaction device. After the reaction device was vacuumed, nitrogen gas was passed. Repeat the operation three times, and then add a mixed solution of 18 mL of toluene, 9 mL of ethanol, and 3 mL of water. The reaction was refluxed for 2 days. After the reaction was completed, the liquids were cooled and separated, extracted with dichloromethane, the organic phases were combined, washed with saturated brine and dried over magnesium sulfate to remove water. The solvent was removed by a rotary evaporator to obtain a solid powder, which was then separated through a column with an eluent of petroleum ether: ethyl acetate = 1:1 (volume ratio) to obtain a light yellow solid powder.

Embodiment 2

[0029] Take 5,5'-dibromo-2,2'-dithiophene (0.325g 1.0mmol), 3-pyridineboronic acid (0.271g 2.2mmol), tetrakis(triphenylphosphine) palladium (0.046g 0.04mmol) and carbonic acid Potassium (1.383g 10.0mmol) was mixed in a 100mL reaction device. The reaction device was evacuated and nitrogen was passed through. Repeat the operation three times, then add a mixed solution of 30 mL of toluene, 15 mL of ethanol, and 5 mL of water. The reaction was refluxed for 2 days. After the reaction was completed, the liquids were cooled and separated, extracted with dichloromethane, the organic phases were combined, washed with saturated brine and dried over magnesium sulfate to remove water. The solvent was removed by a rotary evaporator to obtain a solid powder, which was then separated through a column with an eluent of petroleum ether: ethyl acetate = 1:1 (volume ratio) to obtain a light yellow solid powder.

Embodiment 3

[0031] Take 5,5'-dibromo-2,2'-dithiophene (0.650g 2.0mmol), 3-pyridineboronic acid (0.738g 6.0mmol), tetrakis(triphenylphosphine)palladium (0.116g 0.1mmol) and carbonic acid Potassium (3.870g 28.0mmol) was mixed in a 100mL reaction device. The reaction device was evacuated and nitrogen gas was passed. Repeat the operation three times, and then add a mixture of toluene 36mL, ethanol 18mL, and water 6mL. Reflux reaction for 3 days. After the reaction was completed, the liquids were cooled and separated, extracted with dichloromethane, the organic phases were combined, washed with saturated brine and dried over magnesium sulfate to remove water. The solvent was removed by a rotary evaporator to obtain a solid powder, which was then separated through a column with an eluent of petroleum ether: ethyl acetate = 1:1 (volume ratio) to obtain a light yellow solid powder.

[0032] The substances participating in the reaction in the above examples are all chemically pure and above grade...

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Abstract

The invention discloses a bromopyridine dithiophene purple-blue fluorescent material. The fluorescent material is a unilaterally coupled pyridine dithiophene organic compound named as 3-(5'-bromo-[2,2'-bisthiophene]-5-yl)pyridine, the molecular formula of the fluorescent material is C13H8NS2Br, the crystal system is orthogonal, and the space group is Pbca, a is equal to 14.6864 angstroms, b is equal to 6.0096 angstroms, and c is equal to 27.7452 angstroms. The fluorescent material has a definite space structure and an accurate molecular formula, synthesis steps are simple, and reaction conditions are mild. By unilaterally introducing a pyridine group to a site 5 of dithiophene, the electronic conjugated delocalization range of the material is increased, the luminescence property of the material is improved, and the stability and dissolubility of the material are improved; and the material has potential application prospects as the fluorescent material.

Description

technical field [0001] The invention belongs to the technical field of luminescent materials, in particular to a bromopyridine bisthiophene organic luminescent material. Background technique [0002] Fluorescent materials are closely related to human daily life, and are widely used in dyes, photooxidants, optical brighteners, chemical and biological analysis and many other fields. Fluorescent chemical sensors and molecular signaling systems developed in recent years have greatly expanded the application of fluorescent materials, which have broad application prospects in pharmacy, physiology, environmental science, and information science and technology. The current research on organic luminescent materials is attracting more and more people's interest. [0003] In the 1960s, Pope et al. discovered the electroluminescence phenomenon of organic semiconductor materials, but because single crystal anthracene was used as the light-emitting layer, the device driving voltage was h...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/14C09K11/06
CPCC07D409/14C09K11/06C09K2211/1029C09K2211/1092
Inventor 崔春雨李星
Owner NINGBO UNIV
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