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Bipyridine bisthiophene blue fluorescent material

A technology of bispyridine bisthiophene and pyridine bisthiophene, which is applied in the field of bispyridine bisthiophene organic light-emitting materials, can solve the problems of harsh preparation conditions, cumbersome synthesis steps, and expensive preparation, and achieve large delocalization, simple synthesis steps, The effect of high luminous efficiency

Active Publication Date: 2018-11-06
NINGBO UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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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  • Bipyridine bisthiophene blue fluorescent material
  • Bipyridine bisthiophene blue fluorescent material
  • Bipyridine bisthiophene blue fluorescent material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Take 5,5'-dibromo-2,2'-dithiophene (0.325g 1.0mmol), 3-pyridineboronic acid (0.271g 2.2mmol), tetrakistriphenylphosphine palladium (0.058g 0.03mmol) and potassium carbonate ( 1.658g 12mmol) was mixed in a 100mL reaction device, and the reaction device was evacuated and nitrogen was passed through, and the operation was repeated three times, then a mixed solution of toluene 18mL, ethanol 9mL, and water 3mL was added, and the reaction was refluxed at 85°C under the protection of nitrogen gas. sky. 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

[0022] Take 5,5'-dibromo-2,2'-dithiophene (0.325g 1.0mmol), 3-pyridineboronic acid (0.307g 2.5mmol), tetrakistriphenylphosphine palladium (0.046g 0.04mmol) and potassium carbonate ( 1.935g 14.0mmol) was mixed in a 100mL reaction device, and the reaction device was vacuumed and nitrogen was passed through, and the operation was repeated three times, then a mixture of toluene 30mL, ethanol 15mL, and water 5mL was added, and the reaction was refluxed at 85°C under the protection of nitrogen. 2.5 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

[0024]Take 5,5'-dibromo-2,2'-dithiophene (0.650g 2.0mmol), 3-pyridineboronic acid (0.738g 6.0mmol), tetrakistriphenylphosphine palladium (0.116g 0.1mmol) and potassium carbonate ( 2.764g 20mmol) was mixed in a 100mL reaction device. After the reaction device was vacuumed, nitrogen gas was passed, and the operation was repeated three times. Then, a mixed solution of 36 mL of toluene, 18 mL of ethanol, and 6 mL of water was added, and the reaction was refluxed at 85 ° C under the protection of nitrogen gas. sky. 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.

[0025] The substances participa...

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Abstract

The invention discloses a bipyridine bisthiophene blue fluorescent material. The fluorescent material is a bisthiophene organic compound bilaterally coupled with pyridine, and is named as 5,5'-bis(pyridine-3-yl)-2,2'-bisthiophene, the molecular formula is C18H12N2S2, the crystal system is monoclinic, the space group is P2(1) / n, and the unit cell parameters of the compound are as follows: a = 1.09994 nm, b = 0.57419 nm, c = 1.17721, alpha = gamma = 90 DEG, and beta = 103.20 DEG. The blue fluorescent material has the advantages of clear spatial structure, accurate molecular formula, simple synthesis steps, mild reaction conditions, realization of increase of the electron delocalization degree, enhancement of the luminescence performance and improvement of the stability and the solubility byintroducing pyridyl groups to the 5-positions of two sides of the bithiophene, and potential application prospect as a fluorescent material.

Description

technical field [0001] The invention belongs to the field of organic luminescent materials, in particular to a bispyridine bisthiophene organic luminescent material. Background technique [0002] Organic photoelectric materials are a special class of organic materials, which are small organic molecules and polymers with photoelectric activity containing large π conjugated bonds. Compared with inorganic optoelectronic materials, organic optoelectronic functional materials have more diversified structural composition and wider space for performance adjustment. People can obtain new materials with new structures and excellent properties through molecular design, and because of their low material density and easy structure modification. And other characteristics, it can be used for large-area preparation and flexible device preparation. With the rapid development of current optical information technology and optoelectronic industry, the demand for organic optoelectronic functio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00C09K11/06
CPCC08G83/008C09K11/06C09K2211/1458C09K2211/1466
Inventor 崔春雨李星
Owner NINGBO UNIV
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