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Aggregation-induced emission material based on thieno[3,4-b]thiophene as well as preparation method and application thereof

An aggregation-induced luminescence and 4-b technology, which is applied in the field of aggregation-induced luminescence materials and preparations based on thieno[3,4-b]thiophene, can solve problems such as low absorption rate, destruction of conjugation, and decrease in fluorescence brightness. Achieve the effects of simple reaction operation, low background fluorescence interference, and good water solubility

Active Publication Date: 2021-07-20
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although AIE molecules can significantly improve the imaging capabilities of molecules, the inherent twisted structure disrupts conjugation, resulting in lower absorption
In addition, due to the lower energy band gap, the fluorescence brightness of near-infrared organic molecules decreases with the increase of emission wavelength.

Method used

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  • Aggregation-induced emission material based on thieno[3,4-b]thiophene as well as preparation method and application thereof
  • Aggregation-induced emission material based on thieno[3,4-b]thiophene as well as preparation method and application thereof
  • Aggregation-induced emission material based on thieno[3,4-b]thiophene as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] An aggregation-induced luminescent material based on thieno[3,4-b]thiophene, which uses triphenylamine and thieno[3,4-b]thiophene as core units, and its structural formula is:

[0035]

[0036] A method for preparing the above-mentioned aggregation-induced luminescent material based on thieno[3,4-b]thiophene, comprising the following steps:

[0037] Step 1, 4-methoxy-N-(4-methoxybenzene)-N-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborin Fyl)phenyl)aniline (compound 1) (240mg, 0.55mmol) and 4-bromo-6-formylthieno[3,4-b]thiophene-2-ethyl carboxylate (compound 2) (150mg, 0.47mmol) was dissolved in 10mL of dry 1,4-dioxane, and Cs was added successively under the condition of nitrogen protection 2 CO 3 (456mg, 1.39mmol), bis(triphenylphosphine)palladium dichloride (20mg, 0.025mmol), heated to reflux at 90°C for 15h, after the reaction was completed, the reaction was cooled to room temperature. Quench the reaction with 2mol / L potassium fluoride solution of 3mL, extract with d...

Embodiment 2

[0042] A method for preparing the above-mentioned aggregation-induced luminescent material based on thieno[3,4-b]thiophene, comprising the following steps:

[0043] Step 1, 4-methoxy-N-(4-methoxybenzene)-N-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborin Fyl)phenyl)aniline (compound 1) (240mg, 0.55mmol) and 4-bromo-6-formylthieno[3,4-b]thiophene-2-ethyl carboxylate (compound 2) (150mg, 0.47mmol) was dissolved in 10mL of dry 1,4-dioxane, and Cs was added successively under the condition of nitrogen protection 2 CO 3 (308.37mg, 0.94mmol), bis(triphenylphosphine)palladium dichloride (3.3mg, 0.004mmol), heated under reflux at 100°C for 18h, after the reaction was completed, the reaction was cooled to room temperature. Quench the reaction with 2mol / L potassium fluoride solution of 3mL, extract with dichloromethane and water after the solvent is removed, collect the organic phase and dry with anhydrous sodium sulfate, remove the organic solvent under reduced pressure, the crude product c...

Embodiment 3

[0048] A method for preparing the above-mentioned aggregation-induced luminescent material based on thieno[3,4-b]thiophene, comprising the following steps:

[0049] Step 1, 4-methoxy-N-(4-methoxybenzene)-N-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborin Fyl)phenyl)aniline (compound 1) (240mg, 0.55mmol) and 4-bromo-6-formylthieno[3,4-b]thiophene-2-ethyl carboxylate (compound 2) (150mg, 0.47mmol) was dissolved in 10mL of dry 1,4-dioxane, and Cs was added successively under the condition of nitrogen protection 2 CO 3 (1541.87mg, 4.7mmol), bis(triphenylphosphine) palladium dichloride (33mg, 0.047mmol), heated to reflux at 95°C for 16h, after the reaction was completed, the reaction was cooled to room temperature. Quench the reaction with 2mol / L potassium fluoride solution of 3mL, extract with dichloromethane and water after the solvent is removed, collect the organic phase and dry with anhydrous sodium sulfate, remove the organic solvent under reduced pressure, the crude product colum...

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Abstract

The invention relates to a red light aggregation-induced emission material, in particular to an aggregation-induced emission material based on thieno[3,4-b]thiophene as well as a preparation method and application thereof. The preparation method comprises the following steps: by taking triphenylamine and thieno[3,4-b]thiophene as core units, synthesizing (E)-4-(2-(4-(4-(bis(4-methoxyphenyl)amino)phenyl)-2-(ethoxycarbonyl)thieno[3,4-b]thiophene-6-yl)vinyl)-1-methyl pyridinium iodide by using 4-(4-(bis(4-methoxyphenyl)amino)phenyl)-6-methylthieno[3,4-b]thiophene-2-carboxylic acid ethyl ester and 1,4-dimethyl pyridinium iodide; and dissolving the product into acetone, adding an aqueous solution of potassium hexafluorophosphate, and reacting to obtain the material. Fluorescence emission of the material is located in a near-infrared region, and the material is high in fluorescence brightness and can serve as a red light material to be applied to the field of imaging.

Description

technical field [0001] The invention relates to a class of red light aggregation-induced luminescence materials, in particular to an aggregation-induced luminescence material based on thieno[3,4-b]thiophene, a preparation method and application thereof. Background technique [0002] Compared with visible light, near-infrared fluorescence imaging (>650nm) has been widely used in the field of biological imaging because of its lower autofluorescence interference, less light damage, and strong penetration ability. Therefore, many near-infrared imaging materials based on quantum dots, carbon nanomaterials, and organic light-emitting materials have emerged. Organic light-emitting materials have attracted extensive attention due to their good biocompatibility, clear molecular structure, easy modification, and degradability. Therefore, it is of great significance to develop some efficient organic light-emitting materials in the fields of bioimaging. [0003] However, in practica...

Claims

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Application Information

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IPC IPC(8): C07D495/04C09K11/06G01N21/64
CPCC07D495/04C09K11/06G01N21/64C09K2211/1014C09K2211/1029C09K2211/1092
Inventor 周思荣冯丽恒
Owner SHANXI UNIV
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