D-pi-A type tetraphenylethynyl phenyl substituted pyridine conjugated luminescent small molecule and synthesis method thereof

A technology of ethynylphenyl and tetraphenylethylene, applied in luminescent materials, chemical instruments and methods, organic chemistry, etc., to achieve good photophysical properties, good thermal stability, and excellent fluorescent properties

Inactive Publication Date: 2021-10-22
SHANGRAO NORMAL UNIV +1
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  • Claims
  • Application Information

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Problems solved by technology

[0006] So far, there is no report on the construction of D-π-A type light-emitting small molecules using tetraphenylethylene (TPE) units and 2,4,6-triarylpyridine units through alkyne groups.

Method used

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  • D-pi-A type tetraphenylethynyl phenyl substituted pyridine conjugated luminescent small molecule and synthesis method thereof
  • D-pi-A type tetraphenylethynyl phenyl substituted pyridine conjugated luminescent small molecule and synthesis method thereof
  • D-pi-A type tetraphenylethynyl phenyl substituted pyridine conjugated luminescent small molecule and synthesis method thereof

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Embodiment 1

[0058] The preparation of 2,6-diaryl-4-(4-bromophenyl)pyridine (4) (synthetic methods are the same, but the raw materials are different): add 4-bromobenzaldehyde (9.95 g, 50mmol), arylacetophenone (105mmol), ammonium acetate (27.00g, 350mmol) and glacial acetic acid (40mL). Under the protection of nitrogen, react at a temperature of 110-130° C. for 7 h, and track the reaction by thin layer chromatography (TLC). After the reaction was complete, the reaction was stopped and cooled to room temperature, and a brownish-yellow viscous substance was precipitated. Suction filtration and washing with absolute ethanol for 2-3 times, the crude product was dried and recrystallized with absolute ethanol to obtain the target compound 4.

[0059] 2,6-Diphenyl-4-(4-bromophenyl)pyridine (4a): Yield: 86%; white needle-like solid, mp=131~132℃. 1 H NMR (400MHz, CDCl 3 ):δ(ppm)=8.20(d,J=8.0Hz,4H),7.83(s,2H),7.66(d,J=8.0Hz,2H),7.61(d,J=8.0Hz,2H), 7.55-7.51(m,4H),7.49-7.45(m,4H),3.88(s,6H).

[...

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Abstract

The invention discloses a D-pi-A type tetraphenylethynyl phenyl substituted pyridine conjugated luminescent small molecule and a synthesis method thereof. The preparation method comprises the following steps: carrying out Chichibabin reaction on 4-bromobenzaldehyde, aryl acetophenone and ammonium acetate under the catalysis of glacial acetic acid to obtain a 2, 6-diaryl-4-(4-bromophenyl) pyridine compound; performing a Sonogashira coupling reaction on the 2, 6-diaryl-4-(4-bromophenyl) pyridine and 1-(4-ethynyl phenyl)-1, 2, 2-triphenylethylene under the catalysis of Pd (PPh3) 2Cl2 and CuI, thereby obtaining the D-pi-A type tetraphenylethylene ethynyl phenyl substituted pyridine conjugated luminescent small molecule. The small molecule is high in thermal stability, has an aggregation-induced emission (AIE) effect, relatively high fluorescence quantum yield and relatively long fluorescence lifetime, and can be applied as a photoluminescent material.

Description

technical field [0001] The invention relates to a light-emitting organic small molecule material, in particular to a D-π-A tetrastyrylethynyl phenyl-substituted pyridine conjugated light-emitting small molecule, and a synthesis method thereof, which belongs to the technical field of organic light-emitting materials. Background technique [0002] The design and synthesis of organic fluorescent compounds is a research hotspot in recent years. Such compounds can be widely used in chemical sensors, organic light-emitting diodes, liquid crystal displays, solar cells, etc. Dye sensitizers are the most important part of solar cells, so it is of great significance to study dye molecules with higher conversion efficiency. A large number of studies have shown that organic dye molecules with D-π-A structure have a higher conversion rate, because molecules with this structure can improve optical properties by changing the donor-acceptor and π-bridge. [0003] At present, a large number...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/16C07D213/26C07D213/30C09K11/06
CPCC07D213/16C07D213/26C07D213/30C09K11/06C09K2211/1029C09K2211/1007
Inventor 张小兰董洪霞周一芳潘阳盛寿日黄振钟
Owner SHANGRAO NORMAL UNIV
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