Pyrene unit-containing organic fluorescent material with aggregation-induced emission as well as preparation method and application of pyrene unit-containing organic fluorescent material

A technology of aggregation-induced luminescence and fluorescent materials, applied in the field of fluorescent inks, can solve the problems of easy oxidative decomposition loss, poor thermal stability, fluorescence quenching, etc., and achieve the effects of good biocompatibility, good thermal stability, and high color purity

Active Publication Date: 2021-06-15
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the existing problems in the above-mentioned prior art: difficult to disperse, poisonous, poor thermal stability, easy to oxidize and decompose and lose discoloration properties, fluorescence quenching occurs when the content of phosphor powder is high, High cost and other disadvantages, the primary purpose of the present invention is to provide an organic fluorescent material with aggregation-induced luminescent pyrene-containing units, which has excellent optical properties and biological non-toxicity

Method used

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  • Pyrene unit-containing organic fluorescent material with aggregation-induced emission as well as preparation method and application of pyrene unit-containing organic fluorescent material
  • Pyrene unit-containing organic fluorescent material with aggregation-induced emission as well as preparation method and application of pyrene unit-containing organic fluorescent material
  • Pyrene unit-containing organic fluorescent material with aggregation-induced emission as well as preparation method and application of pyrene unit-containing organic fluorescent material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] The preparation of embodiment 1 carbazole biphenylacetonitrile

[0052] Under the condition of nitrogen protection, add p-benzocarbazole borate and p-bromophenylacetonitrile (molar ratio is 1: (1~3)), potassium carbonate, tetrakis (triphenylphosphine) palladium into the double-necked flask, Then add 10-20mL of toluene, ethanol and water, stir vigorously, keep the temperature at 90°C, reflux for 24h, cool to room temperature, extract, wash and filter to obtain the primary product, separate by chromatography column or recrystallize to obtain carbazole biphenyl Acetonitrile, its molecular structure is shown in 1a in formula (1), its synthetic route is shown in formula (1), and its productive rate is about 61%.

[0053]

Embodiment 2

[0054] Example 2 Preparation of 2-(4'-(9H-carbazole)-[4-(1,1'-biphenyl)]-3-(1-pyrenyl)acrylonitrile (Py-2Ph-Cz)

[0055] Under the condition of nitrogen protection, the carbazole biphenylacetonitrile and 1-pyrene formaldehyde and potassium tert-butoxide prepared in Example 1 are added in the double-necked bottle (the molar ratio is 1: (1~3): 3), and then Add 10-20mL of absolute ethanol, stir vigorously, keep the temperature at 90°C, reflux for 24h, cool to room temperature, wash with ethanol and suction filter to obtain the initial product, and further recrystallize in a mixed solvent of dichloromethane and n-hexane to obtain 2- (4'-(9H-carbazole)-[4-(1,1'-biphenyl)]-3-(1-pyrenyl)acrylonitrile (Py-2Ph-Cz), its molecular structure is as follows: As shown in 2a in 2), its synthetic route is shown in formula (2), and its yield is about 74%.

[0056]

[0057] figure 1 Obtain the Py-2Ph-Cz for embodiment 2 1 H NMR chart. figure 2 The 13CNMR pattern of Py-2Ph-Cz was obtained...

Embodiment 3

[0058] Example 3 Preparation of 1-(4-benzaldehyde)pyrene

[0059] Under the condition of nitrogen protection, add 1-bromopyrene and 4-formylphenylboronic acid (the molar ratio is 1:(1~3)), potassium carbonate, tetrakis-(triphenylphosphine)-palladium into the double-necked flask , then add 10-20mL of toluene, ethanol and water, stir vigorously, keep the temperature at 90°C, reflux for 24h, cool to room temperature, extract, wash and filter to obtain a crude product, separate by chromatography column or recrystallize to obtain 1-(4 -benzaldehyde group)pyrene, its molecular structure is shown in 3a in formula (3), its synthetic route is shown in formula (3), and its yield is about 51%.

[0060]

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Abstract

The invention belongs to the field of fluorescent ink, and discloses a pyrene unit-containing organic fluorescent material with aggregation-induced emission as well as a preparation method and application of the pyrene unit-containing organic fluorescent material. The molecular structural formula of the organic fluorescent material is as shown in the specification, wherein the substitution position of a substituent group is at the 1-site or 2-site of a pyrene unit, the substituent group R1 or R2 is cyano, R3 substituent is selected from substituted aromatic hydrocarbon containing 5-30 carbon atoms, aryloxy containing 6-50 ring atoms, aromatic amine containing 5-30 carbon atoms, boron aromatic hydrocarbon containing 6-20 carbon atoms or aromatic heterocyclic group containing 5-40 carbon atoms, and m is more than or equal to 0 and less than or equal to 10. The organic fluorescent material provided by the invention has typical aggregation-induced emission properties, can realize printing of clear anti-counterfeiting patterns on different substrates, and is expected to be directly applied to the anti-counterfeiting field.

Description

technical field [0001] The invention belongs to the technical field of fluorescent inks, and in particular relates to an organic fluorescent material with aggregation-induced luminescent pyrene-containing units, a preparation method and application thereof. Background technique [0002] Fluorescent ink, also known as leuco ink, is a special ink that can emit fluorescence under ultraviolet light. It is widely used in the field of anti-counterfeiting because of its simple implementation, good concealment, rich colors, convenient inspection, and strong reproducibility. . Fluorescent ink is made by adding corresponding fluorescent pigments to the ink. According to different molecular structures, it can be divided into inorganic fluorescent pigments, organic fluorescent pigments and inorganic / organic composite fluorescent pigments. Inorganic fluorescent pigments are composed of metal sulfides and trace active agents, and are calcined. They have good stability and low cost, but t...

Claims

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Application Information

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IPC IPC(8): C07D209/86C07C255/34C07C253/30C09K11/06C09D11/102C09D11/107C09D11/108C09D11/50
CPCC07D209/86C07C255/34C09K11/06C09D11/102C09D11/107C09D11/108C09D11/50C09K2211/1011C09K2211/1007C09K2211/1029
Inventor 冯星王晓慧刘一苇杨晨艺欧妙宁
Owner GUANGDONG UNIV OF TECH
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