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Coumarin-based red light aggregation-induced emission material and preparation method thereof

A technology for aggregation-induced luminescence and luminescence materials, applied in the field of red light aggregation-induced luminescence materials and their preparation, can solve problems such as damage and short luminescence wavelength, and achieve the effects of easy availability of raw materials, simple and easy synthesis, and avoidance of fluorescence quenching

Inactive Publication Date: 2021-08-20
DALIAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a blue-light material with excellent photochemical and photophysical properties, triphenylamine has been widely used in electroluminescent materials and fluorescent sensors. This type of molecule is easy to synthesize, the raw materials are easy to obtain, and single bond rotation is easy to occur in the molecule. The intramolecular torsion is similar, but the aggregation-induced luminescence materials based on triphenylamine are far behind the rapid development of tetraphenylethylene-based AIE molecules
[0004] Coumarin derivatives have always been a class of fluorophores favored by researchers with excellent luminescent properties, but their luminescent wavelengths are relatively short, and they are easy to cause damage when used in vivo

Method used

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  • Coumarin-based red light aggregation-induced emission material and preparation method thereof
  • Coumarin-based red light aggregation-induced emission material and preparation method thereof
  • Coumarin-based red light aggregation-induced emission material and preparation method thereof

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Embodiment 1

[0033]

[0034] Synthesis of G-1: 4-diethylamino salicylaldehyde (1.2g, 6.3mmol), ethyl acetoacetate (1.2g, 9mmol) and piperidine (0.5mL) were mixed in 15mL absolute ethanol, reflux Heated for about 2 hours, and the end point of the reaction was determined by thin-layer chromatography. After the reaction of the raw materials was complete, it was cooled to room temperature. Filtration under reduced pressure yielded 1.42 g of yellow crystalline solid G-1 with a yield of 97%. The crude product was directly used for the next reaction without further purification.

Embodiment 2

[0036]

[0037] Synthesis of CRTP: Take compound G-1 (100mg, 0.386mmol) and 4-(diphenylamine) benzaldehyde in a round bottom flask, add piperidine (0.2ml) in absolute ethanol (molecular sieve drying) and stir at room temperature After 30 minutes, it was heated to 65° C. to continue the stirring reaction. A large amount of solids were precipitated from the reaction solution. After the end point of the reaction was determined by thin-layer chromatography, the temperature was lowered to room temperature, filtered under reduced pressure, and the filter cake was washed with a small amount of ethanol several times to obtain 60 mg of a red solid product. rate 30%. 1 HNMR (500MHz, CDCl 3 )δ8.55(s,1H),8.01(d,J=15.6Hz,1H),7.80(d,J=15.6Hz,1H),7.53(d,J=8.6Hz,2H),7.42(d, J=9.0Hz, 1H), 7.29(t, J=7.9Hz, 4H), 7.14(d, J=7.6Hz, 4H), 7.09(t, J=7.4Hz, 2H), 7.01(d, J= 8.6Hz, 2H), 6.63(dd, J=8.9, 2.2Hz, 1H), 6.49(d, J=1.9Hz, 1H), 3.46(q, J=7.1Hz, 4H), 1.25(t, J= 7.1Hz,6H). 13 C NMR(CDCl3,125...

Embodiment 5A

[0042] The picture of embodiment 5AIE fluorescent material CRTP

[0043] Take by weighing the red light AIE material CRTP in embodiment 2 and be mixed with 10 in different acetonitrile and water proportioning solution -5 μm solution, such as Figure 9 and Figure 10 As shown, when the compound CRTP is excited with a 345nm ultraviolet lamp, it can be seen that the fluorescence of the compound CRTP is very weak when the water content is 0-70%, but when the water content reaches 80%, the fluorescence is obviously enhanced, which shows that The compound CRTP has obvious aggregation-induced luminescent properties. When observed in daylight, it can be seen that the compound presents an obvious yellow color, but when the water content reaches 80%, it can be seen that the yellow color becomes weaker, which is consistent with the weaker absorption intensity observed in the ultraviolet absorption spectrum. Such as Figure 11 As shown, the fluorescence picture of solid CRTP under the...

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Abstract

The invention discloses a coumarin-based red light aggregation-induced emission material and a preparation method thereof, and belongs to the technical field of organic chemistry and material chemistry. The structural formula of the luminescent material for solving the technical problem is shown in the specification and named CRTP. The synthesis of the CRTP comprises the following steps: firstly, mixing 4-(diethylamino)salicylaldehyde, ethyl acetoacetate and piperidine in absolute ethyl alcohol, conducting refluxing and heating to obtain a G-1 product, and then further catalyzing the compound G-1 and 4-(diphenylamine) benzaldehyde with equal amount of substance under the action of piperidine to obtain a final product. The red light aggregation-induced emission material CRTP is prepared from coumarin and triphenylamine. Raw materials are easily available, and synthesis is simple and feasible. When the CRTP is gathered in a poor solvent or a water phase, the CRTP can realize obvious red light emission, the aggregation-induced quenching phenomenon of a traditional organic fluorophore can be effectively avoided, and the CRTP is expected to be applied to high-sensitivity fluorescence detection in a solid luminescent material and a living body.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and material chemistry, and specifically relates to a coumarin-based red light aggregation-induced luminescence material and a preparation method thereof. Background technique [0002] The aggregation-induced fluorescence quenching properties of traditional organic fluorescent molecules severely limit their application range as fluorescent sensors and greatly reduce their detection sensitivity. In order to improve its application, a series of new fluorescent molecules with aggregation-induced emission (AIE) properties developed by Tang Benzhong's research group in the past 20 years have attracted much attention. Such molecules are widely used in the fields of biochemical sensors, fluorescent imaging and organic light-emitting materials have a wide range of applications. [0003] The currently developed aggregation-induced luminescence materials are mainly tetraphenylethylene molecules (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C09K11/06
CPCC07D311/16C09K11/06C09K2211/1014C09K2211/1088
Inventor 张晓琳乔威威李建军谭景中汪彬
Owner DALIAN UNIV
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