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Compounds with aggregation-induced luminescence function, preparation methods and applications thereof

A technology of aggregation-induced luminescence and compounds, applied in the field of compounds with aggregation-induced luminescence function, can solve the problems of low labeling efficiency, small Stokes shift, poor photostability, etc., to improve detection sensitivity and facilitate post-processing operation , the effect of mild reaction conditions

Active Publication Date: 2022-07-12
汉中职业技术学院
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, GFP is sensitive to proteolytic enzymes, small Stokes shift, poor photostability and other shortcomings make cell tracking can not achieve the desired effect
In addition, transfecting fluorescent proteins is time-consuming, cumbersome, inefficient labeling, and interferes with the normal function of cells, which further brings inconvenience to researchers

Method used

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  • Compounds with aggregation-induced luminescence function, preparation methods and applications thereof
  • Compounds with aggregation-induced luminescence function, preparation methods and applications thereof
  • Compounds with aggregation-induced luminescence function, preparation methods and applications thereof

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preparation example Construction

[0045] The invention provides a method for preparing an aggregation-induced luminescent compound. The 2-hydroxy-1-naphthalene carboxaldehyde and the compound of formula II are condensed to form an intermediate with a Schiff base structure of formula III; . Further and oxalyl chloride, bromomethylbenzene boronate pinacol ester, nitric acid, Br 2 Derivatization reactions give compounds of formula I. figure 1 It is the basic roadmap for the synthesis of the aggregation-induced luminescent compound prepared in the present invention. The structures of various compounds are as follows:

[0046]

[0047] II, where X=O or S.

[0048]

[0049] III, where X=O or S.

[0050]

[0051] IV, where X=O or S.

Embodiment 1

[0053] Mix 1 mmol of 2-hydroxy-1-naphthalenecarboxaldehyde and 1.05 mmol of 2-aminothiophenol in 10 mL of absolute ethanol, heat to reflux under nitrogen protection, and react for 8 to 12 hours, or monitor the progress of the reaction with a thin-layer chromatographic plate. The reaction was stopped after the reaction of the raw materials was completed. After the temperature of the reaction solution is lowered to room temperature, the intermediate of the Schiff base structure is obtained; after the intermediate is purified by recrystallization from ethanol, the pale yellow solid is collected by filtration to obtain a light yellow solid which is directly used in the next oxidation reaction, and the oxidant 2,3-dichloro-5, 6-Dicyano-p-benzoquinone (DDQ) was heated to reflux in toluene and reacted for 4 hours to obtain the crude product of compound 1 with aggregation-induced luminescence function. The obtained crude product was concentrated, passed through a silica gel chromatogr...

Embodiment 2

[0059] 1mmol 2-hydroxy-1-naphthalene carboxaldehyde and 1.05mmol 2-aminothiophenol were mixed in 10mL absolute ethanol, heated to reflux under nitrogen protection, and reacted for 8 hours. The reaction progress was monitored with a thin layer chromatography plate. After the reaction of the raw materials was completed Stop the reaction. After the temperature of the reaction solution is lowered to room temperature, the intermediate of the Schiff base structure is obtained; the intermediate is obtained by recrystallization and purification in ethanol, and the oxidant 2-iodoylbenzoic acid is heated and refluxed in toluene, and reacted for 2 hours to obtain an aggregation-induced luminescence. The crude product of functional compound 1 was concentrated, and the crude product obtained was passed through a silica gel chromatography column and eluted with ethyl acetate / n-hexane (volume ratio 1 / 15) to obtain 113 mg of compound 1 with a yield of 41%.

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Abstract

The present invention relates to a compound with aggregation-induced luminescence function. Its chemical structure is shown in general formula I. The reaction obtains a Schiff base structure intermediate; the intermediate is obtained through recrystallization and purification operation, and then reacts with an oxidant in an organic solvent to obtain a compound with aggregation-induced luminescence function. The compound is further modified to obtain a series of functionalized aggregation-induced luminescent compounds. The synthesis method of such compounds is simple, the reaction conditions are mild and easy to synthesize, the post-processing operation is convenient, the yield is high, and the heating reaction shortens the reaction time. The resulting aggregation-induced luminescent compound has an excited state intramolecular proton transfer effect. There is an intramolecular weak hydrogen bond between the hydroxyl hydrogen atom on the naphthalene ring and the nitrogen atom on the ortho-benzothiazole ring, which has an excited intramolecular proton transfer effect and exhibits a large Stokes shift.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, relates to a compound with aggregation-induced luminescence function, and also relates to a preparation method and application of the compound. Background technique [0002] Conventional fluorescent chromophores exhibit reduced fluorescence or even no light at high concentrations, a phenomenon known as the "concentration quenching" effect. The main reason for concentration quenching is related to the formation of aggregates, so the concentration quenching effect is often called "aggregation-caused quenching (ACQ)". In 2001, Professor Tang Benzhong's research group discovered a peculiar phenomenon: some silole molecules hardly emit light in solution, but the light emission is greatly enhanced in the aggregated state or solid thin film. Because this luminescence enhancement is caused by aggregation, this phenomenon is vividly defined as "aggregation-induced emission (AIE)". Compared wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/66C07D263/57C07F5/02C09K11/06G01N21/64A61P29/00A61P11/00A61P1/16A61P35/00
CPCC07D277/66C07D263/57C07F5/025C09K11/06G01N21/6402A61P29/00A61P11/00A61P1/16A61P35/00C09K2211/1011C09K2211/1033C09K2211/1037C09K2211/1096
Inventor 闫新豪吴鹏张弛李军红
Owner 汉中职业技术学院
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