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Multi-site modifiable aggregation-induced emission quinoline nitrile derivative as well as preparation method and application thereof

A technology of aggregation-induced luminescence and derivatives, which can be used in luminescent materials, organic chemistry methods, chemical instruments and methods, etc., and can solve the problems of difficult functional modification and expansion, limited application, and easy aggregation.

Pending Publication Date: 2020-11-24
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the structural characteristics of quinoline nitrile itself, its modifiable sites are in short supply, making it difficult to carry out functional modification and expansion.
At the same time, traditional aggregation-induced luminescent compounds are prone to aggregation in water, resulting in fluorescence that greatly limits their application in biological systems (Chem.Sci., 2019, 10, 398–405. Angew.Chem.Int.Ed. 12)

Method used

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  • Multi-site modifiable aggregation-induced emission quinoline nitrile derivative as well as preparation method and application thereof
  • Multi-site modifiable aggregation-induced emission quinoline nitrile derivative as well as preparation method and application thereof
  • Multi-site modifiable aggregation-induced emission quinoline nitrile derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] (1) Synthesis of Dye I-1:

[0028]

[0029] Add bromomethylquinoline (1g, 4.5mmol), iodoethanol (1.42g, 8.3mmol), ethanol (20mL) into a 50mL single-necked flask, heat at 60°C for 24h under nitrogen protection, cool to room temperature, and rotate to evaporate under reduced pressure , a black-green solid (1.6 g, 4.0 mmol) was obtained, yield: 89.9%, which was directly used in the next reaction.

[0030]

[0031] In a 50mL single-necked flask, the product of the previous step (1.6g, 4.0mmol), malononitrile (0.528g, 8.0mmol), sodium ethoxide (0.54g, 8.0mmol) and ethanol (20mL), heated at 60°C for 20h under nitrogen protection, and cooled After reaching room temperature, the solvent was removed by rotary evaporation under reduced pressure, and the product (0.4 g, 1.2 mmol) was separated by column chromatography. Yield: 30%.

[0032] 1 H-NMR (400MHz, DMSO-d 6 , ppm): δ9.0 (S, 1H, Ar-H), 8.0 (d, J=4.4Hz, 1H, Ar-H), 6.8 (S, 1H, Ar-H), 5.0 (S, 1H, OH), 4.5(S, 2H, CH ...

Embodiment 2

[0061] Absorption and Fluorescence Spectrum of Dye I-3 in Ethanol Water System

[0062] The dye I-3 prepared in Example 1 was dissolved in analytically pure dimethyl sulfoxide to make 1.0 × 10 -3 stock solution of M. Then prepare 2970 μL of mixed solvents of ethanol (EtOH) / water in different proportions. Take 30 μL of the above stock solution and add it to the prepared EtOH / water mixed solvent in different proportions, mix well and transfer to an optical quartz cuvette (10×10mm) to test its absorption and fluorescence spectra. Such as Figure 4-6 As shown, the dye I-3 exhibits a broad absorption peak at 400-550nm, and the maximum absorption wavelength is located at 450nm; with 450nm as the excitation wavelength, the maximum emission peak of the dye I-7 is approximately located at 720nm, located in the near-infrared region. The Stokes shift reaches 270nm; and the dye I-3 has no fluorescence in pure water and has the potential of biological application, and its fluorescence i...

Embodiment 3

[0064] Dye I-3 for fluorescent labeling of bovine serum albumin (BSA)

[0065] In order to study the response of dye I-3 to BSA, we first prepared 2970 μL of different concentrations of BSA (0, 40, 80, 120, 160, 200, 240, 480, 800 μg / mL) in PBS (pH=7). Then add 30 μL of the stock solution in real-time example 2 to each portion, mix well and quickly transfer to an optical cuvette to measure its absorption and fluorescence spectra. Such as Figure 7-9 As shown, as the concentration of BSA increases, the absorption spectrum gradually broadens, and the fluorescence intensity increases gradually, and the fluorescence enhancement at 720nm has a very good linear relationship (R 2 = 0.996).

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Abstract

The invention belongs to the technical field of fine chemical engineering, and particularly relates to a multi-site modifiable aggregation-induced emission quinoline nitrile derivative as well as a preparation method and application thereof. The structure of the derivative is as shown in formula I. In the formula I, R1 is any one of N,N-dimethyl-4-(thiophene-2-yl) aniline or N,N-diphenyl-4-(thiophene-2-yl) aniline; R2 is any one of hydroxyl, halogen, dimethylamino, trimethylamine or carboxyl; and R3 is any one of halogen, dimethylamino, trimethylamino, N,N-xylylamine, triphenylamine, pyridine,carboxyl or aldehyde group. The derivative provided by the invention can be used for in-vitro real-time rapid detection of serum protein content.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, and specifically relates to the introduction of different substituents at the end of the quinoline nitrile nitrogen ethyl group and the 6-position of quinoline nitrile to increase the modifiable sites of the quinoline nitrile parent, and to construct a water-soluble fluorescent probe to realize the detection of serum protein Real-time, fast, linear response. Background technique [0002] In 2001, Academician Tang Benzhong of Hong Kong University of Science and Technology discovered the aggregation-induced emission (AIE) phenomenon compound (Chem. It is widely used in various fields, especially in the field of biological imaging (Angew. Chem. Int. Ed. 2020, 59, 9812-9825). Zhu Weihong's research group obtained a new AIE parent quinoline nitrile (QM) by rationally designing the oxygen atom of the traditional benzopyranonitrile into a nitrogen ethyl group (ACS Appl.Mater.Interfaces 2013,5,19...

Claims

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Application Information

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IPC IPC(8): C07D215/18C07D409/06C07D215/38C07D215/12C09K11/06C09B57/00G01N21/64
CPCC07D215/18C07D409/06C07D215/38C07D215/12C09K11/06C09B57/00G01N21/6428C09K2211/1014C09K2211/1029C09K2211/1092C07B2200/13
Inventor 朱为宏朱志荣王琪刘明张有恒刘振兴李翔宇赵晓蕾
Owner EAST CHINA UNIV OF SCI & TECH
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