Schiff base compound based on tetraphenylethylene and mandelonitrile as well as preparation method and application of Schiff base compound

A technology of tetraphenylethylene and tetraphenylethylene, which is applied in the field of analysis and detection, and can solve the problems of low fluorescence efficiency and inability to realize the application of red fluorescent probes.

Active Publication Date: 2017-03-08
HKUST SHENZHEN RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The object of the present invention is to provide a kind of Schiff base compound based on tetraphenylethylene and maleonitrile and its preparation method and application, solve the Schiff base compound based on tetraphenylethylene and maleonitrile in the prior art The fluorescence efficiency is low and cannot be applied as a red fluorescent probe

Method used

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  • Schiff base compound based on tetraphenylethylene and mandelonitrile as well as preparation method and application of Schiff base compound
  • Schiff base compound based on tetraphenylethylene and mandelonitrile as well as preparation method and application of Schiff base compound
  • Schiff base compound based on tetraphenylethylene and mandelonitrile as well as preparation method and application of Schiff base compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Embodiment 1: two tetraphenylethylene maleonitrile synthesis (TPE-DMNS)

[0079]

[0080] Reflux 1g of tetrastyryl salicylaldehyde and appropriate amount of diaminomaleonitrile hydrazine hydrate under 25ml for 4h (adding acetic acid as catalyst), after cooling, remove ethanol under reduced pressure and then extract. After the organic phase is dried, it is separated by a column to obtain light yellow 0.8g of green solid, namely TPE-DMNS structure. MALDI-TOF (m / z): [M+]calcd.C 58 h 40 N 4 o 2 , 824.3151; found, 824.4532. Anal Calc. for C 20 h 14 N 2 O: C, 84.44; H, 4.89; N, 6.79; O, 3.88. Found: C, 84.64; H, 4.84; N, 6.74; O, 3.86.

Embodiment 2

[0081] Example 2: ESIPT (intramolecular proton transfer) properties of TPE-DMNS

[0082] Such as figure 1 Shown is the fluorescence spectrum of TPE-DMNS under different polarities. With the change of polarity, the ratio of alcohol emission (near 432nm) and ketone emission (near 615nm) of TPE-DMNS changes significantly, which is typical ESIPT launch.

Embodiment 3

[0083] Example 3: Research on Aggregation-Induced Luminescence (AIE) Properties of TPE-DMNS

[0084] For ESIPT molecules, the aggregation state is mostly ketone emission, so the aggregation luminescence phenomenon at this place was detected. Such as Figure 2A and 2B As shown, a certain proportion of water is continuously added to the tetrahydrofuran solvent of TPE-DMNS (dissolved single molecular state), and TPE-DMNS slowly aggregates into nanoparticles due to solubility problems, and the fluorescence intensity of the alcohol form gradually decreases, and the intensity of the ketone form increases. The proportion of those increases with the increase of water content, indicating that TPE-DMNS has AIE properties. Compared with the Salen-type Schiff base structure of other types of maleonitrile, TPE-DMNS exhibits ESIPT and AIE properties and has the potential of a fluorescent probe.

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Abstract

The invention relates to a Schiff base compound based on tetraphenylethylene and mandelonitrile as well as a preparation method and an application of the Schiff base compound. Compared with common Salen type mandelonitrile fluorescent probe structures, probe structures in the type have excellent red fluorescent behaviors and excellent solid state (state of aggregation) efficiency, realize selective recognition and imaging of specific structures in cells, have better responsiveness to anions, cations and pH values, thereby having extremely broad application prospect in the fields of biology, medical treatment, health and monitoring.

Description

technical field [0001] The invention relates to the technical field of analysis and detection, more specifically, to a Schiff base compound based on tetraphenylethylene and maleonitrile, a preparation method and application thereof. Background technique [0002] With the rapid development of the national economy and the continuous improvement of people's living standards, real-time monitoring of personal health, disease prevention and treatment have gradually become people's livelihood issues that people pay more attention to. Compared with the delay of traditional in vitro chemical testing and the harmfulness of online radiation detection, fluorescence online imaging technology has gradually entered people's field of vision with its advantages of high efficiency, greenness and strong real-time performance, and has been widely used in cellular immunology, microbiology, etc. Science, molecular biology, genetics, neurobiology, pathology, oncology, clinical laboratory science, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/30C07C253/30C07C255/61C07D295/088C07D213/04C07D333/32C07D209/88C07D213/64C07D215/233C07D217/24C07D239/36C09K11/06G01N21/64
Inventor 唐本忠王志明赵祖金秦安军李晓东侯雪
Owner HKUST SHENZHEN RES INST
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