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Benzothiazole-benzyl cyanide compound and preparation method and application thereof

A technology of benzothiazole and phenethyl cyanide, applied in chemical instruments and methods, organic chemistry, fluorescence/phosphorescence, etc., can solve the problems of short fluorescence emission wavelength, difficult synthesis, small Stokes shift, etc., and achieve convenient purification. , broad application prospects, the effect of large Stokes displacement

Active Publication Date: 2019-12-20
HENGYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problems such as small Stokes shift in existing AIE compounds, short fluorescence emission wavelength (concentrated in ultraviolet light and visible light region), and difficult synthesis, the present invention provides A benzothiazole-phenacetin compound with both excited-state intramolecular proton transfer and aggregation-induced luminescence properties, its preparation method and application, the method has high fluorescence quantum yield, large Stokes shift, optical The stable and yellow-emitting 2-(2'-hydroxy-3'-aldehyde-5'-methylphenyl)benzothiazole (abbreviated as BA) is the ESIPT structural module, which has electron-withdrawing properties through Knoevenagel condensation reaction The AIE structural module 4-cyanophenylacetonitrile is bonded to obtain a near-infrared fluorescent compound (BA-CN for short) with both excited-state intramolecular proton transfer and aggregation-induced luminescence properties.

Method used

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  • Benzothiazole-benzyl cyanide compound and preparation method and application thereof
  • Benzothiazole-benzyl cyanide compound and preparation method and application thereof
  • Benzothiazole-benzyl cyanide compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Take a clean round bottom flask, add 1 mmol of BA, 71.1 mg of 4-cyanophenylacetonitrile, 100 μl of triethylamine and 25 ml of acetonitrile in sequence, and stir at 82°C for 12 hours. After the reaction was finished, a brown precipitate was precipitated, and TLC plate was spotted, and it was found that most of the raw material BA was unreacted. The precipitate was filtered and washed 2-3 times with acetonitrile to obtain pure BA-CN (yield 41.6%).

Embodiment 2

[0045] Take a clean round bottom flask, add 1 mmol BA, 142.2 mg 4-cyanophenylacetonitrile, 100 μl triethylamine and 25 ml acetonitrile in sequence, and stir at 82°C for 12 hours. After the reaction was finished, a brown precipitate precipitated out, and TLC spotting showed that the raw material BA was almost completely reacted. The precipitate was filtered and washed 2-3 times with acetonitrile to obtain pure BA-CN (yield 86.2%).

Embodiment 3

[0047] Take a clean round bottom flask, add 1 mmol of BA, 284.3 mg of 4-cyanophenylacetonitrile, 100 μl of triethylamine and 25 ml of acetonitrile in sequence, and stir at 82°C for 12 hours. After the reaction was finished, a brown precipitate precipitated out, and TLC spotting showed that the reaction of raw material BA was complete, and a large amount of 4-cyanophenylacetonitrile remained. The precipitate was filtered, washed with acetonitrile for 2-3 times, and then separated by column chromatography to obtain pure BA-CN (71.6% yield).

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Abstract

The invention provides a benzothiazole-benzyl cyanide compound, wherein the molecular formula is as follows. The compound has both excited state intramolecular proton transfer and aggregation inducedluminescence properties. The invention also provides a preparation method of the compound, which has the characteristics of simple synthesis, only one step reaction, mild reaction conditions, high yield reaching more than 80%, large Stokes shift reaching 330nm, emission wavelength 635nm in near infrared region and the like. The compound can be applied to the field of fluorescence detection.

Description

technical field [0001] The invention relates to the technical field of preparation of organic functional materials, and relates to a benzothiazole-phenacetin compound, a preparation method and an application. Background technique [0002] The discovery of aggregation-induced emission (AIE) compounds effectively overcomes the concentration-induced quenching effect brought about by traditional fluorescent molecules, and also brings opportunities for the application and development of fluorescent materials. In the fields of chemical / biological detection and biological imaging, AIE compounds have advantages that other compounds cannot match: (1) have high efficiency of aggregation state luminescence, which can improve the sensitivity of biological detection; (2) have good cell permeability and cell Compatibility, which is beneficial to cell imaging applications; (3) has excellent photobleaching resistance, and is suitable for long-term tracking of intracellular target substances...

Claims

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Application Information

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IPC IPC(8): C07D277/66C09K11/06G01N21/64
CPCC07D277/66C09K11/06G01N21/6428C09K2211/1037C09K2211/1007
Inventor 谷标唐斯萍刘梦琴易英杰
Owner HENGYANG NORMAL UNIV
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