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Nitrile-group-containing azulene-styrene derivatives adopted as near infrared fluorescence probe as well as preparation method and application of nitrile-group-containing azulene-styrene derivative

A technology of styrene derivatives and fluorescent probes, applied in the field of fluorescent dyes, to achieve the effect of solving the single response of the probe and simple synthesis

Inactive Publication Date: 2016-08-24
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current research and application of such compounds are mainly focused on the "aggregation-induced luminescent effect" (B.-K. An, et al. J. Am. Chem. Soc ., 2002, 124 , 14410.), and there are very few studies on its derivation to obtain smart materials that can respond to specific stimuli

Method used

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  • Nitrile-group-containing azulene-styrene derivatives adopted as near infrared fluorescence probe as well as preparation method and application of nitrile-group-containing azulene-styrene derivative
  • Nitrile-group-containing azulene-styrene derivatives adopted as near infrared fluorescence probe as well as preparation method and application of nitrile-group-containing azulene-styrene derivative
  • Nitrile-group-containing azulene-styrene derivatives adopted as near infrared fluorescence probe as well as preparation method and application of nitrile-group-containing azulene-styrene derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] (1) Synthesis of compound 3

[0049]Add 1mL of N,N-dimethylformamide to a 50mL round bottom flask, slowly add 0.1mL of phosphorus oxychloride at 0 ℃, then slowly rise to room temperature and react for 30 minutes, then add azulene (0.128 mg, 1 mmol) , react at room temperature for 1 hour, add dilute sodium hydroxide solution to adjust the pH to neutral, extract with dichloromethane three times (15mL×3), combine the organic layers, wash with saturated brine, and dry over anhydrous sodium sulfate. After vacuum concentration, separation and purification by column chromatography using petroleum ether: ethyl acetate = 10:1 (v / v) as the eluent gave dark purple oily liquid 3 with a yield of 95%. 1 H NMR (400 MHz, CDCl 3 ) δ (ppm): 10.38 (s, 1H), 9.62 (d, J = 9.6 Hz, 1H), 8.54 (d, J = 9.7 Hz, 1H), 8.30 (d, J = 4.2 Hz, 1H), 7.89 (t, J = 9.7 Hz, 2H), 7.66 (t, J = 9.9 Hz, 1H), 7.56 (t, J = 9.7 Hz, 2H), 7.36 (d, J = 4.1 Hz, 1H).

[0050] (2) Synthesis of Compound 4...

Embodiment 2

[0057] Compound I obtained above was dissolved in chloroform to form a 0.5 μmol / L solution. Add 2mL of the solution into a 1cm×1cm×4cm stoppered cuvette, then add different volumes of trifluoroacetic acid with a micro-syringe and mix evenly for 1 minute, then test its fluorescence emission spectrum, λ ex = 302 nm, the result is as figure 2 shown. With the continuous addition of trifluoroacetic acid, the fluorescence intensity of the solution gradually increased.

Embodiment 3

[0059] Compound I obtained above was dissolved in chloroform to form a 0.5 μmol / L solution. Add 2mL of the solution into a 1cm×1cm×4cm stoppered cuvette, then add a certain volume of trifluoroacetic acid with a micro-syringe and mix evenly for 1 minute, then place the solution after adding the acid under 365 nm light Under 30 minutes, test its fluorescence emission spectrum, λ ex =302 nm, with the increase of illumination time, the color of the solution will change significantly, from yellow-green to dark green, and the fluorescence intensity will also decrease obviously, the results are as follows image 3 shown.

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Abstract

The invention belongs to the technical field of fluorochrome and particularly relates to nitrile-group-containing azulene-styrene derivatives as well as a preparation method and an application of the nitrile-group-containing azulene-styrene derivatives. The nitrile-group-containing azulene-styrene derivatives are 3-(1-azulene)-2-(4-hydroxyphenyl) acrylonitrile derivatives obtained through introduction of azulene into a nitrile styrene structure, has an efficient response property to acid, has remarkably enhanced fluorescence after acting with the acid, can be used as an outstanding pH fluorescence enhanced probe and can be used for detecting pH value in water, soil and organisms. Besides, compounds formed by the derivatives and the acid also respond to ultraviolet light, very strong signals are generated in a near-infrared region after irradiation with ultraviolet light, and the compounds can be used as excellent near-infrared fluorochrome to be used for fluorescence labeling in the organisms and cells.

Description

technical field [0001] The invention belongs to the technical field of fluorescent dyes, in particular to an azulene-styrene derivative containing a nitrile group, and a preparation method and application of the compound. Background technique [0002] Due to the advantages of high sensitivity, good selectivity, and easy operation, fluorescence technology is widely used in biological analysis and imaging. The luminescence of traditional fluorescent molecular probes is mainly concentrated in the range of visible light (400-750 nm). At the same time, many organisms and their tissues emit fluorescence when excited by ultraviolet / visible light, which poses a challenge to the fluorescence detection and imaging of biological samples. severe disturbance. The maximum absorption and emission wavelengths of near-infrared fluorescent probes are 600-900 nm, which can avoid the interference of biological samples themselves, and have obvious advantages in the analysis of biological sample...

Claims

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Application Information

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IPC IPC(8): C07C255/36C07C255/37C07C253/30C09K11/06G01N21/64
CPCC07C45/30C07C253/30C07C255/36C07C255/37C09K11/06C09K2211/1007C09K2211/1011G01N21/6428C07C255/38C07C47/445
Inventor 朱亮亮周蕴赟
Owner FUDAN UNIV
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