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Naphthalimide-rhodamine-based compound and application thereof

A technology of naphthalimide and compound is applied in the field of compounds based on naphthalimide-rhodamine, and achieves the effects of rapid detection, easy post-processing and good selectivity

Inactive Publication Date: 2018-09-11
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, it remains a challenge to design and synthesize novel ratiometric sensors with dual-channel fluorescence-enhanced responses and suitable for the detection of Hg ions in environmental and biological systems.

Method used

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  • Naphthalimide-rhodamine-based compound and application thereof
  • Naphthalimide-rhodamine-based compound and application thereof
  • Naphthalimide-rhodamine-based compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Preparation of target compound I-1

[0069]

[0070] (1) Synthesis of compound IV-1

[0071] 4-(2-Aminoethyl)morpholine (2.5g, 18mmol) and 4-bromo-1,8-naphthalic anhydride (2.5g, 9mmol) were dissolved in 50mL of ethanol, and the mixture was refluxed overnight, then cooled to At room temperature, the gray crude product was collected by filtration and then purified by column chromatography (eluent: dichloromethane) to obtain 3.07 g of off-white solid with a yield of 87%. 1 H NMR (400MHz, CDCl 3 )δ (ppm): 8.66 (d, J = 7.2, 1H), 8.58 (d, J = 8.4, 1H), 8.41 (d, J = 8.0, 1H), 8.05 (d, J = 8.0, 1H), 7.86(t, J=7.6,1H), 4.35(t, J=6.8,2H), 3.69(t, J=4.4,4H), 2.72(t, J=6.8,2H), 2.61(br,4H) .

[0072] The synthetic route is as follows:

[0073]

[0074] (2) Synthesis of compound Ⅵ-1

[0075] Add 2M K 2 CO 3 aqueous solution (10mL), add tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (100mg, 0.08mmol), and the mixture was refluxed under nitrogen protection. ...

Embodiment 2

[0086] Compound I-1 changes in fluorescence spectrum with the increase of mercury ion addition:

[0087] The compound I-1 prepared in Example 1 was dissolved in a solution of ethanol and deionized water, the volume ratio of ethanol and deionized water was 5:1, and a 20 μM test stock solution was prepared, and different equivalents (0-30eq) were added Mercury ion standard solution, with 400nm as excitation light, measure its fluorescence properties, fluorescence spectrum as image 3 as shown, image 3 It is the fluorescence spectrogram of adding different amounts of mercury ions in the compound I-1 prepared in Example 1, by image 3 It can be seen that with the addition of mercury ions, the fluorescence intensity of the naphthalimide part increases gradually, and slowly red shifts to 480nm. At the same time, the characteristic emission peak corresponding to the ring-opening of rhodamine appeared at 585nm, and gradually increased with the addition of mercury ions. This phenom...

Embodiment 3

[0089] Selectivity of Compound I-1 to Different Molecules or Ions

[0090] Take out 3mL respectively from the 20 μ M test stock solution in the embodiment 2 and add in the cuvette, add 30 times of equivalent competing molecular standard solutions, one of them adds the mercury ion standard solution of equimolar quantity, with 400nm as excitation light, detection solution Fluorescence emission spectrum changes, the results are as follows Figure 4 as shown, Figure 4 It is the selective fluorescence spectrogram of compound I-1 prepared in Example 1 to different ions. Depend on Figure 4 It can be seen that other metal ions have almost no effect on the fluorescence of compound I-1, but the addition of mercury ion solution significantly enhances the fluorescence of compound I-1 at 480nm and 585nm.

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Abstract

The invention discloses a naphthalimide-rhodamine-based compound. The compound is represented by general formula (I) shown in the description, and all substituent groups in the formula (I) are as defined in the description. The invention also discloses a detection composition and a detection kit of the naphthalimide-rhodamine-based compound, and a use of the detection composition or the detectionkit in the detection of mercury ions in a water environment and a biological cell system as a fluorescent probe for lysosomal targeted detection of mercury ions. The compound realizes the rapid detection of mercury ions by the fluorescent probe, has a good selectivity, and is a fluorescent probe having a chromogenic sensing function.

Description

technical field [0001] The invention relates to the technical field of fluorescence sensors, in particular to a naphthalimide-rhodamine-based compound and applications thereof. Background technique [0002] In recent years, the development of fluorescent probes for the detection of heavy metal ions and transition metal ions has received considerable attention because of the importance of these ions in chemical, biological, and environmental analysis. Among these metal ions, mercury ions are known for their particularly high toxicity, which can cause serious damage to human health even at extremely low concentrations. Therefore, searching for a selective and efficient analytical method to detect Hg in aqueous solution 2+ It is of considerable significance and has become an important topic in current chemical research. [0003] With the development and application of ratiometric fluorescent probes, the development of effective ratiometric probes has attracted people's intere...

Claims

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Application Information

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IPC IPC(8): C07D491/107C09K11/06G01N21/64G01N21/78
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1033C09K2211/1088C09K2211/1092G01N21/643G01N21/6486G01N21/78G01N2021/6432
Inventor 王成云袁晓李纪珍赵丹顾沁莹
Owner EAST CHINA UNIV OF SCI & TECH
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