A novel 1,8-naphthalimide-based Cu2+ ion fluorescent probe and its bioimaging application

Wei, Jianhua; Sun, Hao; Jiang, Yan; Miao, Bao-Xi; Han, Xu; Zhao, Yun; Ni, Zhong‐Hai

doi:10.1016/j.saa.2021.120037

Cited by 23 publications

(4 citation statements)

References 39 publications

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“…[ 12 ] To detect Cu 2+ , Ni's group designed a new 1,8‐naphthalimide‐based Schiff base 1 ( Figure ). [ 13 ] Probe 1 , which was prepared by a simple condensation reaction between 2‐butyl‐1,3‐dioxo‐2,3‐dihydro‐1 H ‐benzo[ de ]isoquinoline‐6‐carbaldehyde and 2‐aminophenol, exhibited high sensitivity and selectivity for Cu 2+ over a wide pH range in H 2 O/Tetrahydrofuran (THF) (v/v = 7/3). The fluorescence intensity of free probe 1 is extremely weak.…”

Section: Fluorescent Probes For Detecting Metal Ions Based On Naphtha...mentioning

confidence: 99%

Research Progress on Naphthalimide Fluorescent Probes

Xu,

Xiao,

Liu

et al. 2023

Advanced Sensor Research

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Naphthalimide derivatives are attracting increasing attention as fluorescent probes due to their excellent modifiability and photophysical properties. Their large, rigid coplanar structures and conjugated systems enable easy generation of fluorescence. The imide units and bromonaphthalene functionality offer facile and concise modification pathways in preparing amenable probes for different metal cations, anions, small molecules, and organelles. Therefore, naphthalimide probes have great potential for application in research fields, such as analytical chemistry, cell biology, and clinical diagnosis.

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Section: Fluorescent Probes For Detecting Metal Ions Based On Naphtha...mentioning

confidence: 99%

Research Progress on Naphthalimide Fluorescent Probes

Xu,

Xiao,

Liu

et al. 2023

Advanced Sensor Research

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“…The 1, 8-naphthalimides have a very wide range of applications [1][2] and are often reported extensively as fluorescent dyes, probes and antitumour agents [3][4][5][6][7][8][9][10]. Both the imide site and the naphthalene ring of this class of compounds can be structurally modified and derivatised to obtain new derivatives, showing structural diversity.…”

Section: Introductionmentioning

confidence: 99%

Improvement of Synthesis Process of 4-Amino-1, 8 Naphthalene Anhydride

2023

analc

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Objective: By optimizing the reaction conditions for synthesizing 4-amino-1, 8 naphthalene anhydride compound through three steps of nitration, oxidation and reduction based on the raw material acenaphthene, the yield is improved and the synthesis cost is reduced, so that it can be used for large-scale preparation in the laboratory. Methods: The single variable method was used to explore the effect of temperature conditions on the yield of nitration reaction; to explore the effect of the amount of oxidant, heating and refluxing time, and product post-treatment on the yield of the oxidation reaction; to explore the effect of the amount of absolute ethanol and concentrated hydrochloric acid on the yield of the reduction reaction influences. After the reduction reaction, the gradient elution method of dichloromethane:methanol = 120:1~50:1 was adopted to separate and obtain pure 4-amino-1,8 naphthalene anhydride. Results: The yield of nitration reaction is up to 92.16%, the yield of oxidation reaction is up to 59.49%, and the yield of reduction reaction is up to 77.47%. The purified reduction products are analyzed by 1H-NMR, 13C-NMR and MS (ESI) and the structure was confirmed. Conclusion: The synthesis reaction conditions of 4-amino-1, 8 naphthalene anhydride were optimized, which was helpful for its large-scale preparation in the laboratory, and accumulated important basic experimental data for the industrial production of this compound.

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“…Over the years, the various fluorescent polymers, also including AIE-active small molecules were successfully synthesized for detecting and identifying some metal ions including Al 3+ , Pd 2+ , Fe 3+ and Cu 2+ , explosives, pollutants, biological samples, and the monitoring of some dynamic processes. [14][15][16][17][18][19] To our knowledge, however, the sensitive detection of Zn 2+ on the base of PIE-active polymer is rarely reported until now.…”

Section: Introductionmentioning

confidence: 99%

Preparation and Specific Detection of Zn²⁺ Ions of Polyacylhydrazones with Polymerization‐Induced Emission

Guo,

Huang,

Lin

et al. 2023

Macro Chemistry & Physics

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The trace element Zn2+ plays an important role in the human body, but it is challenging to realize its qualitative and quantitative detection. Herein, inspired by the specific detection of the commercial dithizone to Zn2+, a series of polyacylhydrazones with polymerization‐induced emission (PIE) properties were successfully prepared and applied to the specific recognition and detection of Zn2+. It was found that all selected monomers did not emit fluorescence. In contrast, the as‐prepared polyacylhydrazone could emit strong fluorescence at 455 nm, due to the intramolecular aggregation of acylhydrazone groups along the macromolecular chains, indicating a significant PIE effect. As we expected, the polyacylhydrazone could specifically recognize and detect Zn2+ ions from 17 metal ions by the significantly enhanced fluorescence with a lower limit of detection (LOD) of 66 nM. Additionally, the complexation ratio of 2:1 between the repeating units in polyacylhydrazone and Zn2+, the coordination of Zn2+ with N and O atoms on acylhydrazone groups, and the fluorescence enhancement induced via intramolecular proton transfer were confirmed by 1H NMR and FT‐IR measurements. In conclusion, the successful preparation of PIE‐active polyacylhydrazones and the specific detection of Zn2+ ions provide a useful reference for the molecular design of new functional materials on the base of the traditional detection methods.This article is protected by copyright. All rights reserved

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A novel 1,8-naphthalimide-based Cu2+ ion fluorescent probe and its bioimaging application

Cited by 23 publications

References 39 publications

Research Progress on Naphthalimide Fluorescent Probes

Research Progress on Naphthalimide Fluorescent Probes

Improvement of Synthesis Process of 4-Amino-1, 8 Naphthalene Anhydride

Preparation and Specific Detection of Zn²⁺ Ions of Polyacylhydrazones with Polymerization‐Induced Emission

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A novel 1,8-naphthalimide-based Cu2+ ion fluorescent probe and its bioimaging application

Cited by 23 publications

References 39 publications

Research Progress on Naphthalimide Fluorescent Probes

Research Progress on Naphthalimide Fluorescent Probes

Improvement of Synthesis Process of 4-Amino-1, 8 Naphthalene Anhydride

Preparation and Specific Detection of Zn2+ Ions of Polyacylhydrazones with Polymerization‐Induced Emission

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Product

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Preparation and Specific Detection of Zn²⁺ Ions of Polyacylhydrazones with Polymerization‐Induced Emission