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Synthesis and Investigation of Derivatives of 1,8-Naphthalimide with a Red Emission via an Aromatic Nucleophilic Substitution Reaction

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Abstract

1,8-Napthalimides (NIs) have been widely used as fluorescent molecules in biological, chemical, and medical fields because NIs shows high stability and various fluorescence properties under different conditions. However, NIs typically display a fluorescence emission wavelength in the range of 350 – 550 nm which can be notably interfered with by autofluorescence in living cells, significantly limiting their bio-applications. Moreover, low solubility in aqueous media is another major limitation for NIs. In this project, four derivatives of NIs (1–4) have been synthesized via an aromatic nucleophilic substitution reaction and their photophysical properties have been investigated in various media (water, MeOH, MeCN, DMSO, EtOAc, and THF). All of these derivatives (1–4) show a long emission wavelength around 600 nm and high solubility in polar solvents. Particularly molecules (1–4) show the longest emission (624–629 nm) in water and the fluorescence intensity is not significantly varied in the range of pH 4–11. These unique features, long emission wavelength, high solubility, and high stability in difference pH media, will allow these derivative (1–4) to be used as excellent labeling reagents in the biological system.

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Data Availability

All data generated or analyzed during this study are included in this published article.

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Acknowledgements

Authors thank supports from National Institutes of Health (NIH) and Nebraska INBRE program.

Funding

This research work is supported by the National Center for Research Resources (NCRR; 5P20RR016469) and the National Institute for General Medical Science (NIGMS; INBRE-8P20GM103427), a component of the National Institutes of Health (NIH). National center for research resources,5P20RR016469,Chul-Hyun Jeong, national institute of general medical sciences, INBRE-8P20GM103427,Chul-Hyun Jeong

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Authors and Affiliations

  1. Department of Chemistry, University of Nebraska-Kearney, Kearney, NE, US, 68849

    Chul-Hyun Jeong, Aatiya Ahmad, Hannah C. Schmitz & Haishi Cao

Authors
  1. Chul-Hyun Jeong
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  2. Aatiya Ahmad
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  3. Hannah C. Schmitz
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  4. Haishi Cao
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Contributions

Chul-Hyun Jeong performs collection of absorption/emission spectra, data analysis, and writing original draft. Aatiya Ahmad develops the methodology for synthesis. Hannah C. Schmitz synthesizes compounds 2–4. Haishi Cao works as PI for the whole project including preparation of the manuscript.

Corresponding author

Correspondence to Haishi Cao.

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Conflict of Interest

All authors, including Chul-Hyun Jeong, Aatiya Ahmad, Hannah C. Schmitz, and Haishi Cao, declare no conflict of interest.

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Jeong, CH., Ahmad, A., Schmitz, H.C. et al. Synthesis and Investigation of Derivatives of 1,8-Naphthalimide with a Red Emission via an Aromatic Nucleophilic Substitution Reaction. J Fluoresc 32, 427–433 (2022). https://doi.org/10.1007/s10895-021-02853-7

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  • DOI: https://doi.org/10.1007/s10895-021-02853-7

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