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Unusually Sensitive Solid State Emissive 1,8-naphthalimide for Detection of Acid Vapors in Turn-off Mode and Base Vapors in Turn-on Mode

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Abstract

A 4-amino-1,8-naphthalimide containing tetramethylpiperidine in N-position was synthesized. The prepared 1,8-naphthalimide was found to possess bright yellow-green fluorescence in a solid state, which could be switched-off in the presence of acid vapors and then switched-on after exposure on base vapors. The observed fluorescence quenching or enhancement, respectively, was more than 10-fold. This behavior was quite opposite to that of the similar 4-oxy-1,8-naphthalimide, in which a well-pronounced PET process operates. In addition, the observed fluorescence quenching was accompanied with color change from yellow to red. Based on these results, the reported 4-amino-1,8-naphthalimide was successfully applied as a reversible solid-state emissive chemosensing material for rapid detection of acid-base vapors for multiple usage.

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The authors declare that the data supporting the findings of this study are available within the article.

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Chemdraw, Origin.

Abbreviations

OLED:

Organic Light Emitting Diodes

ICT:

Intramolecular Charge Transfer

TICT:

Twisted Intramolecular Charge Transfer

PET:

Photoinduced Electron Transfer

FRET:

Fluorescence Resonance Energy Transfer

ESIPT:

Excited State Intramolecular Proton Transfer

AIE:

Aggregation Induced Emission

NMR:

Nuclear Magnetic Resonance

FT-IR:

Fourier Transform Infrared Spectroscopy

UV-VIS:

Ultraviolet Visible Spectroscopy

FQ:

Fluorescence Quenching

DMF:

Dimethylformamide

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Funding

This study is funded by the European Union-NextGenerationEU, through the National Recovery and Resilience Plan of the Republic of Bulgaria, project № BG-RRP-2.004-0002, “BiOrgaMCT”.

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Authors and Affiliations

  1. Department of Organic Synthesis, University of Chemical Technology and Metallurgy, 8 Kliment Ohridsky Bulv, Sofia, 1756, Bulgaria

    Ventsislav V. Bakov, Nikolai I. Georgiev & Vladimir B. Bojinov

  2. Bulgarian Academy of Sciences, Sofia, 1040, Bulgaria

    Vladimir B. Bojinov

Authors
  1. Ventsislav V. Bakov
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  2. Nikolai I. Georgiev
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  3. Vladimir B. Bojinov
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Contributions

Ventsislav V. Bakov: formal analysis, investigation (synthesis, photochemistry, spectral analysis); Nikolai I. Georgiev: conceptualization, methodology, formal analysis, writing - original draft preparation, funding acquisition; Vladimir B. Bojinov: conceptualization, writing - review and editing, supervision, funding acquisition. All authors have read and agreed to the published version of the manuscript.

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Correspondence to Nikolai I. Georgiev or Vladimir B. Bojinov.

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Bakov, V.V., Georgiev, N.I. & Bojinov, V.B. Unusually Sensitive Solid State Emissive 1,8-naphthalimide for Detection of Acid Vapors in Turn-off Mode and Base Vapors in Turn-on Mode. J Fluoresc (2024). https://doi.org/10.1007/s10895-024-03755-0

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