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Anisyl-methoxy Substituted Coumarin Derivatives as Fluorescent Sensors for Detection of Hazardous Nitroaromatics: High Selectivity Towards TNP.

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Title: Anisyl-methoxy Substituted Coumarin Derivatives as Fluorescent Sensors for Detection of Hazardous Nitroaromatics: High Selectivity Towards TNP.
Authors: Nehal, Subhani Khanam1 (AUTHOR), Uppar, Renuka1 (AUTHOR), Karkihalli, Vibha2 (AUTHOR), Basanagouda, Mahanthesh M3 (AUTHOR), Hegdal Math, Suresh Kumar4 (AUTHOR), Javuku, Thipperudrappa1 (AUTHOR) jtrphy2007@gmail.com
Source: Journal of Fluorescence. May2026, Vol. 36 Issue 5, p3605-3622. 18p.
Subjects: Coumarin derivatives, Nitroaromatic compounds, Photoinduced electron transfer, Fluorescent probes, Fluorescence quenching, Explosives detection
Abstract: The detection of nitroaromatic compounds (NACs) is critically important due to their extensive use in explosive materials and the associated environmental and security risks. In this work, three structurally tailored coumarin derivatives 6-chloro-4-(4-methoxyphenoxymethyl)-chromen-2-one (S1), 1-(4-methoxyphenoxymethyl)-benzo[f]chromen-3-one (S2), and 6-methoxy-4-(4-methoxyphenoxymethyl)-chromen-2-one (S3) were explored as fluorescent probes for NAC sensing in Dimethyl sulfoxide (DMSO). Steady-state absorption, emission, and time-resolved spectroscopic investigations revealed significant fluorescence quenching upon gradual addition of nitrobenzene (NB), 2-nitrotoluene (2NT), 4-nitrotoluene (4NT), and 2,4,6-trinitrophenol (TNP). Stern–Volmer (S-V) analysis displayed positive deviations for NB, 2NT and 4NT, suggesting a combined dynamic and static quenching mechanism, whereas negative deviations observed for TNP indicates the major contribution from dynamic quenching mechanism. Fluorescence lifetime measurements confirmed dynamic quenching as the dominant pathway. Thermodynamic analysis revealed negative free energy change (ΔGPET) of the photoinduced electron transfer (PET) values for all coumarin–NAC systems, establishing the favourable nature of the PET process. Among the probes, S2 exhibited superior sensing performance owing to its extended π-conjugation and enhanced donor characteristics, resulting in the highest Stern–Volmer constants and quenching efficiencies. Both solution mode and contact mode studies demonstrated practical applicability, with S2 achieving the lowest detection limit for TNP (2.55 × 10⁻⁶ M). Overall, these findings highlight the potential of rationally designed coumarin derivatives as efficient, cost-effective, and selective fluorescent sensors for nitroaromatic detection, particularly for TNP. [ABSTRACT FROM AUTHOR]
Copyright of Journal of Fluorescence is the property of Springer Nature and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
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  Data: <searchLink fieldCode="DE" term="%22Coumarin+derivatives%22">Coumarin derivatives</searchLink><br /><searchLink fieldCode="DE" term="%22Nitroaromatic+compounds%22">Nitroaromatic compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Photoinduced+electron+transfer%22">Photoinduced electron transfer</searchLink><br /><searchLink fieldCode="DE" term="%22Fluorescent+probes%22">Fluorescent probes</searchLink><br /><searchLink fieldCode="DE" term="%22Fluorescence+quenching%22">Fluorescence quenching</searchLink><br /><searchLink fieldCode="DE" term="%22Explosives+detection%22">Explosives detection</searchLink>
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  Data: The detection of nitroaromatic compounds (NACs) is critically important due to their extensive use in explosive materials and the associated environmental and security risks. In this work, three structurally tailored coumarin derivatives 6-chloro-4-(4-methoxyphenoxymethyl)-chromen-2-one (S1), 1-(4-methoxyphenoxymethyl)-benzo[f]chromen-3-one (S2), and 6-methoxy-4-(4-methoxyphenoxymethyl)-chromen-2-one (S3) were explored as fluorescent probes for NAC sensing in Dimethyl sulfoxide (DMSO). Steady-state absorption, emission, and time-resolved spectroscopic investigations revealed significant fluorescence quenching upon gradual addition of nitrobenzene (NB), 2-nitrotoluene (2NT), 4-nitrotoluene (4NT), and 2,4,6-trinitrophenol (TNP). Stern–Volmer (S-V) analysis displayed positive deviations for NB, 2NT and 4NT, suggesting a combined dynamic and static quenching mechanism, whereas negative deviations observed for TNP indicates the major contribution from dynamic quenching mechanism. Fluorescence lifetime measurements confirmed dynamic quenching as the dominant pathway. Thermodynamic analysis revealed negative free energy change (ΔGPET) of the photoinduced electron transfer (PET) values for all coumarin–NAC systems, establishing the favourable nature of the PET process. Among the probes, S2 exhibited superior sensing performance owing to its extended π-conjugation and enhanced donor characteristics, resulting in the highest Stern–Volmer constants and quenching efficiencies. Both solution mode and contact mode studies demonstrated practical applicability, with S2 achieving the lowest detection limit for TNP (2.55 × 10⁻⁶ M). Overall, these findings highlight the potential of rationally designed coumarin derivatives as efficient, cost-effective, and selective fluorescent sensors for nitroaromatic detection, particularly for TNP. [ABSTRACT FROM AUTHOR]
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  Data: <i>Copyright of Journal of Fluorescence is the property of Springer Nature and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1007/s10895-026-04798-1
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      – Code: eng
        Text: English
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        PageCount: 18
        StartPage: 3605
    Subjects:
      – SubjectFull: Coumarin derivatives
        Type: general
      – SubjectFull: Nitroaromatic compounds
        Type: general
      – SubjectFull: Photoinduced electron transfer
        Type: general
      – SubjectFull: Fluorescent probes
        Type: general
      – SubjectFull: Fluorescence quenching
        Type: general
      – SubjectFull: Explosives detection
        Type: general
    Titles:
      – TitleFull: Anisyl-methoxy Substituted Coumarin Derivatives as Fluorescent Sensors for Detection of Hazardous Nitroaromatics: High Selectivity Towards TNP.
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            NameFull: Nehal, Subhani Khanam
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            NameFull: Uppar, Renuka
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            – D: 01
              M: 05
              Text: May2026
              Type: published
              Y: 2026
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