ArticleMolecules (Basel, Switzerland)2023
Theoretical Investigation on the "ON-OFF" Mechanism of a Fluorescent Probe for Thiophenols: Photoinduced Electron Transfer and Intramolecular Charge Transfer.
Article in Molecules (Basel, Switzerland), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed, 11 citations in OpenAlex.
- Naphthalimide Derivatives with Extended Heterocyclic Systems-Synthesis, Spectral and Sensing Properties.Sensors (Basel, Switzerland) · 2026Article
- Modulating the ESIPT Mechanism and Luminescence Characteristics of Two Reversible Fluorescent Probes by Solvent Polarity: A Novel Perspective.Molecules (Basel, Switzerland) · 2024Article
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5 authors at 1 institution in 1 country.
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Abstract
In this study, the sensing mechanism of (2E,4E)-5-(4-(dimethylamino)phenyl)-1-(2-(2,4dinitrophenoxy)phenyl)penta-2,4-dien-1-one (DAPH-DNP) towards thiophenols was investigated by density functional theory (DFT) and time-dependent DFT (TD-DFT). The DNP group plays an important role in charge transfer excitation. Due to the typical donor-excited photo-induced electron transfer (d-PET) process, DAPH-DNP has fluorescence quenching behavior. After the thiolysis reaction between DAPH-DNP and thiophenol, the hydroxyl group is released, and DAPH is generated with the reaction showing strong fluorescence. The fluorescence enhancement of DAPH is not caused by an excited-state intramolecular proton transfer (ESIPT) process. The potential energy curves (PECs) show that DAPH-keto is less stable than DAPH-enol. The frontier molecular orbitals (FMOs) of DAPH show that the excitation process is accompanied by intramolecular charger transfer (ICT), and the corresponding character of DAPH was further confirmed by hole-electron and interfragment charge transfer (IFCT) analysis methods. Above all, the sensing mechanism of the turn-on type probe DAPH-DNP towards thiophenol is based on the PET mechanism.
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