Spectral, TD-DFT, and metal sensing investigations of four chromone-based compounds

• Published in: Journal of molecular structure 2025-03, Vol.1325, Article 141029
• Main Authors: Al-Thani, Aisha F.A.A., Ba-Busail, Fatima E.A., Fadaly, Maryam K.S., Shraim, Amjad M., Salih, Kifah S.M.
• Format: Article
• Language: English
• Subjects: Chemosensing; Chromone; Colorimetry; Fluorescence; Imine; TD-DFT
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2024.141029

•New C-3 functionalized chromones were synthesized and characterized.•The basis of electronic absorptions was chased using TD-DFT•The energy gaps of the compounds were assessed experimentally and computationally.•Binding ability of a model compound towards several metal(loids) was investigated in different organic solvents.•The model compound could serve as a colorimetric and fluorimetric chemosensor, e.g.: Cu2+, Zn2+, As3+, etc. Four C-3 functionalized chromones (3a-d) were synthesized from a typical condensation of diaminomaleonitrile and 3-formylchromone precursors in acetonitrile under reflux conditions. The prepared materials were spectroscopically characterized using elemental analysis (C, H and N), UV–Vis, FT-IR, 1H, 19F, and 13C NMR. Furthermore, computational investigations were performed to pursue the experimental outcomes; the basis of electronic absorptions was chased using Time-Dependent Density Functional Theory (TD-DFT). Visualization of the electrostatic potential demonstrated that the prepared materials possess principally comparable electronic distributions along with electrophilic and nucleophilic cores. These cores could play an essential role in settling the molecular structures through different forces, including H-bonding and C-H···π attractive force. The estimated energy gap (ΔE) of the new derivatives was figured out to be 3.069, 3.066, 3.071 and 2.765 eV, respectively for 3a-d. Such values are needed for electron promotion from HOMO to LUMO; additionally, they were employed to explore the values of structure stability and the overall chemical reactivity. Aiming to develop sensitive and selective metal chemosensors, the preliminary binding ability of 3a, as a model, towards several metals and metalloids was investigated in different organic solvents. Our preliminary finding indicated that 3a could serve as a colorimetric and fluorimetric chemosensor for some transition metals (e.g., Cu and Zn) and arsenic species (e.g., arsenite and methylarsonate) in solution.