Synthesis, structural investigation and computational analysis on a new chalcone derivative: (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(2-chloro-6-fluorophenyl)prop-2-en-1-one

Abstract

The new chalcone derivative namely, ( E )-1-(benzo[ d ][1,3]dioxol-5-yl)-3-(2‑chloro-6-fluorophenyl)prop‑2-en-1-one (BCFC) was successfully synthesized via Claisen-Schmidt condensation method with a mixture of 2‑chloro-6-fluorobenzaldehyde and 1-(benzo[ d ][1,3]dioxol-5-yl)ethenone. From the single crystal X-ray diffraction analysis, the molecular structure of BCFC shows s-cis configuration with respect to the enone moiety and further stabilized via intramolecular C—H•••F interaction. The planar structure of BCFC further helps to increase the charge transfer within the molecules. There is no significant interaction observed, which is further confirmed by the Hirshfeld fingerprint plot analysis. The optimized molecular structure at the ground state was then calculated by implementing the Density Functional Theory (DFT) method with a B3LYP/6–311 G (d,p) basis set and further reveals the molecular electrostatic potential (MEP) and HOMO–LUMO energy band of BCFC . The red region of the carbonyl group at the enone bridge of BCFC demonstrates the electrophilic attack side and acts as a good acceptor part. In addition, the small HOMO-LUMO energy gap (2.33 eV) shows the suitability of BCFC as a future optoelectronic material. A new halogenated chalcone derivatives have been synthesized and structurally characterized by single crystal XRD and UV–Vis method. The results are compared with the density functional theory (DFT) method with B3LYP/6–311 G ++ (d,p) level. The energies of HOMO LUMO as the energy gaps are calculated for both compounds. The DFT analyses were theoretically computed. The UV–Vis and Hirshfeld surface for the BCFC system are further discussed.