Two organometallic compounds known as (E)-1-ferrocenyl-(3-fluorophenyl)prop-2-en-1-one (Fc1) and (E)-1-ferrocenyl-(3-fluoro-4-methoxyphenyl)prop-2-en-1-one (Fc2) are designed and synthesized for application in dye-sensitized solar cell (DSSC) based on a donor-π-acceptor (D-π-A) architecture. By strategically introducing a methoxy group into the acceptor side of the compound, Fc2 which has adopted a D-π-A-AD structure are compared with the basic D-π-A structure of Fc1. Both compounds were characterized by utilizing the IR, NMR and UV-Vis methods. Target compounds were further investigated by X-ray analysis and studied computationally using Density Functional Theory (DFT) and Time-Dependent DFT (TD-DFT) approaches to explore their potential performances in DSSCs. An additional methoxy group has been proven in enhancing intramolecular charge transfer (ICT) by improving the planarity of Fc2 backbone. This good electronic communication leads to higher HOMO energy level, larger dipole moment and better short-circuit current density (Jsc) values. Eventually, the presence of methoxy group in Fc2 has improved the conversion efficiency as in comparison to Fc1 under the same conditions.
In the title compound, C18H12O3S2, synthesized by the Claisen-Schmidt condensation method, the essentially planar chalcone unit adopts an s-cis configuration with respect to the carbonyl group within the ethyl-enic bridge. In the crystal, weak C-H⋯π inter-actions connect the mol-ecules into zigzag chains along the b-axis direction. The mol-ecular structure was optimized geometrically using Density Functional Theory (DFT) calculations at the B3LYP/6-311 G++(d,p) basis set level and compared with the experimental values. Mol-ecular orbital calculations providing electron-density plots of HOMO and LUMO mol-ecular orbitals and mol-ecular electrostatic potentials (MEP) were also computed both with the DFT/B3LYP/6-311 G++(d,p) basis set. The experimental energy gap is 3.18 eV, whereas the theoretical HOMO-LUMO energy gap value is 2.73 eV. Hirshfeld surface analysis was used to further investigate the weak inter-actions present.