© 2022 Elsevier B.V.The donor-acceptor type indole chromophore motif presents an interesting molecular architecture to the scientific world, unfortunately, as in every special and beautiful formation needed; their synthesis represents a synthesis challenge. In the current search, new donor-acceptor typed indole derivatives, 1-methyl-phenyl-3-aldehyde indole (HAN-1), 2-((1-methyl-2-phenyl-1H-indol-3-yl)methylene)malononitrile (HAN-2), 1-ethyl-2-phenyl-3-aldehyde indole (HAN-3), 2-((1-ethyl-2-phenyl-1H-indol-3-yl)methylene)malononitrile (HAN-4) were successfully synthesized and the results supported with FTIR and NMR spectra analysis. All the molecules undergo excited state intramolecular electron transfer with unique charge transfer reaction. Their electrochemical and optical properties were investigated in relation to the acceptor effect of functional groups on the indole units in the conjugated structure. Density functional theory (DFT) calculations exhibited that higher electron withdrawing ability strength resulted in decreased HOMO-LUMU gaps of the molecules. Futhermore, donor acceptor typed indole derivatives undergo irreversibly one electron oxidation in the medium of 0.1 M TBAPF6/ACN solution with a similar onset oxidation potentials. Both experimental and theoretical studies showed that the electron withdrawing ability of the molecules affect more LUMO energy level of the molecules. Moreover, they suggest that donor acceptor indole molecules herein are potential candidates for fabrication of dye synthesized solar cells.