 The theoretical study of the titled model acceptor-bridge-donor molecular series based on 9H-fluoren-9-ylidenemethyl and 1,3,4-oxadiazole heterocycles is presented. The subunits are linked through a thienyl moiety, and the second α-site of oxadiazole was modified. The quantum chemical model indicated that the electron-donating properties of 9H-fluoren-9-ylidenemethyl were significantly supported or suppressed by the terminal substitution of 1,3,4-oxadiazole which affected the possible semiconductivity. Finally, the possible synthesis of selected molecules is described, and the prepared derivatives were fully characterized by 1H NMR, 13C NMR, IR, and elemental analysis together with optical and electrochemical measurements.