This dissertation presents the results of interdisciplinary research, at the crossing of chemistry and physics. Rational design strategies have been developed towards the synthesis of novel molecular machines able to produce a mechanical output at the nanoscale. LT-UHV STM measurements have been performed to manipulate these molecules using electrical voltage pulses as input. Two classes of molecule with different properties have been chosen as core of the designs; azulene due to the high dipole moment when an appropriate substitution pattern is selected and DMBI (1,3 dimethyl 2 phenyl 2,3 dihydro 1 H benzoimidazol) because of the zwitterionic nature. One can assume that these two distinct key features might facilitate a distinct and controllable molecule response to the external electrical field of the STM tip.