The realization of a train of molecule-gears working under the tip of a scanning tunneling microscope (STM) requires a stable anchor of each molecule to the metal surface. Such an anchor can be promoted by a radical state of the molecule induced by a dissociation reaction. Our results, rationalized by density functional theory calculations, reveal that such an open radical state at the core of star-shaped pentaphenylcyclopentadiene (PPCP) favors anchoring. Furthermore, to allow the transmission of motion by STM manipulation, the molecule-gears should be equipped with specific groups facilitating the tip–molecule interactions. In our case, a tert-butyl group positioned at one tooth end of the gear benefits both the tip-induced manipulation and the monitoring of rotation. With this optimized molecule, we achieve reproducible and stepwise rotations of the single gears and transmit rotations for up to three interlocked units.