Friction is an important limitation of energy efficiency performances of MEMS/NEMS but is, in the same time, a great opportunity for harvesting energy by designing optimized Tribo-Electric Nano-Generators (TENG). Thus, frictional behaviour can be accurately controlled in real-time by using thermally sensitive periodic patterned self-assembled monolayers of n-octadecyltrichlorosilane (OTS) grafted on MEMS surfaces. Nanopatterns are currently used in order to limit the wear rate without modifying the frictional behaviour. In this work, patterns have been created by micro-contact printing (µCP) using a polydimethylsiloxane (PDMS) stamp displaying a trapezoidal profile. Hence pattern periodicity can be continuously changed-and then optimized from discontinuous to pseudo-continuous-by applying a controlled normal load on the soft PDMS stamp. A multiscale tribological study has been carried out on these nano-patterns by using both single-asperity and multi-asperity nanotribometers. Lateral Force Microscopy (LFM) provides the individual frictional behaviour of each pattern's component whereas the multiasperity nanotribometer rather gives the emerging frictional behaviour induced by the patterning according to temperature. As a macroscopic crucial parameter while designing TENG's devices, this macroscopic behavior has to be carefully optimized for each practical applications at the molecular scale. Thus, whereas the microscale frictional behaviour can be precisely optimized by the pattern's periodicity, the macroscopic one can be accurately controlled with values of friction coefficient ranging from 0.12 to 0.04 by varying the contact temperature. In addition, any inertial effects observed in the thermal-controlled frictional behavior of nano-patterns can be drastically reduced using infra-red emission as thermal source.