From a Tinkertoy® kit of molecular-sized rotators, axles, and mounting groups, molecular rotors have been designed and synthesized in the Michl group for mounting on silica surfaces. Full and mixed monolayer arrays of various rotors and diluent molecules have been deposited on silica through chemisorption, via the silicon atom of R-Si(OiPr)₃ and R-Si(OEt)₃ (R = axle and rotator) groups, and by physisorption of the calcium salts of fatty acids using Langmuir-Blodgett techniques. In this dissertation, the different deposition methods are assessed in terms of their ability to form oriented monolayer arrays as characterized by ellipsometry, UV-Vis, and grazing-incidence ATR FTIR spectroscopy. Molecular mechanics calculations of rotors and films elucidate some of the spectroscopic results and have been used as a predictive tool to improve our rotor design. Calculations, along with spectroscopic considerations, have also led to the development of a new, carbostyril-based chromophore to be used as a rotator. Experimental considerations for the observation of surface-mounted rotor rotation are also discussed.