We describe reproducible protocols for the chemisorption of self-assembled monolayers (SAMs), useful as imaging layers for nanolithography applications, from p-chloromethylphenyltrichlorosilane (CMPS) and 1-(dimethylchlorosilyl)-2-(p,m-chloromethylphenyl)ethane on native oxide Si wafers. Film chemisorption was monitored and characterized using water contact angle, X-ray photoelectron spectroscopy, and ellipsometry measurements. Atomic force microscopy was used to monitor the onset of multilayer deposition for CMPS films, ultimately allowing film macroscopic proper-ties to be correlated with their surface coverage and nanoscale morphologies. Although our results indicate the deposition of moderate coverage, disordered SAMs under our conditions, their quality is sufficient for the fabrication of sub-100-nm-resolution metal features. The significance of our observations on the design of future imaging layers capable of molecular scale resolution in nanolithography applications is briefly discussed.