When designing and employing lubricants, film thickness modeling techniques must be used as part of an overall design approach to insure mating components, in relative motion have proper lubricating films to separate surface asperities. Improper asperity separation will lead to increased friction and wear, and overall reduce system reliability, serviceability, and efficiency. Many of the tools to model tribofilms used today are rooted in empirical studies completed with hydrocarbon based fluids as the lubricating medium. Generally, these modeling techniques have also been applied to non-hydrocarbon based lubricants, and this may not be an accurate method to model such fluids. As demands for improved lubricant performance continue to rise, so too does the need for improved tribofilms modeling techniques. This paper will discuss a modeling techniques developed, in which, silicone based polymer molecular structures are designed with tribological film performance in mind. The models consider molecular structures of various traditional and newly developed silicone fluids, and relate that structure to rheological performance. Expected rheological performance is then used to model tribological film formation and characteristics. The output of these tribological film formation and characteristic models can then be fed back to the molecular structure module and iterated to achieve optimal molecular structure for the intended tribological performance. In addition, a graphical user interface has also been developed to aid in the data input to the modeling software.