Novel diamantine monomers, 3-methyl-3-diamantyl methacrylate (MDiMA), 3-ethyl-3-diamantyl methacrylate (EDiMA), and 9-hydroxy-4-diamantyl methacrylate (HDiMA) were synthesized starting from diamantane. Free radical polymerizations of these monomers along with lactone monomers such as γ -butyrolactone methacrylate (GBLMA) were carried out with a goal of obtaining polymers for photoresist applications. Due to their low Ohnishi number and incremental structural parameter (ISP), these diamantane containing polymers are expected to enhance dry etch stability when incorporated into resist formulations. This paper reports the synthesis, characterization and physical properties of MDiMA, EDiMA, HDiMA monomers, some of the polymers made using these monomers for resist applications. In addition, resist performance and etch results of some of the resists made using the diamantane containing polymers are included.