Herein, we report a method to pattern a derivatized nifedipine silane monolayer that aromatizes under UV irradiation. Using a functionalized SCS-Pd(II) pincer complex, we demonstrate that a strong metal-coordination complex between the aromatized nifedipine derivative and the pincer complex is formed. This methodology integrates SAM photolithography (top-down) and molecular recognition directed self-assembly (bottom-up) strategies to create simple and rapid synthesizable functional patterned surfaces.