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The grafting of molecular layers to carbon-based materials provides a way to combine the high chemical and thermal stability of these materials with surface properties such as chemical recognition or reactivity. The functionalization of surfaces with ultraviolet light has emerged as a way to modify difficult-to-functionalize materials, such as diamond. We have performed a combined experimental and computational investigation of the photochemical reaction of terminal alkenes with hydrogen-terminated carbon surfaces. 1-Alkenes carrying various terminal functional groups (−NHCOCF₃, −NHCOO(tert-butyl), −COOCH₃, −CH₃) were grafted from the neat liquids using 254 nm light. These layers were characterized using X-ray Photoelectron Spectroscopy and Infrared Reflectance Absorption Spectroscopy. Pronounced differences in reactivity were observed between the molecules:  trifluoroacetamide-terminated …