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Discrete polymers offer an excellent platform for comprehending the interplay between precise chain structures, distinctive self‐assembly behavior, and functional applications, whereas the development of discrete polymers with self‐immolative properties remains scarce. Here, we modularly synthesize a library of discrete self‐immolative oligourethanes containing N‐naphthylcarbamate or N‐(3‐fluorophenyl)carbamate...