A Divergent Route to Diversity in Macromolecules

[reaction: see text] A synthetic route for obtaining functional group diversity in macromolecules is described. The route relies on the differential reactivity of substituted dichlorotriazines. Treatment of a triamine core with substituted dichlorotriazines cleanly yields tris(monochlorotriazines). Subsequent S(N)Ar reactions with amine nucleophiles bearing the functional group of interest yield diversity. If the substituent on the dichlorotriazine is a protected nucleophile, deprotection of the functionalized core allows for iterative reactions and the synthesis of star, dendritic, and hybrid macromolecules.