Self-assembly of tris(ureidobenzyl)amines: flexible bricks for robust architectures

Despite their high degree of flexibility, tribenzylamine molecules endowed with one ureido group in every arm are avid self-assemblers with a high capacity for self-recognition. Narcissistic self-sorting or chiral self-discrimination events take place when two modules associate giving capsular aggregates. The size of the cavity may be modulated by the relative position of the ureido group and the amino function works as a pH switch of the rupture–reassembly process. When chiral racemic triureas are present the self-assembly is highly diastereoselective.