The long-awaited synthesis and self-assembly of a small rigid C 3 -symmetric trilactam.

The challenging synthesis of a fused C 3 -symmetric trilactam (1) was executed in racemic and enantiomerically pure form. The rigidity, symmetry and high density of hydrogen bonding motifs make 1 an attractive candidate for self-assembly study, which revealed different hydrogen bond patterns in the crystals of rac -1- d 3 and (+)-( SSS )-1.