Molecular Tetris by sequence-specific stacking of hydrogen bonding molecular clips

Abstract

Stacking aromatic molecules through π–π interactions is a useful strategy to create ordered layers of small molecules, but the weak and non-directional nature of these forces creates a challenge in achieving long-range structural ordering. Here, a rigid molecular template that facilitates the creation of a non-collapsible void between two parallel π-faces is designed, and a central N–H motif is shown to increase the thermodynamic stability of self-dimerized assemblies and host–guest complexes via N–H…N hydrogen bonds.