Competitive Hydrogen Bonding in π‐Stacked Oligomers

A theoretical study showing the importance of intra- and intermolecular hydrogen bonding in the formation of self-assembled systems is reported. Arene-based species with appropriate functional groups to favor intermolecular hydrogen bonding are studied. It is found that molecular flexibility can create strong intermolecular hydrogen bonds within oligomers in which molecules are generally separated by large interplanar distances (see figure).