Stacked Fluoroaromatics as Supramolecular Synthons for Programming Protein Dimerization Specificity

Aromatic “bonding”: Although known to exist in proteins, aromatic stacking interactions and the energetic factors important for it are not well understood. A systematic investigation of aromatic stacking interactions in a protein model system using a series of fluorinated phenylalanine analogues illustrates the importance of dipole–dipole and dipole–induced-dipole coupling to the stability and self-sorting properties of aromatic stacking pairs.