text: Sigma hole interactions have applications in a variety of fields. The ability to induce stabilizing and strongly directional intermolecular interactions which can be easily tuned via minor structural substitutions makes leveraging these interactions particularly value in fields in which control over supramolecular organization is desired. As such, sigma hole interactions have been used in the field of crystal engineering to design molecular building blocks for self-assembly, to improve the properties of liquid crystals, and to design magnetic materials.