Here, we use TPyP and TBAP to also investigate the effect of pyridyl and benzoic acid groups on the extended packing of pyrene cores. Hydrogen bonding has been shown to have the potential to frustrate dense packing of organic molecules, and to generate electrostaticallystabilized, low-density, hydrogen bonded organic frameworks (HOFs). Similarly, labile C-H•••N bonding interactions in molecular crystals, comprising pyridyl functionalized molecules, have been used to stabilize low density crystal packings. Hence, TPyP and TBAP both feature functional groups that have the potential to direct low-density, porous crystal packings with extended π-stacks, which is attractive for organic photocatalysts.