In summary, we have identified the first organic molecules to exhibit a negative singlet-triplet gap in a through-bond CT state. By substituting calicene, which exhibits a Hund's rule violation in upper excited states, the existing inversion is lowered to S1 and T1, a property which is preserved in the excited state geometries. This occurs by tuning the energies of the orbitals corresponding to these states' most significant configurations. The functionalization is shown to reverse the dipole and suppress both the ground-state aromaticity and excited state anti-aromaticity relative to bare calicene.