Calculations predict a notably larger oscillator strength (ƒ) for the S0→S1 transition of 2 than for 1 (ƒ = 0.051 vs. 0.003). ƒ is similarly large for the near-degenerate S0→S2 transition of 2 (ƒ = 0.051). Larger f for the lowest lying singlet states of 2 compared with 1 are promising for enhancements in ɛ and the radiative rate of singlet decay (kr S ) (confirmed experimentally below). Furthermore, within < 0.4 eV of T1 a manifold of 26 higher energy singlet and triplet states are predicted for the iptycene 2 (Figures S6.7-S6.32), in contrast to only 4 for 1