1 and 2 were investigated using TD-PBE0/def2svp (Figure , Figures S6.1-S6.34). The lowest energy singlet and triplet states for 1 and 2 are predominantly represented by ICT transitions between the phenoxazine donor and quinoxaline acceptor moieties involving the HOMO and LUMO as expected (Figures S6.1, S6.3, S6.6, S6.9, S6.33 and S6.34). For 2 the S1 and S2 states are near-degenerate (Figure ) -a consequence of the localisation of the LUMO/ LUMO+1 orbitals of the iptycene core of 2 due to through-space π-system overlap between fins. Such a MO structure is in agreement with established experimental data for triptycene, and indicates that homoconjugation should influence the photophysical properties of 2. Narrow ΔEST values are predicted for 1 and 2 (0.01 and 0.03 eV, respectively).