1 and 2 display identical first oxidation potentials (E ox ) (Figure , Table .1), consistent with localisation of the HOMO of 2 on the peripheral phenoxazine donors. Conversely, 2 displays a less negative first reduction potential (E red ) than 1, and hence a more accessible LUMO, ascribed to electronic communication across the iptycene core of 2, which increases the acceptor strength. Additionally, while the first reduction wave for 1 corresponds to what is typically expected for a single electrochemically reversible process, the wave for 2 is clearly a superposition of three electrochemical reductions. This electrochemical behavior supports weak electronic coupling between the multiple fins of 2 through the lower lying unoccupied molecular orbitals, consistent with homoconjugation and the DFT predictions above.