Synthesis and Electronic Properties of Triperyleno[3.3.3]Propellanes: Towards Two-Dimensional Electronic Structures.

Threefold symmetric triperyleno[3.3.3]propellanes (TPRPs), which are composed of three perylene units peri-fused on [3.3.3]proppellane, have been synthesized and their electronic properties characterized. Unsubstituted TPRP assembles into two-dimensional honeycomb-like networks. TPRP displays a bathochromic-shifted absorption band in its absorption spectrum and shows well-separated one-electron redox waves in a cyclic voltammogram, due to a homoconjugative interaction between perylene moieties. A radical cation species of tert-butyl substituted TPRP shows spin delocalization over the whole of the molecule, which is derived from effective overlap of HOMOs among three perylene moieties.