Dibenzophosphapentaphenes: Exploiting P Chemistry for Gap Fine-Tuning and Coordination-Driven Assembly of Planar Polycyclic Aromatic Hydrocarbons

A synthetic route to planar P-modified polycylic aromatic
hydrocarbons
(PAHs) is described. The presence of a reactive σ3,λ3-P moiety within the sp2-carbon scaffold
allows the preparation of a new family of PAHs displaying tunable
optical and redox properties. Their frontier molecular orbitals (MOs)
are derived from the corresponding phosphole MOs and show extended
conjugation with the entire π framework. The coordination ability
of the P center allows the coordination-driven assembly of two molecular
PAHs onto a AuI ion.