Edge Decorated Polycyclic Aromatic Hydrocarbons via Oxidative Coupling Approach

Oxidative phenol coupling reduces reliance on halo/metalated substrates needed for conventional redox neutral couplings. A new strategy for construction of polycyclic aromatic hydrocarbons (PAHs) that incorporates oxidative phenol coupling is outlined via a three-stage approach: oxidative fragment coupling, linking of two resultant units, and oxidative cyclization. The protocol allows rapid assembly of both planar and helical systems with a high degree of edge functionalization. The incorporation of 12 alkoxy groups on systems with 12 rings gave rise to lower optical gaps compared to systems with a lesser degree of edge functionalization. Formation of alkoxy highly edge-decorated polycylic aromatic hydrocarbons (PAHs) is described. Oxidative cross coupling of phenols constructs framework vs convetional methods that require prefunctionalization. Smaller optical gaps can be achieved relative to systems of similar size.