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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 12-14 rings gave rise to lower optical gaps compared to systems with a lesser degree of edge functionalization.

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