Edge-Decorated Polycyclic Aromatic Hydrocarbons by an Oxidative Coupling Approach
Philip Gilmartin1, Cassandra Vu1, Madeline Rotella1
1Department of Chemistry, University of Pennsylvania, Philadelphia, PA, 19104, USA.
Abstract:
Oxidative phenol coupling reduces reliance on halo/metalated substrates used in conventional redox neutral couplings. A new strategy for constructing polycyclic aromatic hydrocarbons (PAHs) that incorporates oxidative phenol coupling is outlined in a three-stage approach: oxidative fragment coupling, linking of the 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.
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