Highly Ordered Phenanthroline-Fused Azaacene

A new synthetic route to prepare a centrosymmetric phenanthroline-fused azaacene derivative, TIPS-BisPhNPQ, is described. Another axialsymmetric analogue, TIPS-PhNTQ, is also synthesized for comparison. Cyclic voltammetry measurements indicate high electron affinity values of −4.03 and −4.01 eV for TIPS-PhNTQ and TIPS-BisPhNPQ, respectively. Single-crystal X-ray diffraction reveals that TIPS-PhNTQ forms dimers by intermolecular S–N and N–N interaction, while TIPS-BisPhNPQ shows a highly ordered arrangement via two-dimensional brickwork packing and intermolecular hydrogen bonding. The synthetic protocol established in this paper should be highly applicable to the preparation of more azaacene derivatives with extended π-conjugations.