Highly Ordered Phenanthroline-Fused Azaacene

Abstract

A new synthetic route to prepare a centrosymmetric phenanthroline-fused azaacene derivative, <b>TIPS-BisPhNPQ</b>, is described. Another axialsymmetric analogue, <b>TIPS-PhNTQ</b>, is also synthesized for comparison. Cyclic voltammetry measurements indicate high electron affinity values of −4.03 and −4.01 eV for <b>TIPS-PhNTQ</b> and <b>TIPS-BisPhNPQ</b>, respectively. Single-crystal X-ray diffraction reveals that <b>TIPS-PhNTQ</b> forms dimers by intermolecular S–N and N–N interaction, while <b>TIPS-BisPhNPQ</b> 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