Solid state packing
plays a critical role in molecular materials
to be applied within the area of organic electronics since the arrangement
of molecules conditions the quality of the charge transport. Due to
the difficulty in accurately predicting the crystal packing simply
from the molecular structure, the design of molecules which can self-organize
using strategically located functional groups becomes a useful approach
to induce certain order directed by noncovalent interactions. The
orientation of these interactions can be intentionally controlled
from the early stage of molecular design and contribute to restrict
the randomness of molecular arrangement in the solid state. Herein,
we describe the synthesis and solid state characterization of a novel
fused polyheteroaromatic system incorporating hydrogen bond donor
and acceptor sites directly into a pentacyclic structure without disrupting
its conjugation. A comparative study with an analogous system without
hydrogen bond acceptor sites shows the remarkable effect of the hydrogen
bond-directed assembly on the crystal packing and the benefits on
the π–π intermolecular overlap, crucial for charge
transport processes in organic semiconductors