Large Non-planar Conjugated Molecule with Strong Intermolecular Interactions Achieved with Homoleptic Zn(II) Complex of Di(5-quinolylethynyl)-tetraphenylazadipyrromethene

Zinc­(II) complexes of tetraphenylazadipyrromethenes
are potential
non-planar n-type conjugated materials. To tune the
properties, we installed 5-quinolylethynyl groups at the pyrrolic
positions. Compared to the complex with 1-napthylethynyl, we found
evidence for stronger intermolecular interactions in the new complex,
including much higher overlap integrals in crystals. X-ray analysis
revealed unconventional C–H···N hydrogen bonding
between two quinolyls of neighboring molecules, pointing to a new
strategy for the development of non-planar molecular semiconductors
with stronger intermolecular interactions.