Columnar/Lamellar Packing in Cocrystals of Arylbipyridines with Diiodoperfluorobenzene

Stimulated by strongly directional C-I center dot center dot center dot N noncovalent halogen bonding, pi-hole center dot center dot center dot pi and pi-pi interactions, cocrystals of nonplanar 4-arylated-2,2'-bipyridine (ArB) derivatives with 1,4-diiodo-tetrafluorobenzene (D) were generated which exhibit a promising columnar/lamellar packing arrangement. Hirshfeld surface, quantum theory of atoms in molecules, and electrostatic potential surface analyses were employed to examine the weak intermolecular interactions governing the packing arrangement in ArB crystals and corresponding cocrystals with D (ArB center dot D). Cocrystals of 4-phenyl-2,2'-bipyridine (PhB) and 4-(naphthalen-1-yl)-2,2'-bipyridine (NaB) with D [PhB center dot D1, PhB center dot D2, (NaB)(2)center dot D-2,D-5, and (NaB)(3)center dot D-2] exhibited C-I center dot center dot center dot N directed infinite one-dimensional chains of alternate ArB and D units. In contrast, C-I center dot center dot center dot Ninteraction's guide the formation of termolecular complexes in the cocrystal of 4-(phenanthren-9-y1)-2,2'-bipyridine with D (PhenB center dot D-0.5). Successful implementation of C-I center dot center dot center dot N interactions aided, by 2,2'-bipyridine and D enabled the tuning of threedimensional close packing in planar polyaromatic hydrocarbons into a columnar/lamellar arrangement suitable for optoelectronic devices.