Columnar/Lamellar Packing in Cocrystals of Arylbipyridines with Diiodoperfluorobenzene

• DOI: 10.1021/acs.cgd.6b00968
• Publication Date: 2016-09-15T19:41:15Z
• Authors: Remya Ramakrishnan; Ajith R. Mallia; M. A. Niyas; Ramarani Sethy; Mahesh Hariharan
• Keywords: Cocrystal; 4,4'-Bipyridine; Bipyridine; Non-covalent interactions; 2,2'-Bipyridine; Crystal Engineering

Stimulated by strongly directional C–I···N noncovalent halogen bonding, π-hole···π and π–π 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 atoms in molecules, electrostatic potential surface analyses employed to examine the weak intermolecular interactions governing arrangement ArB crystals corresponding D (ArB·D). Cocrystals 4-phenyl-2,2′-bipyridine (PhB) 4-(naphthalen-1-yl)-2,2′-bipyridine (NaB) [PhB·D1, PhB·D2, (NaB)2·D2.5, (NaB)3·D2] exhibited directed infinite one-dimensional chains alternate units. In contrast, guide formation termolecular complexes cocrystal 4-(phenanthren-9-yl)-2,2′-bipyridine (PhenB·D0.5). Successful implementation aided 2,2′-bipyridine enabled tuning three-dimensional close planar polyaromatic hydrocarbons into suitable for optoelectronic devices.