Halogen bonding two-point recognition with terphenyl derivativesElectronic supplementary information (ESI) available: Experimental details and characterization data, titration data, X-ray structural analyses, details of computations. CCDC 1824277 and 1824278. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8nj00962g

Two-point recognition involving neutral terphenyl-based halogen bond donors (halogen-based Lewis acids) was investigated. Oxadiazole and pyridazole derivatives were identified by DFT as suitable binding partners, even though gas-phase binding was weak. X-ray studies provided convincing evidence of two-point binding in the solid state, while solution data hinted at weak association. Neutral terphenyl-based halogen bond donors form two-point halogen bonding motifs with oxadiazoles in the solid state.