Two-dimensional bricklayer arrangements of tolans using halogen bonding interactionsElectronic supplementary information (ESI) available: Complete synthetic and crystallographic details. CCDC 1054201-1054206. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5cc02225h

Diphenylacetylene (tolan) derivatives with self-complementary aryl halides and halogen bond-accepting nitriles form 2D bricklayer packing motifs when halogen bonding occurs. When halogen bonding is absent, as occurred with fluorinated aryl bromides, the molecules adopt other packing motifs. These results suggest halogen bonding is potentially useful for producing rarely observed 2D bricklayer motifs in organic semiconductors. Diphenylacetylene (tolan) derivatives with self-complementary aryl halides and halogen bond-accepting nitriles form 2D bricklayer packing motifs when halogen bonding occurs.