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Strong σ-hole activation on icosahedral carborane derivatives for a directional halide recognition.

Crystal engineering based on σ -hole interactions is an emerging approach for realization of new materials with higher complexity. Neutral inorganic clusters derived from 1,2-dicarba- closo -dodecaborane, substituted with -SeMe, -TeMe, and -I moieties on both skeletal carbon vertices are experimentally demonstrated here as outstanding chalcogen- and halogen-bond donors. In particular, these new molecules strongly interact with halide anions in the solid-state. The halide ions are coordinated by one or two donor groups ( μ 1 - and μ 2 -coordinations), to stabilize a discrete monomer or dimer motifs to 1D supramolecular zig-zag chains. Crucially, the observed chalcogen bond and halogen bond interactions feature remarkably short distances and strong directionality. Electrostatic potential calculations further demonstrate the efficiency of the carborane derivatives, with V s,max being similar or even superior to that of reference organic halogen bond donors such as iodopentafluorobenzene.