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Strong<i>σ</i>‐Hole Activation on Icosahedral Carborane Derivatives for a Directional Halide Recognition

Maxime Beau, Sun Hee Lee, Sooyeon Kim, Won‐Sik Han, Olivier Jeannin, Marc Fourmigué, Emmanuel Aubert, Enrique Espinosa, Ie‐Rang Jeon

2020Angewandte Chemie International Edition28 citationsDOIOpen Access PDF

Abstract

Abstract 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 herein 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 high 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.

Topics & Concepts

Icosahedral symmetryHalideDimerHalogenChemistryCarboraneHalogen bondChalcogenSupramolecular chemistryCrystallographyMoleculeCrystal engineeringCrystal structureStereochemistryInorganic chemistryOrganic chemistryAlkylBoron Compounds in ChemistryCrystallography and molecular interactionsRadioactive element chemistry and processing
Strong<i>σ</i>‐Hole Activation on Icosahedral Carborane Derivatives for a Directional Halide Recognition | Litcius