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N.Br halogen bonding: one-dimensional infinite chains through the self-assembly of dibromotetrafluorobenzenes with dipyridyl derivatives
Authors:De Santis Alessandra  Forni Alessandra  Liantonio Rosalba  Metrangolo Pierangelo  Pilati Tullio  Resnati Giuseppe
Institution:The G Natta Department of Chemistry, Materials, and Chemical Engineering, Polytechnic of Milan 7, via Mancinelli, 20131 Milan, Italy.
Abstract:The N.Br halogen bonding drives the self-assembly of 1,4-dibromotetrafluorobenzene (1 a) and its 1,3 or 1,2 analogues (1 b,c, respectively) with dipyridyl derivatives 2 a,b. The isomeric supramolecular architectures 3 a-f are obtained as cocrystals that are stable in the air at room temperature. The solid-state features of these 1D infinite chains 3 have been fully characterized by single-crystal X-ray, Raman, and IR analyses. The occurrence of N.Br halogen bonding in solution has been detected with (19)F NMR spectroscopy. The N.Br halogen bonding is highly selective and directional and the geometry of the single strands of noncovalent copolymers 3 is programmed by the geometry of halogen-bonding donor and acceptor sites on the starting modules. The composition and topology of the instructed networks can be predicted with great accuracy. Experiments of competitive cocrystal formation established the strength of the N.Br interaction relative to other halogen bondings and the ability of different modules 1 to be involved in site-selective supramolecular syntheses.
Keywords:bromine  fluorine  halogen bonding  self‐assembly  supramolecular chemistry
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