Imaging the halogen bond in self-assembled halogenbenzenes on silver

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Science  13 Oct 2017:
Vol. 358, Issue 6360, pp. 206-210
DOI: 10.1126/science.aai8625

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Visualizing halogen bonding

Even though halogen atoms are highly electronegative, a noncovalent bond can form between an electron donor and a halogen atom in a covalent bond. Such interactions are facilitated by the formation of electron-depleted regions in the halogen's covalent bond, a situation least likely for fluorine atoms. Han et al. used noncontact scanning tunneling microscopy with submolecular resolution to explore how the size and polarizability of halogens affect complex formation by halogenated benzene molecules adsorbed on a silver surface (see the Perspective by Neaton). With the help of density functional theory, they show how several weak interactions, including van der Waals forces, electrostatic repulsions, and halogen bonds, affect structure.

Science, this issue p. 206; see also p. 167


Halogens are among the most electronegative elements, and the variations in size and polarizability of halogens require different descriptions of the intermolecular bonds they form. Here we use the inelastic tunneling probe (itProbe) to acquire real-space imaging of intermolecular-bonding structures in the two-dimensional self-assembly of halogenbenzene molecules on a metal surface. Direct visualization is obtained for the intermolecular attraction and the “windmill” pattern of bonding among the fully halogenated molecules. Our results provide a hitherto missing understanding of the nature of the halogen bond.

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