Halogen-Bond-Assisted Guest Inclusion in a Synthetic Cavity

Hiroki Takezawa; Takashi Murase; Giuseppe Resnati; Pierangelo Metrangolo; Makoto Fujita

doi:10.1002/anie.201500994

Halogen-Bond-Assisted Guest Inclusion in a Synthetic Cavity

Angew Chem Int Ed Engl. 2015 Jul 13;54(29):8411-4. doi: 10.1002/anie.201500994. Epub 2015 May 27.

Authors

Hiroki Takezawa¹, Takashi Murase², Giuseppe Resnati³, Pierangelo Metrangolo⁴, Makoto Fujita⁵

Affiliations

¹ Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan).
² Department of Material and Biological Chemistry, Faculty of Science, Yamagata University, 1-4-12 Kojirakawa-machi, Yamagata-shi, Yamagata 990-8560 (Japan).
³ Laboratory of Nanostructured Fluorinated Materials (NFMLab), Department of Chemistry, Materials, and Chemical Engineering "Giulio Natta", Politecnico di Milano, Via L. Mancinelli 7, 20131 Milano (Italy). giuseppe.resnati@polimi.it.
⁴ Laboratory of Nanostructured Fluorinated Materials (NFMLab), Department of Chemistry, Materials, and Chemical Engineering "Giulio Natta", Politecnico di Milano, Via L. Mancinelli 7, 20131 Milano (Italy). pierangelo.metrangolo@polimi.it.
⁵ Department of Applied Chemistry, School of Engineering, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-8656 (Japan). mfujita@appchem.t.u-tokyo.ac.jp.

PMID: 26012524
DOI: 10.1002/anie.201500994

Abstract

The confined space inside a self-assembled cage enhanced halogen bonding (XB) between iodoperfluorocarbons (XB donors) and NO3(-) anions or H2O molecules (XB acceptors), as confirmed by NMR spectroscopy in solution and by X-ray crystallography in the solid state. The cavity also bound an XB donor-acceptor pair, C6F3I3 and C6H5NMe2, in a selective pairwise fashion.

Keywords: halocarbon compounds; halogen bonding; host-guest interactions; molecular recognition; self-assembly.