A Halogen-Bond-Induced Triple Helicate Encapsulates Iodide

Casey J. Massena; Nicholas B. Wageling; Daniel A. Decato; Enrique Martin Rodriguez; Ariana M. Rose; Orion B. Berryman

doi:10.1002/anie.201605440

A Halogen-Bond-Induced Triple Helicate Encapsulates Iodide

Casey J. Massena, Nicholas B. Wageling, Daniel A. Decato, Enrique Martin Rodriguez, Ariana M. Rose, Orion B. Berryman

Chemistry and Biochemistry

University of Montana

Research output: Contribution to journal › Article › peer-review

89 Scopus citations

Abstract

The self-assembly of higher-order anion helicates in solution remains an elusive goal. Herein, we present the first triple helicate to encapsulate iodide in organic and aqueous media as well as the solid state. The triple helicate self-assembles from three tricationic arylethynyl strands and resembles a tubular anion channel lined with nine halogen bond donors. Eight strong iodine⋅⋅⋅iodide halogen bonds and numerous buried π-surfaces endow the triplex with remarkable stability, even at elevated temperatures. We suggest that the natural rise of a single-strand helix renders its linear halogen-bond donors non-convergent. Thus, the stringent linearity of halogen bonding is a powerful tool for the synthesis of multi-strand anion helicates.

Original language	English
Pages (from-to)	12398-12402
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	40
DOIs	https://doi.org/10.1002/anie.201605440
State	Published - Sep 26 2016

Funding

This work was funded by the Center for Biomolecular Structure and Dynamics CoBRE (NIH NIGMS grant P20GM103546), National Science Foundation (NSF) CAREER CHE-1555324, Montana University System MREDI 51030-MUSRI2015-02, and the University of Montana (UM). The X-ray crystallographic data were collected using a Bruker D8 Venture, principally supported by NSF MRI CHE-1337908. We thank Allen Oliver and Brian Patrick for valuable crystallographic discussions. Funding for shared instrumentation in the CAMCOR NMR Facility at the University of Oregon was provided by NSF Award CHE-0923589 (MRI/ARRA), CHE-1427987 (MRI) with additional support from the Oregon Nanoscience and Microtechnologies Institute (ONAMI), OregonBEST, and the UO Office for Research and Innovation. We thank Klara Briknarova for help with 2D NMR interpretation, Earle Adams for general NMR guidance, Michael Strain for assistance with DOSY NMR collection and refinement, and Valeriy Smirnov and Ian Chrisman for the use of their glovebox.

Funders	Funder number
CHE-1427987
Center for Biomolecular Structure and Dynamics
CHE-1555324
P20GM103546
MRI CHE-1337908, MREDI 51030-MUSRI2015-02, CHE-0923589
Oregon Nanoscience and Microtechnologies Institute (ONAMI

Keywords

halogen bonding
helical structures
host–guest systems
self-assembly
supramolecular chemistry

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10.1002/anie.201605440

Cite this

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abstract = "The self-assembly of higher-order anion helicates in solution remains an elusive goal. Herein, we present the first triple helicate to encapsulate iodide in organic and aqueous media as well as the solid state. The triple helicate self-assembles from three tricationic arylethynyl strands and resembles a tubular anion channel lined with nine halogen bond donors. Eight strong iodine⋅⋅⋅iodide halogen bonds and numerous buried π-surfaces endow the triplex with remarkable stability, even at elevated temperatures. We suggest that the natural rise of a single-strand helix renders its linear halogen-bond donors non-convergent. Thus, the stringent linearity of halogen bonding is a powerful tool for the synthesis of multi-strand anion helicates.",

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AU - Wageling, Nicholas B.

AU - Decato, Daniel A.

AU - Martin Rodriguez, Enrique

AU - Rose, Ariana M.

AU - Berryman, Orion B.

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AB - The self-assembly of higher-order anion helicates in solution remains an elusive goal. Herein, we present the first triple helicate to encapsulate iodide in organic and aqueous media as well as the solid state. The triple helicate self-assembles from three tricationic arylethynyl strands and resembles a tubular anion channel lined with nine halogen bond donors. Eight strong iodine⋅⋅⋅iodide halogen bonds and numerous buried π-surfaces endow the triplex with remarkable stability, even at elevated temperatures. We suggest that the natural rise of a single-strand helix renders its linear halogen-bond donors non-convergent. Thus, the stringent linearity of halogen bonding is a powerful tool for the synthesis of multi-strand anion helicates.

KW - halogen bonding

KW - helical structures

KW - host–guest systems

KW - self-assembly

KW - supramolecular chemistry

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A Halogen-Bond-Induced Triple Helicate Encapsulates Iodide

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