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A Halogen‐Bond‐Induced Triple Helicate Encapsulates Iodide
Author(s) -
Massena Casey J.,
Wageling Nicholas B.,
Decato Daniel A.,
Martin Rodriguez Enrique,
Rose Ariana M.,
Berryman Orion B.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201605440
Subject(s) - halogen bond , iodide , halogen , chemistry , aqueous solution , triple bond , solid state , ion , iodine , self assembly , combinatorial chemistry , stereochemistry , crystallography , polymer chemistry , inorganic chemistry , organic chemistry , double bond , alkyl
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.