Supramolecular macrocycles reversibly assembled by Te…O chalcogen bonding

Peter C. Ho, Patrick Szydlowski, Jocelyn Sinclair, Philip J. W. Elder, Joachim Kübel, Chris Gendy, Lucia Myongwon Lee, Hilary Jenkins, James F. Britten, Derek R. Morim and Ignacio Vargas-Baca ()
Additional contact information
Peter C. Ho: McMaster University
Patrick Szydlowski: McMaster University
Jocelyn Sinclair: McMaster University
Philip J. W. Elder: McMaster University
Joachim Kübel: McMaster University
Chris Gendy: McMaster University
Lucia Myongwon Lee: McMaster University
Hilary Jenkins: McMaster University
James F. Britten: McMaster University
Derek R. Morim: McMaster University
Ignacio Vargas-Baca: McMaster University

Nature Communications, 2016, vol. 7, issue 1, 1-10

Abstract: Abstract Organic molecules with heavy main-group elements frequently form supramolecular links to electron-rich centres. One particular case of such interactions is halogen bonding. Most studies of this phenomenon have been concerned with either dimers or infinitely extended structures (polymers and lattices) but well-defined cyclic structures remain elusive. Here we present oligomeric aggregates of heterocycles that are linked by chalcogen-centered interactions and behave as genuine macrocyclic species. The molecules of 3-methyl-5-phenyl-1,2-tellurazole 2-oxide assemble a variety of supramolecular aggregates that includes cyclic tetramers and hexamers, as well as a helical polymer. In all these aggregates, the building blocks are connected by Te…O–N bridges. Nuclear magnetic resonance spectroscopic experiments demonstrate that the two types of annular aggregates are persistent in solution. These self-assembled structures form coordination complexes with transition-metal ions, act as fullerene receptors and host small molecules in a crystal.

Date: 2016
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DOI: 10.1038/ncomms11299

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