Neutral iodotriazoles as scaffolds for stable halogen-bonded assemblies in solution

Leonardo Maugeri, Julia Asencio-Hernández, Tomas Lebl, David Bradford Cordes, Alexandra Martha Zoya Slawin, Marc-André Delsuc, Douglas Philp

Research output: Contribution to journalArticlepeer-review

32 Citations (Scopus)
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Abstract

The halogen bond (XB) donor properties of neutral 1,4-diaryl-5-iodo-1,2,3-triazoles, are explored using a combination of computational and experimental results and are shown to be competitive in halogen bonding efficiency with the classic pentafluoroiodobenzene XB donor. The SNAr reactivity of these donors permits the facile assembly of an iodotriazole functionalised with a 3-oxypyridine XB acceptor, thus generating a molecular scaffold capable of undergoing dimerisation through the formation of two halogen bonds. The formation of this halogen-bonded dimer is demonstrated by 1H and DOSY NMR experiments and a plausible structure generated using DFT calculations.
Original languageEnglish
Pages (from-to)6422-6428
Number of pages7
JournalChemical Science
Volume7
Issue number10
Early online date23 Jun 2016
DOIs
Publication statusPublished - 1 Oct 2016

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