Cooperative Binding in a Phosphine Oxide-Based Halogen Bonded Dimer Drives Supramolecular Oligomerization

Leonardo Maugeri, Tomáš Lébl, David B. Cordes, Alexandra M.Z. Slawin, Douglas Philp*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

Triphenylphosphine oxide forms halogen-bonded (XB) complexes with pentafluoroiodobenzene and a 1,4-diaryl-5-iodotriazole. The stability of these complexes is assessed computationally and by 31P NMR spectroscopy in toluene-d8 solution, where both complexes are weakly associated. This knowledge is applied to the design and synthesis of two self-complementary phosphine oxide-iodotriazole hybrids that incorporate a phosphine oxide XB acceptor and a 1,4-diphenyl-5-iodotriazole XB donor within the same molecule. The self-complementary design of these modules facilitates their assembly in both toluene-d8 and, surprisingly, DCM-d2 into dimers, with significant stabilities, through the formation of halogen-bonded diads. The stability of these assemblies is a result of significant levels of cooperative binding that is present in both solvents. The connection of two of these hybrid units together, using a flexible spacer, facilitates the aggregation of these modules in DCM-d2 solution, through halogen bonding, forming oligomeric assemblies.

Original languageEnglish (US)
Pages (from-to)1986-1995
Number of pages10
JournalJournal of Organic Chemistry
Volume82
Issue number4
DOIs
StatePublished - Feb 17 2017

ASJC Scopus subject areas

  • Organic Chemistry

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