Self-assembly of grid and helical hydrogen-bonded arrays incorporating bowl-shaped receptor sites that bind globular molecules

Michaele J. Hardie, Peter D. Godfrey, Colin L. Raston

Research output: Contribution to journalArticle

93 Citations (Scopus)

Abstract

1,2-Dicarbadodecaborane(12) (o-carborane) and bowl-shaped cyclotriveratrylene (CTV) self-assemble through bifurcated C-Hcarborane ⋯ (O)2 hydrogen bonds into infinite arrays with two-dimensional (2D) hexagonal grid or helical chain topologies. The in-built shape-specific receptor sites bind o-carborane or fullerene C70. The structures of two such supramolecular systems in the solid state were established: (o-carborane)2(CTV) features hydrogenbonded carborane ⋯ CTV hexagonal grids as well as CTV ⋯ carborane host-guest interactions, while a helical hydrogen-bonded carborane ⋯ CTV chain is formed in the quaternary system (C70)(o-carborane)(CTV)(1,2-dichlorobenzene) in addition to CTV ⋯ C70 host-guest interactions. The bifurcated C-Hcarborane ⋯ (O)2 hydrogen bonding interaction common to both these structures was studied on the model system (o-carborane)(1,2-dimethoxybenzene) using ab initio calculations and found to be energetically favoured by 5.48 kcal mol-1, whereas a B-Hcarborane ⋯ (O), bifurcated hydrogen bonding was less favoured at 1.13 kcal mol-1.

Original languageEnglish
Pages (from-to)1828-1833
Number of pages6
JournalChemistry - A European Journal
Volume5
Issue number6
DOIs
Publication statusPublished - 1 Jan 1999
Externally publishedYes

Keywords

  • Ab initio calculations
  • Carboranes
  • Crystal engineering
  • Fullerenes
  • Host-guest chemistry

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