The idiosyncrasies of tetrabenzo[24]crown-8 in the solid state

Stuart J. Cantrill, Jon A. Preece, J. Fraser Stoddart*, Zhen He Wang, Andrew J P White, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

In the solid state, the macrocyclic polyether tetrabenzo[24]crown-8 (TB24C8) is an interesting molecule. When crystallized from MeCN solution, a bis-MeCN clathrate is formed, in which the TB24C8 macroring - by adopting a conformation with approximate tenms-ball-seam symmetry (D(2d)) - forms C-H···π-linked supramolecular chains. However, when crystallized from CHCl3/Et2O solution, the TB24C8 crystallizes alone - adopting a self-filling 'flattened-out' conformation with C(i) symmetry - forming C-H···π-linked sheets which stack upon one another by virtue of - yet again (!) - C-H···π hydrogen bonds. By contrast, the solid-state superstructure of the [2]pseudorotaxane formed between TB24C8 and dibenzylammonium hexafluorophosphate (DBA.PF6), contains no C-H···π interactions. However, a multitude of more enthalpically favorable C-H···F hydrogen bonds - to a highly-ordered matrix of PF6 anions - stabilizes the formation of the [2]pseudorotaxane array. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)6675-6681
Number of pages7
JournalTetrahedron
Volume56
Issue number36
DOIs
StatePublished - Jan 1 2000

Keywords

  • C-H···π interactions
  • Crown ethers
  • Hydrogen bonding
  • Pseudo-rotaxanes
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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