Symmetry-aligned supramolecular encapsulation of C60: [C60 ⊂ (L)2], L =p-benzylcalix[5]arene or p-benzylhexahomooxacalix[3]arene

Jerry L. Atwood, Leonard J. Barbour, Peter J. Nichols, Colin L. Raston, Christian A. Sandoval

Research output: Contribution to journalArticle

101 Citations (Scopus)

Abstract

p-Benzylcalix[5]arene (1) or p-benzylhexahomooxacalix[3]arene (2) form 2:1 complexes with C60 in solutions of the fullerene or fullerite in toluene to give [C60 ⊂ (1)2] · 8toluene and [C60 ⊂ (2)2], respectively. In both structures the fullerene is shrouded by two staggered, trans-disposed, host molecules. These host calixarenes adopt a cone conformation and the benzyl groups are either dangling ([C60 ⊂ (1)2] · 8toluene) or they are positioned edge-on to the fullerene ([C60 ⊂ (2)2]). The alignment of the symmetry axis of the calixarene, C5 or C3, respectively, with the same symmetry element of C60 highlights the importance of symmetry matching in the design of host molecules for fullerenes, as it maximises the number of points of contact and the efficiency of the π⋯π interactions. Two host-guest associations for 1 and 2 with C60 are evident in solutions in toluene. The new oxacalix[3]arene 2 crystallises with chloroform as the 1:1 complex [CHCl3 ⊂ (2)].

Original languageEnglish
Pages (from-to)990-996
Number of pages7
JournalChemistry - A European Journal
Volume5
Issue number3
DOIs
Publication statusPublished - 1 Dec 1999
Externally publishedYes

Keywords

  • Calixarenes
  • Fullerenes
  • Host-guest chemistry
  • Inclusion compounds
  • Supramolecular chemistry

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