Self-assembly and self-organization of self-recognizing cyclophanes

Peter R. Ashton, Alexandre Chemin, Christian G. Claessens, Stephan Menzer, J. Fraser Stoddart*, Andrew J P White, David J. Williams

*Corresponding author for this work

Research output: Contribution to journalArticle

19 Scopus citations

Abstract

An analysis is presented of the different contributions that give rise to the packing observed in the crystal structures of a wide range of bipyridinium-based molecular assemblies and supramolecular arrays. It is demonstrated how the various interactions - electrostatic, van der Waals, and π-π interactions - that contribute to the solid-state arrangement of these molecules and supermolecules can be utilized in order to design a series of tetracationic cyclophanes that can potentially self-organize in a highly ordered way in the solid state by virtue of the fact that they contain π-electron donors as well as π-electron acceptors. The syntheses of these cyclophanes is outlined and the tunability of the self-assembly methodology in their construction is demonstrated. One of these tetracationic cyclophanes - comprising π-electron-rich hydroquinone rings and π-electron-deficient bipyridinium units - has been shown to pack as highly ordered two-dimensional, mosaic-like sheets in the solid state. Its dicationic precursor also forms extended π-π-stacked layers in the solid state. An analogous cyclophane - containing two π-electron-rich resorcinol rings in place of the two hydroquinone rings - forms, in the solid state, one-dimensional arrays wherein the component resorcinol rings interact through then: parallel π-π stacking. It has also been established that the first of the aforementioned tetracationic cyclophanes forms a 1:1 adduct with ferrocene in both the solution and solid states. X-ray crystallography, performed on the 1:1 adduct, reveals that not only is the ferrocene molecule complexed in a π-π slacking sense within the tetracationic cyclophane, but the 1:1 adduct also packs in a manner that is remarkably similar to the supramolecular organization of the free cyclophane in the crystalline state.

Original languageEnglish (US)
Pages (from-to)969-981
Number of pages13
JournalEuropean Journal of Organic Chemistry
Issue number6
DOIs
StatePublished - Jun 1998

Keywords

  • Crystal engineering
  • Host-guest chemistry
  • Nanotubes
  • Sandwich complexes
  • Self-assembly

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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