Molecular and supramolecular synthesis with dibenzofuran-containing systems

Masumi Asakawa, Peter R. Ashton, Christopher L. Brown, Matthew C T Fyfe, Stephan Menzer, Dario Pasini, Cecile Scheuer, Neil Spencer, J. Fraser Stoddart, Andrew J P White, David J. Williams

Research output: Contribution to journalArticlepeer-review

44 Scopus citations


The template-directed syntheses of two new tetracationic cyclophanes, cyclobis(paraquat-2,8-dibenzofuran) and cyclobis(paraquat-3,7-dibenzofuran), incorporating dibenzofuran subunits has been accomplished. Initially, the cyclophanes were self-assembled around a macrocyclic polyether template, bis-p-phenylene[34]crown-10 (BPP34C10), to form catenanes: the mechanical bond order of the catenane formed determined the requisite 'amacrocyclic' templates for synthesis of the free cyclophane. X-ray crystallography shows that both of the cyclophanes possess rectangular covalent frameworks. Furthermore, these cyclophanes form self-assembled tapes in the solid state, since the dibenzofuran moieties have a tendency to associate with each other through crossed π-π stacks. The dibenzofuran-containing catenanes also form two-dimensional supramolecular arrays in the solid state on account of extended π-π stacking interactions. In addition, the serendipitous discovery of a plerotopic tecton (consisting of a dibenzofuran nucleus covalently linked from the 2- and 8-positions by methylene groups to 4,4'-pyridylpyridinium (hydrogen bond acceptor) and protonated bipyridinium (hydrogen bond donor) units) has been made. The tecton dimerizes in the solid state to form a supramolecular macrocycle, since its complementary hydrogen bonding sites are oriented in a horseshoe-like fashion by the 2.8-disubstituted dibenzofuran unit. However, this superstructure is not retained in the 1:1 complex of the tecton with BPP34C10: cocrystallization of the tecton with this crown ether opens the macrocylic two-component supermolecule to afford a hydrogen-bonded pseudopolyrotaxane.

Original languageEnglish (US)
Pages (from-to)1136-1150
Number of pages15
JournalChemistry - A European Journal
Issue number7
StatePublished - Jan 1 1997


  • Crystal engineering
  • Dibenzofuran
  • Molecular quadrilaterals
  • Supramolecular chemistry
  • Template synthesis

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Organic Chemistry


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