A Hexa-peri-hexabenzocoronene Cyclophane: An Addition to the Toolbox for Molecular Electronics

Mark D. Watson, Frank Jäckel, Nikolai Severin, Jürgen P. Rabe, Klaus Müllen

Research output: Contribution to journalArticlepeer-review

104 Scopus citations

Abstract

Cyclophanes with the largest-to-date polycyclic aromatic hydrocarbon (hexa-peri-hexabenzocoronene, HBC) to be entrained in such a structural motif are reported. The two disks are covalently captured by intermolecular ring-closing olefin metathesis of dienes in good yield. DSC, optical microscopy, and WAXD show the new cyclophanes to self-assemble to thermotropic columnar liquid crystal mesophases similar to monomeric analogues. Solution spectroscopic studies reveal that the two disks within a single unit lie face-to-face, with a small average lateral offset. Self-assembly into two-dimensional crystals at a solid-liquid interface was visualized by STM, and the electrical properties of single molecules were assessed by scanning tunneling spectroscopy revealing a diode-like behavior which is similar to that previously reported for single HBC disks, laying the groundwork for future electrical interrogations of dynamic molecular complexes.

Original languageEnglish
Pages (from-to)1402-1407
Number of pages6
JournalJournal of the American Chemical Society
Volume126
Issue number5
DOIs
StatePublished - Feb 11 2004

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)
  • Biochemistry
  • Colloid and Surface Chemistry

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