Ordered architectures of a soluble hexa-peri-hexabenzocoronene-pyrene dyad: Thermotropic bulk properties and nanoscale phase segregation at surfaces

Natalia Tchebotareva, Xiaomin Yin, Mark D. Watson, Paolo Samorì, Jürgen P. Rabe, Klaus Müllen

Research output: Contribution to journalArticlepeer-review

80 Scopus citations

Abstract

An alkylated hexa-peri-hexabenzocoronene with a covalently tethered pyrene unit serves as a model to study self-assembling discotic π-system dyads both in the bulk and at a surface. Wide-angle X-ray scattering, polarized light microscopy, and differential scanning calorimetry revealed bulk self-assembly into columnar structures. Relative to a control without a tethered pyrene, the new dyad exhibits a more ordered columnar phase at room temperature but with dramatically lowered isotropization temperature, facilitating homeotropic alignment. These two features are important for processing such materials into molecular electronic devices, e.g., photovoltaic diodes. Scanning tunneling microscopy at a solution-solid interface revealed uniform nanoscale segregation of the large from the small π-systems, leading to a well-defined two-dimensional crystalline monolayer, the likes of which may be employed in the future to study intramolecular electron transfer processes at surfaces, on the molecular scale.

Original languageEnglish
Pages (from-to)9734-9739
Number of pages6
JournalJournal of the American Chemical Society
Volume125
Issue number32
DOIs
StatePublished - Aug 13 2003

ASJC Scopus subject areas

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

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