Influence of hydrogen bonds on the supramolecular order of hexa-peri-hexabenzocoronenes

Daniel Wasserfallen, Ingrid Fischbach, Natalia Chebotareva, Marcel Kastler, Wojciech Pisula, Frank Jäckel, Mark D. Watson, Ingo Schnell, Jürgen P. Rabe, Hans W. Spiess, Klaus Müllen

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62 Scopus citations


Three different hexa-peri-hexabenzocoronene (HBC) derivatives with carboxylic acid functions have been synthesized to study the effect of hydrogen bonding on the already pronounced columnar it-stacking. This functionalization improves the degree of order in the bulk and influences the surface patterning at solid-liquid interfaces as well as the thermal properties of these materials. The length of the tether between the aromatic core and the hydrogen-bond- forming carboxy group appears as a key factor influencing the supramolecular self-assembly, since only the HBCs with shorter spacers showed a strong synergetic effect of the columnar π-stacking with the hydrogen-bonding motifs. Clear signatures for this are unusually high mesophase transition temperatures and non-tilted columnar stacking in the pseudocrystalline phase. As model systems, HBC dyads have been synthesized with the two HBC disks linked through a covalent spacer fitting the intercolumnar distance of the short-tethered, hydrogen-bridged dimer. This comparison emphasized the impact of the hydrogen bonds on the supramolecular properties of the materials. A broad range of analytical methods have been used, including differential scanning calorimetry, wide-angle X-ray diffractometry, solid-state NMR spectroscopy, and scanning tunneling microscopy.

Original languageEnglish
Pages (from-to)1585-1594
Number of pages10
JournalAdvanced Functional Materials
Issue number10
StatePublished - Oct 2005

ASJC Scopus subject areas

  • Chemistry (all)
  • Materials Science (all)
  • Condensed Matter Physics


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