Peralkylated Coronenes via Regiospecific Hydrogenation of Hexa-peri-hexabenzocoronenes

Mark D. Watson, Michael G. Debije, John M. Warman, Klaus Müllen

Research output: Contribution to journalArticlepeer-review

30 Scopus citations

Abstract

A remarkable, regiospecific hydrogenation zips around the ∼4 nm perimeter of hexa-perihexabenzocoronenes (HBC) adding 18 hydrogen atoms, leading to the first peralkylated coronenes, in quantitative yields in some cases. Increasing steric bulk of side chains was found to hinder the reaction, while unsubstituted HBC could be converted to a modest extent despite its vanishing solubility. The structures of the novel coronenes are unequivocally confirmed by MALDI-TOF, 1H, 13C, and heteronuclear correlation NMR, and UV-vis absorption spectroscopy. The puckered-ring periphery of these discotics does not prohibit self-assembly to columnar structures in a fashion similar to that of the planar precursors, as determined from wide-angle X-ray diffraction, but decreases the isotropization temperature by ∼300 °C relative to the latter. Branching in the alkyl chains frustrates nucleation from the melt, resulting in clear polymorphism depending on the thermal treatment. Nonetheless, preliminary measurements indicate high charge-carrier mobilities and lifetimes within the bulk material, on the same order as those previously found for HBCs.

Original languageEnglish
Pages (from-to)766-771
Number of pages6
JournalJournal of the American Chemical Society
Volume126
Issue number3
DOIs
StatePublished - Jan 28 2004

ASJC Scopus subject areas

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

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