Unusual molecular conformations in fluorinated, contorted hexabenzocoronenes

Yueh Lin Loo, Anna M. Hiszpanski, Bumjung Kim, Sujun Wei, Chien Yang Chiu, Michael L. Steigerwald, Colin Nuckolls

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Abstract

Fluorinated, contorted hexabenzocoronenes (HBCs) have been synthesized in a facile manner via Suzuki-Miyaura coupling of fluorinated phenyl boronic acids followed by photocyclization and Scholl cyclization. In addition to the molecular conformation observed in previous HBC derivatives, close-contact fluorine-fluorine intramolecular interactions result in a metastable conformation not previously observed. Heating the metastable HBCs above 100 °C irreversibly converts them to the stable conformation, suggesting that the metastable conformation arises from a kinetically arrested state during cyclization.

Original languageEnglish (US)
Pages (from-to)4840-4843
Number of pages4
JournalOrganic Letters
Volume12
Issue number21
DOIs
StatePublished - Nov 5 2010

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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    Loo, Y. L., Hiszpanski, A. M., Kim, B., Wei, S., Chiu, C. Y., Steigerwald, M. L., & Nuckolls, C. (2010). Unusual molecular conformations in fluorinated, contorted hexabenzocoronenes. Organic Letters, 12(21), 4840-4843. https://doi.org/10.1021/ol102016m