“π-Hole−π” Interaction Promoted Photocatalytic Hydrodefluorination via Inner-Sphere Electron Transfer

Jingzhi Lu, Navneet S. Khetrapal, Jacob A. Johnson, Xiao Cheng Zeng, Jian Zhang

Research output: Contribution to journalArticle

20 Scopus citations

Abstract

We describe a metal-free, photocatalytic hydrodefluorination (HDF) of polyfluoroarenes (FA) using pyrene-based photocatalysts (Py). The weak “π-hole−π” interaction between Py and FA promotes the electron transfer against unfavorable energetics (ΔGET up to 0.63 eV) and initiates the subsequent HDF. The steric hindrance of Py and FA largely dictates the HDF reaction rate, pointing to an inner-sphere electron transfer pathway. This work highlights the importance of the size and shape of the photocatalyst and the substrate in controlling the electron transfer mechanism and rates as well as the overall photocatalytic processes.

Original languageEnglish (US)
Pages (from-to)15805-15808
Number of pages4
JournalJournal of the American Chemical Society
Volume138
Issue number49
DOIs
StatePublished - Dec 14 2016

ASJC Scopus subject areas

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

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