Catalytic Enantioselective Synthesis of Axially Chiral Polycyclic Aromatic Hydrocarbons (PAHs) via Regioselective C-C Bond Activation of Biphenylenes

Hideaki Takano, Natsumi Shiozawa, Yoshitane Imai, Kyalo Stephen Kanyiva, Takanori Shibata

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

Chiral polycyclic aromatic hydrocarbons (PAHs) are expected to have unusual physical properties due to their chirality and expanded π-conjugated system. Indeed, PAHs are promising compounds as chiral recognizers and organic semiconductors. Therefore, an efficient method for the synthesis of chiral PAHs is strongly desired. In contrast to helically chiral PAHs, there are only limited examples of the enantioselective synthesis of axially chiral PAHs. Herein, we report the catalytic enantioselective synthesis of benzo[b]fluoranthene-based axially chiral PAHs in excellent yields and enantioselectivities (up to >99%, >99% ee) by regioselective cleavage of the sterically hindered C-C bond of biphenylenes. The consecutive cyclizations could provide polycyclic PAHs with two chiral axes. The obtained chiral PAHs have high ϵ values (up to ϵ = 8.9 × 104), quantum yields (up to φ = 0.67), and circularly polarized luminescence (CPL) property (|glum| = up to 3.5 × 10-3).

Original languageEnglish
Pages (from-to)4714-4722
Number of pages9
JournalJournal of the American Chemical Society
Volume142
Issue number10
DOIs
Publication statusPublished - 2020 Mar 11

ASJC Scopus subject areas

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

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