Design and synthesis of new stable fluorenyl-based radicals

Yi Tian, Kazuyuki Uchida, Hiroyuki Kurata, Yasukazu Hirao, Tomohiko Nishiuchi, Takashi Kubo

    Research output: Contribution to journalArticlepeer-review

    48 Citations (Scopus)

    Abstract

    Organic neutral radicals have long fascinated chemists with a fundamental understanding of structure-reactivity relationships in organic reactions and with applications as new functional materials. However, the elusive nature of these radicals makes the synthesis, isolation, and characterization very challenging. In this work, the synthesis of three long-lived, fluorenyl-based radicals are reported. The geometry and electronic structures of these radicals were systematically investigated with a combination of various experimental methods, besides density functional theory (DFT) calculations, which include X-ray crystallographic analysis, electron spin resonance (ESR), electron nuclear double resonance (ENDOR), cyclic voltammetry, and UV-vis-NIR measurements. Their half-life periods (τ1/2) in air-saturated solution under ambient conditions were also determined. Surprisingly, all three radicals showed remarkable stabilities: τ1/2 = 7, 3.5, and 43 days.

    Original languageEnglish
    Pages (from-to)12784-12793
    Number of pages10
    JournalJournal of the American Chemical Society
    Volume136
    Issue number36
    DOIs
    Publication statusPublished - 2014 Sep 10

    ASJC Scopus subject areas

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

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