New insights into the hexaphenylethane riddle: Formation of an α,o-dimer

Yasuto Uchimura, Takashi Takeda, Ryo Katoono, Kenshu Fujiwara, Takanori Suzuki

    Research output: Contribution to journalArticlepeer-review

    15 Citations (Scopus)

    Abstract

    Upon reduction of a 1H-cyclobuta[de]naphthalene-4,5-diylbis(diarylmethylium) species, a new C-C bond is formed between the Cα and Cortho atoms of the two chromophores, which presents an unprecedented coupling pattern for the dimerization of two trityl units. By attaching an annulated cyclobutane ring at the opposite peri position of the naphthalene core, the distance between the Cα carbon atoms was elongated beyond the limit of σ-bond formation through "scissor effects". The suppression of Cα-Cα bond formation, which would lead to hexaphenylethane-type compounds, is key to the first successful isolation of the α,o-adducts. The 5-diarylmethylene-6-triarylmethyl-1,3-cyclohexadiene unit in the α,o-adducts is stable, and isomerization of the cyclohexadiene unit into an aromatic system was not observed. The newly formed Cα-Cortho bond was cleaved upon two-electron oxidation to regenerate the dicationic dye.

    Original languageEnglish
    Pages (from-to)4010-4013
    Number of pages4
    JournalAngewandte Chemie - International Edition
    Volume54
    Issue number13
    DOIs
    Publication statusPublished - 2015 Mar 23

    Keywords

    • X-ray diffraction
    • dimerization
    • radicals
    • steric hindrance
    • strained molecules

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)

    Fingerprint

    Dive into the research topics of 'New insights into the hexaphenylethane riddle: Formation of an α,o-dimer'. Together they form a unique fingerprint.

    Cite this