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    Super-heptazethrene

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    Type
    Article
    Authors
    Zeng, Wangdong
    Sun, Zhe
    Herng, Tun Seng
    Goncalves, Theo
    Gopalakrishna, Tullimilli Y.
    Huang, Kuo-Wei cc
    Ding, Jun
    Wu, Jishan
    KAUST Department
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2016-05-30
    Online Publication Date
    2016-05-30
    Print Publication Date
    2016-07-18
    Permanent link to this record
    http://hdl.handle.net/10754/623144
    
    Metadata
    Show full item record
    Abstract
    The challenging synthesis of a laterally extended heptazethrene molecule, the super-heptazethrene derivative SHZ-CF3, is reported. This molecule was prepared using a strategy involving a multiple selective intramolecular Friedel–Crafts alkylation followed by oxidative dehydrogenation. Compound SHZ-CF3 exhibits an open-shell singlet diradical ground state with a much larger diradical character compared with the heptazethrene derivatives. An intermediate dibenzo-terrylene SHZ-2H was also obtained during the synthesis. This study provides a new synthetic method to access large-size quinoidal polycyclic hydrocarbons with unique physical properties.
    Citation
    Zeng W, Sun Z, Herng TS, Gonçalves TP, Gopalakrishna TY, et al. (2016) Super-heptazethrene. Angewandte Chemie International Edition 55: 8615–8619. Available: http://dx.doi.org/10.1002/anie.201602997.
    Sponsors
    This work was supported by the MOE Tier 3 programme (MOE2014-T3-1-004) and by an A*STAR JCO grant (1431AFG100). We thank Dr. Hiroyasu Sato in Rigaku Co. and Dr. Bruno Donnadieu in NUS for the crystallographic analysis.
    Publisher
    Wiley-Blackwell
    Journal
    Angewandte Chemie International Edition
    DOI
    10.1002/anie.201602997
    10.1002/ange.201602997
    ae974a485f413a2113503eed53cd6c53
    10.1002/anie.201602997
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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