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    Lateral extension of π conjugation along the bay regions of bisanthene through a diels-alder cycloaddition reaction

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    Type
    Article
    Authors
    Li, Jinling
    Jiao, Chongjun
    Huang, Kuo-Wei cc
    Wu, Jishan
    KAUST Department
    Biological and Environmental Sciences and Engineering (BESE) Division
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2011-11-14
    Online Publication Date
    2011-11-14
    Print Publication Date
    2011-12-16
    Permanent link to this record
    http://hdl.handle.net/10754/561920
    
    Metadata
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    Abstract
    Diels-Alder cycloaddition reactions at the bay regions of bisanthene (1) with dienophiles such as 1,4-naphthoquinone have been investigated. The products were submitted to nucleophilic addition followed by reductive aromatization reactions to afford the laterally extended bisanthene derivatives 2 and 3. Attempted synthesis of a larger expanded bisanthene 4 revealed an unexpected hydrogenation reaction at the last reductive aromatization step. Unusual Michael addition was observed on quinone 14, which was obtained by Diels-Alder reaction between 1 and 1,4-anthraquinone. Compounds 1-3 exhibited near-infrared (NIR) absorption and emission with high-to-moderate fluorescent quantum yields. Their structures and absorption spectra were studied by density function theory and non-planar twisted structures were calculated for 2 and 3. All compounds showed amphoteric redox behavior with multiple oxidation/reduction waves. Oxidative titration with SbCl 5 gave stable radical cations, and the process was followed by UV/Vis/NIR spectroscopic measurements. Their photostability was measured and correlated to their different geometries and electronic structures. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Citation
    Li, J., Jiao, C., Huang, K.-W., & Wu, J. (2011). Lateral Extension of π Conjugation along the Bay Regions of Bisanthene through a Diels-Alder Cycloaddition Reaction. Chemistry - A European Journal, 17(51), 14672–14680. doi:10.1002/chem.201102120
    Sponsors
    J. W. acknowledges financial support from Singapore DSTA DIRP Project (DSTA-NUS-DIRP/2008/03), the NRF Competitive Research Program (R-143-000-360-281), and A*Star BMRC grant (No. 10/1/21/19/642). K.-W. H. acknowledges financial support from KAUST.
    Publisher
    Wiley
    Journal
    Chemistry - A European Journal
    DOI
    10.1002/chem.201102120
    PubMed ID
    22083876
    ae974a485f413a2113503eed53cd6c53
    10.1002/chem.201102120
    Scopus Count
    Collections
    Articles; Biological and Environmental Sciences and Engineering (BESE) Division; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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