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    Palladium-Catalyzed Direct C-H Arylations of Dioxythiophenes Bearing Reactive Functional Groups: A Step-Economical Approach for Functional π-Conjugated Oligoarenes

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    C5OB00705D.pdf
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    PDF
    Description:
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    Type
    Article
    Authors
    Liu, Ching-Yuan
    Chong, Hui
    Lin, Hsing-An
    Yamashita, Yoshiro
    Zheng, Bin cc
    Huang, Kuo-Wei cc
    Hashizume, Daisuke
    Yu, Hsiao-hua
    KAUST Department
    Analytical Chemistry Core Lab
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    Imaging and Characterization Core Lab
    KAUST Catalysis Center (KCC)
    Nanofabrication Core Lab
    Physical Science and Engineering (PSE) Division
    Date
    2015
    Permanent link to this record
    http://hdl.handle.net/10754/558679
    
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    Abstract
    A Pd-catalyzed and single-step C-H arylation of dioxythiophene derivates bearing unprotected reactive functional groups (-OH, -COOH, -N3) in a phosphine-free manner has been developed. Various dioxythiopene-based oligoarenes with extended π-conjugation are obtained with good yields (up to 90%). These oligoarenes display suitable optical properties (absorption and emission maxima, quantum yields) and contain reactive functional groups suitable for further conjugations with bioactive molecules. This new methodology is step economical (fewer synthetic steps), environmental friendly (no toxic metal-containing side-poducts) and the oligoarenes synthesized are potentially applicable for bio-labeling, bioimaging, and biosensing.
    Citation
    Palladium-Catalyzed Direct C-H Arylations of Dioxythiophenes Bearing Reactive Functional Groups: A Step-Economical Approach for Functional π-Conjugated Oligoarenes 2015 Org. Biomol. Chem.
    Publisher
    Royal Society of Chemistry (RSC)
    Journal
    Organic & Biomolecular Chemistry
    DOI
    10.1039/C5OB00705D
    Additional Links
    http://pubs.rsc.org/en/Content/ArticleLanding/2015/OB/C5OB00705D
    Relations
    Is Supplemented By:
    • [Dataset]
      Liu, C.-Y., Chong, H., Lin, H.-A., Yamashita, Y., Zhang, B., Huang, K.-W., … Yu, H.-H. (2015). CCDC 1055679: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14fj58. DOI: 10.5517/cc14fj58 HANDLE: 10754/624421
    • [Dataset]
      Liu, C.-Y., Chong, H., Lin, H.-A., Yamashita, Y., Zhang, B., Huang, K.-W., … Yu, H.-H. (2015). CCDC 1055680: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14fj69. DOI: 10.5517/cc14fj69 HANDLE: 10754/624422
    • [Dataset]
      Liu, C.-Y., Chong, H., Lin, H.-A., Yamashita, Y., Zhang, B., Huang, K.-W., … Yu, H.-H. (2015). CCDC 1055681: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc14fj7b. DOI: 10.5517/cc14fj7b HANDLE: 10754/624423
    ae974a485f413a2113503eed53cd6c53
    10.1039/C5OB00705D
    Scopus Count
    Collections
    Nanofabrication Core Lab; Articles; Analytical Chemistry Core Lab; Imaging and Characterization Core Lab; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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