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    Meso-ester and carboxylic acid substituted BODIPYs with far-red and near-infrared emission for bioimaging applications

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    Type
    Article
    Authors
    Ni, Yong
    Zeng, Lintao
    Kang, Namyoung
    Huang, Kuo-Wei cc
    Wang, Liang
    Zeng, Zebing
    Chang, Young-Tae
    Wu, Jishan
    KAUST Department
    Chemical Science Program
    Homogeneous Catalysis Laboratory (HCL)
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2014-01-21
    Online Publication Date
    2014-01-21
    Print Publication Date
    2014-02-17
    Permanent link to this record
    http://hdl.handle.net/10754/563346
    
    Metadata
    Show full item record
    Abstract
    A series of meso-ester-substituted BODIPY derivatives 1-6 are synthesized and characterized. In particular, dyes functionalized with oligo(ethylene glycol) ether styryl or naphthalene vinylene groups at the α positions of the BODIPY core (3-6) become partially soluble in water, and their absorptions and emissions are located in the far-red or near-infrared region. Three synthetic approaches are attempted to access the meso-carboxylic acid (COOH)-substituted BODIPYs 7 and 8 from the meso-ester-substituted BODIPYs. Two feasible synthetic routes are developed successfully, including one short route with only three steps. The meso-COOH-substituted BODIPY 7 is completely soluble in pure water, and its fluorescence maximum reaches around 650 nm with a fluorescence quantum yield of up to 15 %. Time-dependent density functional theory calculations are conducted to understand the structure-optical properties relationship, and it is revealed that the Stokes shift is dependent mainly on the geometric change from the ground state to the first excited singlet state. Furthermore, cell staining tests demonstrate that the meso-ester-substituted BODIPYs (1 and 3-6) and one of the meso-COOH-substituted BODIPYs (8) are very membrane-permeable. These features make these meso-ester- and meso-COOH-substituted BODIPY dyes attractive for bioimaging and biolabeling applications in living cells. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
    Citation
    Ni, Y., Zeng, L., Kang, N.-Y., Huang, K.-W., Wang, L., Zeng, Z., … Wu, J. (2014). meso-Ester and Carboxylic Acid Substituted BODIPYs with Far-Red and Near-Infrared Emission for Bioimaging Applications. Chemistry - A European Journal, 20(8), 2301–2310. doi:10.1002/chem.201303868
    Sponsors
    The work was supported financially by the A*STAR BMRC grant (10/1/21/19/642), the Singapore-Peking-Oxford Research Enterprise (SPORE) (COY-15-EWI-RCFSA/N197-1), MOE Tier 2 grant (MOE2011-T2-2-130), and IMRE core funding (IMRE/13-1C0205).
    Publisher
    Wiley
    Journal
    Chemistry - A European Journal
    DOI
    10.1002/chem.201303868
    ae974a485f413a2113503eed53cd6c53
    10.1002/chem.201303868
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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