Meso-ester and carboxylic acid substituted BODIPYs with far-red and near-infrared emission for bioimaging applications
Type
ArticleAuthors
Ni, YongZeng, Lintao
Kang, Namyoung
Huang, Kuo-Wei

Wang, Liang
Zeng, Zebing
Chang, Young-Tae
Wu, Jishan
KAUST Department
Chemical Science ProgramHomogeneous Catalysis Laboratory (HCL)
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2014-01-21Online Publication Date
2014-01-21Print Publication Date
2014-02-17Permanent link to this record
http://hdl.handle.net/10754/563346
Metadata
Show full item recordAbstract
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.201303868Sponsors
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
WileyJournal
Chemistry - A European Journalae974a485f413a2113503eed53cd6c53
10.1002/chem.201303868