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dc.contributor.authorNi, Yong
dc.contributor.authorZeng, Lintao
dc.contributor.authorKang, Namyoung
dc.contributor.authorHuang, Kuo-Wei
dc.contributor.authorWang, Liang
dc.contributor.authorZeng, Zebing
dc.contributor.authorChang, Young-Tae
dc.contributor.authorWu, Jishan
dc.date.accessioned2015-08-03T11:46:18Z
dc.date.available2015-08-03T11:46:18Z
dc.date.issued2014-01-21
dc.identifier.issn09476539
dc.identifier.doi10.1002/chem.201303868
dc.identifier.urihttp://hdl.handle.net/10754/563346
dc.description.abstractA 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.
dc.description.sponsorshipThe 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).
dc.publisherWiley
dc.subjectbioimaging
dc.subjectBODIPY
dc.subjectdyes
dc.subjectfluorescent probes
dc.subjectmembrane permeability
dc.subjectnear-infrared
dc.titleMeso-ester and carboxylic acid substituted BODIPYs with far-red and near-infrared emission for bioimaging applications
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentHomogeneous Catalysis Laboratory (HCL)
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalChemistry - A European Journal
dc.contributor.institutionDepartment of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
dc.contributor.institutionNUS Environmental Research Institute, National University of Singapore, 5A Engineering Drive 1, 02-01, Singapore 117411, Singapore
dc.contributor.institutionSchool of Chemical and Chemical Engineering, Tianjin University of Technology, Tianjin 300384, China
dc.contributor.institutionLaboratory of Bioimaging Probe Development, Singapore Bioimaging Consortium, ASTAR, Singapore
dc.contributor.institutionInstitute of Materials Research and Engineering, ASTAR, 3 Research Link, Singapore 117602, Singapore
kaust.personHuang, Kuo-Wei
dc.date.published-online2014-01-21
dc.date.published-print2014-02-17


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