Please use this identifier to cite or link to this item: https://doi.org/10.1002/chem.201303868
Title: Meso-ester and carboxylic acid substituted BODIPYs with far-red and near-infrared emission for bioimaging applications
Authors: Ni, Y.
Zeng, L.
Kang, N.-Y.
Huang, K.-W.
Wang, L.
Zeng, Z.
Chang, Y.-T. 
Wu, J. 
Keywords: bioimaging
BODIPY
dyes
fluorescent probes
membrane permeability
near-infrared
Issue Date: 17-Feb-2014
Citation: Ni, Y., Zeng, L., Kang, N.-Y., Huang, K.-W., Wang, L., Zeng, Z., Chang, Y.-T., Wu, J. (2014-02-17). 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. ScholarBank@NUS Repository. https://doi.org/10.1002/chem.201303868
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.
Source Title: Chemistry - A European Journal
URI: http://scholarbank.nus.edu.sg/handle/10635/94201
ISSN: 09476539
DOI: 10.1002/chem.201303868
Appears in Collections:Staff Publications

Show full item record
Files in This Item:
There are no files associated with this item.

SCOPUSTM   
Citations

30
checked on Dec 14, 2018

WEB OF SCIENCETM
Citations

31
checked on Nov 21, 2018

Page view(s)

43
checked on Nov 9, 2018

Google ScholarTM

Check

Altmetric


Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.