Journal
TETRAHEDRON LETTERS
Volume 55, Issue 51, Pages 7124-7129Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2014.11.004
Keywords
Absorption; Fluorescence; Boron; Suzuki-Miyaura coupling; Singlet-oxygen generation
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Funding
- Department of Science and Technology, India [SR/FT/CS-87/2010]
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Mono and di-heteroary1-4,4'-difluoro-8-(aryl)-4-bora-3a,4a-diaza-s-indacene (BODIPy) (1-5) were synthesized using Suzuki-Miyaura couplings. Hetero aryl substitution on 3- or 3,5-positions caused large bathochromic shifts (up to similar to 150 nm) in absorption (569-652 rim) and fluorescence maxima (586-679 nm) in comparison to classical BODIPy. Quantum yields were found to be as high as 0.65. Singlet oxygen production activities of these compounds were studied by monitoring the absorbance quenching of 1,3-diphenylisobenzofuran, on exposure to light (>600 nm). Cellular uptake of compound 4 was demonstrated using cervical cancer cells and fibroblast cell line and was confirmed by the images obtained using confocal microscope. (C) 2014 Elsevier Ltd. All rights reserved.
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