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Bichromophoric fluorescent photolabile protecting group for alcohols and carboxylic acids

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Abstract

Novel bichromophoric fluorescent photolabile protecting group, (5-dansyloxy-3-hydroxynaphthalen-2-yl)methyl (DNS-NQMP), allows for the independent photochemical release and fluorescent imaging of caged substrates. Irradiation of DNS-NQMP-caged alcohols and carboxylic acids with 300 or 350 nm light results in fast (krelease ~ 105 s-1), efficient (Φ = 0.2), and quantitative release of the substrates. This uncaging chemistry is compatible with aqueous media and DNS-NQMP-protected hydroxy compounds are hydrolytically stable at neutral pH. Upon excitation with 400 nm light, caged compounds show intense green emission (λmax = 559 nm) with 21% fluorescence quantum yield. Fluorescent readout conducted using 400 nm or longer wavelengths does not cause substrate release. The DNS-NQMP chromophore retains its fluorescent properties after photo-uncaging reaction.

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Authors and Affiliations

  1. Department of Chemistry, University of Georgia, Athens, Georgia, 30602, USA

    Selvanathan Arumugam & Vladimir V. Popik

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  1. Selvanathan Arumugam
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  2. Vladimir V. Popik
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Correspondence to Vladimir V. Popik.

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Arumugam, S., Popik, V.V. Bichromophoric fluorescent photolabile protecting group for alcohols and carboxylic acids. Photochem Photobiol Sci 11, 518–521 (2012). https://doi.org/10.1039/c1pp05317e

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  • DOI: https://doi.org/10.1039/c1pp05317e

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