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    Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10259/4880

    Título
    1,8-Diamidocarbazoles: an easily tuneable family of fluorescent anion sensors and transporters
    Autor
    Bąk, Krzysztof M. .
    Chabuda, Krzysztof .
    Montes Andrés, HelenaUBU authority
    Quesada Pato, RobertoUBU authority Orcid
    Chmielewski, Michał J.
    Publicado en
    Organic & Biomolecular Chemistry. 2018, V. 16, n. 28, p. 5188-5196
    Editorial
    Royal Society of Chemistry
    Fecha de publicación
    2018-07
    ISSN
    1477-0520
    DOI
    10.1039/C8OB01031E
    Abstract
    The synthesis, structure and anion recognition properties of an extensive, rationally designed series of bisamide derivatives of 1,8-diaminocarbazole and 1,8-diamino-3,6-dichlorocarbazole are described. Despite simple structures and the presence of only three hydrogen bond donors, such compounds are remarkably strong and selective receptors for oxyanions in DMSO + 0.5%H2O. Owing to their carbazole fluorophore, they are also sensitive turn-on fluorescent sensors for H2PO4− and AcO−, with a more than 15-fold increase in fluorescence intensity upon binding. Despite relatively weak chloride affinity, some of the diamidocarbazoles have also been shown, for the first time, to be very active chloride transporters through lipid bilayers. The binding, sensing and transport properties of these receptors can be easily modulated by the usually overlooked variations in the length and degree of branching of their alkyl side arms. Overall, this study demonstrates that the 1,8-diamidocarbazole binding unit is a very promising and synthetically versatile platform for the development of fluorescent sensors and transporters for anions.
    Materia
    Química orgánica
    Chemistry, Organic
    URI
    http://hdl.handle.net/10259/4880
    Versión del editor
    https://doi.org/10.1039/C8OB01031E
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    • Artículos BIOORG
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