RT info:eu-repo/semantics/article
T1 1,8-Diamidocarbazoles: an easily tuneable family of fluorescent anion sensors and transporters
A1 Bąk, Krzysztof M. .
A1 Chabuda, Krzysztof .
A1 Montes Andrés, Helena
A1 Quesada Pato, Roberto
A1 Chmielewski, Michał J.
K1 Química orgánica
K1 Chemistry, Organic
AB 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.
PB Royal Society of Chemistry
SN 1477-0520
YR 2018
FD 2018-07
LK http://hdl.handle.net/10259/4880
UL http://hdl.handle.net/10259/4880
LA eng
NO Polish National Science Centre for grant OPUS(2011/01/B/ST5/03900). The study was carried out at theBiological and Chemical Research Centre, University of Warsaw,established within a project co-financed by the European Unionthrough the European Regional Development Fund under theOperational Programme Innovative Economy 2007–2013. R. Q.thanks financial support provided by Consejería de Educación –Junta de Castilla y León (Project BU092U16)
DS Repositorio Institucional de la Universidad de Burgos
RD 25-abr-2024