2026-04-28T20:47:56Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/48802022-12-20T11:47:51Zcom_10259_3924com_10259_5086com_10259_2604col_10259_3925

Bąk, Krzysztof M. . c7352276-da10-4a20-be61-a2c44fc96858 500 Chabuda, Krzysztof . ce786315-c0d8-4803-aad7-8bb6eaa46c7a 500 Montes Andrés, Helena 373 600 Quesada Pato, Roberto 458 500 0000-0003-2764-7157 Chmielewski, Michał J. f360d809-8ef4-43bb-badf-d9d16fa36c5a 500 2018-08-24T08:25:20Z 2019-07-28T02:45:07Z 2018-07 1477-0520 http://hdl.handle.net/10259/4880 10.1039/C8OB01031E 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. Polish National Science Centre for grant OPUS (2011/01/B/ST5/03900). The study was carried out at the Biological and Chemical Research Centre, University of Warsaw, established within a project co-financed by the European Union through the European Regional Development Fund under the Operational Programme Innovative Economy 2007–2013. R. Q. thanks financial support provided by Consejería de Educación – Junta de Castilla y León (Project BU092U16) application/pdf eng Royal Society of Chemistry Organic & Biomolecular Chemistry. 2018, V. 16, n. 28, p. 5188-5196 https://doi.org/10.1039/C8OB01031E info:eu-repo/grantAgreement/JCyL/BU092U16 info:eu-repo/grantAgreement/PolishNational ScienceCentre/2011-01-B-ST5-03900 Química orgánica Chemistry, Organic 1,8-Diamidocarbazoles: an easily tuneable family of fluorescent anion sensors and transporters info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion info:eu-repo/semantics/openAccess THUMBNAIL Bąk-OBC_2018.pdf.jpg Bąk-OBC_2018.pdf.jpg IM Thumbnail image/jpeg 4891 https://riubu.ubu.es/bitstream/10259/4880/4/B%c4%85k-OBC_2018.pdf.jpg 2564ec6fa20b2acfb7641b46dec2a286 MD5 4 ORIGINAL Bąk-OBC_2018.pdf Bąk-OBC_2018.pdf application/pdf 837068 https://riubu.ubu.es/bitstream/10259/4880/1/B%c4%85k-OBC_2018.pdf 98466eb36999009f90d5567ab5ac2e55 MD5 1 LICENSE license.txt license.txt text/plain; charset=utf-8 999 https://riubu.ubu.es/bitstream/10259/4880/2/license.txt b295bcbce42e2caabeb0c623d3860c06 MD5 2 TEXT Bąk-OBC_2018.pdf.txt Bąk-OBC_2018.pdf.txt Extracted text text/plain 33618 https://riubu.ubu.es/bitstream/10259/4880/3/B%c4%85k-OBC_2018.pdf.txt 72c07ef6adb8638cfb4057cb1d6fc1f1 MD5 3 10259/4880 oai:riubu.ubu.es:10259/4880 2022-12-20 12:47:51.224 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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