Fluorescence Sensors Based on Hydroxycarbazole for the Determination of Neurodegeneration-Related Halide Anions

Simple item page
dc.contributor.authorGonzález Ruiz, Víctor
dc.contributor.authorCores, Ángel
dc.contributor.authorCaja, M. Mar
dc.contributor.authorSridharan, Vellaisamy
dc.contributor.authorVillacampa, Mercedes
dc.contributor.authorMartín, M. Antonia
dc.contributor.authorOlives Barba, Ana Isabel
dc.contributor.authorMenéndez Ramos, José Carlos
dc.date.accessioned2023-06-22T11:04:09Z
dc.date.available2023-06-22T11:04:09Z
dc.date.issued2022-03-14
dc.description.abstractThe environmental presence of anions of natural origin or anthropogenic origin is gradually increasing. As a tool to tackle this problem, carbazole derivatives are an attractive gateway to the development of luminescent chemosensors. Considering the different mechanisms proposed for anion recognition, the fluorescence properties and anion-binding response of several newly synthesised carbazole derivatives were studied. Potential anion sensors were designed so that they combined the native fluorescence of carbazole with the presence of hydrogen bonding donor groups in critical positions for anion recognition. These compounds were synthesised by a feasible and non-expensive procedure using palladium-promoted cyclodehydrogenation of suitable diarylamine under microwave irradiation. In comparison to the other carbazole derivatives studied, 1-hydroxycarbazole proved to be useful as a fluorescent sensor for anions, as it was able to sensitively recognise fluoride and chloride anions by establishing hydrogen bond interactions through the hydrogen atoms on the pyrrolic nitrogen and the hydroxy group. Solvent effects and excited-state proton transfer (ESPT) of the carbazole derivatives are described to discard the role of the anions as Brönsted bases on the observed fluorescence behaviour of the sensors. The anion–sensor interaction was confirmed by 1H-NMR. Molecular modelling was employed to propose a mode of recognition of the sensor in terms of complex stability and interatomic distances. 1-hydroxycarbazole was employed for the quantitation of fluoride and chloride anions in commercially available medicinal spring water and mouthwash samples.
dc.description.departmentDepto. de Química Analítica
dc.description.departmentDepto. de Química en Ciencias Farmacéuticas
dc.description.facultyFac. de Ciencias Químicas
dc.description.facultyFac. de Farmacia
dc.description.refereedTRUE
dc.description.sponsorshipMinisterio de Ciencia e Innovación (MICINN)
dc.description.sponsorshipComunidad de Madrid
dc.description.statuspub
dc.eprint.idhttps://eprints.ucm.es/id/eprint/74829
dc.identifier.doi10.3390/bios12030175
dc.identifier.issn2079-6374
dc.identifier.officialurlhttps://doi.org/10.3390/bios12030175
dc.identifier.relatedurlhttps://www.mdpi.com/2079-6374/12/3/175
dc.identifier.urihttps://hdl.handle.net/20.500.14352/72069
dc.issue.number3
dc.journal.titleBiosensors
dc.language.isoeng
dc.page.initial175
dc.publisherMPDI
dc.relation.projectIDRTI2018-097662-B-I00
dc.relation.projectIDB2017/BMD-3813
dc.rightsAtribución 3.0 España
dc.rights.accessRightsopen access
dc.rights.urihttps://creativecommons.org/licenses/by/3.0/es/
dc.subject.keywordfluorescent sensors
dc.subject.keywordhydrogen bonds
dc.subject.keywordcarbazole derivatives
dc.subject.keywordmicrowave-assisted synthesis
dc.subject.keywordhalide toxicity
dc.subject.keywordhalide quantitation
dc.subject.ucmQuímica analítica (Química)
dc.subject.ucmFarmacia
dc.subject.unesco2301 Química Analítica
dc.titleFluorescence Sensors Based on Hydroxycarbazole for the Determination of Neurodegeneration-Related Halide Anions
dc.typejournal article
dc.volume.number12
dspace.entity.typePublication
relation.isAuthorOfPublication109c167c-4d5d-41f6-be94-4ca6160136a5
relation.isAuthorOfPublication4c8ca147-677d-4846-97b7-d4419662ff60
relation.isAuthorOfPublication.latestForDiscovery109c167c-4d5d-41f6-be94-4ca6160136a5
Download
Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
biosensors-12-00175-v2.pdf
Size:
2.85 MB
Format:
Adobe Portable Document Format
downoload Download
Collections
Artículos