Novel quinoxaline based chemosensors with selective dual mode of action: nucleophilic addition and host–guest type complex formation

dc.bibliographicCitation.firstPage64009eng
dc.bibliographicCitation.issue68eng
dc.bibliographicCitation.journalTitleRSC Advances : an international journal to further the chemical scienceseng
dc.bibliographicCitation.lastPage64018eng
dc.bibliographicCitation.volume6eng
dc.contributor.authorIshtiaq, Marium
dc.contributor.authorMunir, Iqra
dc.contributor.authoral-Rashida, Mariya
dc.contributor.authorMaria, Maria
dc.contributor.authorAyub, Khurshid
dc.contributor.authorIqbal, Jamshed
dc.contributor.authorLudwig, Ralf
dc.contributor.authorKhan, Khalid Mohammed
dc.contributor.authorAli, Syed Abid
dc.contributor.authorHameed, Abdul
dc.date.accessioned2022-05-10T07:02:46Z
dc.date.available2022-05-10T07:02:46Z
dc.date.issued2016
dc.description.abstractNew quinoxalinium salts 1–5 have been exploited as chemosensors via naked eye, UV-Vis absorption, fluorescence quenching and 1H NMR experiments. New sensors 1–5 showed a dual mode, nucleophilic addition and a host–guest type complex towards anion (F−, AcO− and ascorbate) detection. Small anions (F−/AcO−) showed nucleophilic addition at the C2 position of the quinoxalinium cation, while larger anions (ascorbate), revealed the formation of a host–guest type complex due to the steric hindrance posed by the C3 of the phenyl ring. Nucleophilic addition of small anions (F−/AcO−) leads to the de-aromatization of the quinoxalinium cation. However in the case of the larger anion, ascorbate, the host–guest type complex formation induces changes in the absorption/fluorescence signals of the quinoxalinium moiety. This selective binding has been confirmed on the basis of the 1H NMR spectroscopic technique, whereupon nucleophilic addition of small anions (F−/AcO−) was confirmed by monitoring the characteristic proton NMR signals of Ha and the methylene protons (CH2), which were clearly shifted in the cases of fluoride and acetate ion addition confirming the de-aromatization and nucleophilic addition. Whereas no such peak shifting was observed in the case of ascorbate ion addition confirming the non-covalent addition of ascorbate. Theoretical insight into the selectivity and complexation behavior of the ascorbate ion with the quinoxaline moiety is gained through density functional theory (DFT) calculations. Moreover, the absorption properties of these complexes are modeled theoretically, and compared with the experimental data. In addition, the thermal decomposition of sensors (1 and 2) has been studied by the means of differential scanning calorimetry (DSC), thermogravimetry (TG), and differential thermogravimetry (DTG) to signify their utility at variable temperatures.eng
dc.description.versionpublishedVersioneng
dc.identifier.urihttps://oa.tib.eu/renate/handle/123456789/8907
dc.identifier.urihttps://doi.org/10.34657/7945
dc.language.isoengeng
dc.relation.doihttps://doi.org/10.1039/c6ra14134j
dc.relation.essn2046-2069
dc.rights.licenseCC BY-NC 3.0 Unportedeng
dc.rights.urihttps://creativecommons.org/licenses/by-nc/3.0/eng
dc.subject.ddc540eng
dc.subject.otherAddition reactionseng
dc.subject.otherComplexationeng
dc.subject.otherDecompositioneng
dc.subject.otherDensity functional theoryeng
dc.subject.otherDifferential scanning calorimetryeng
dc.subject.otherNegative ionseng
dc.subject.otherNuclear magnetic resonance spectroscopyeng
dc.subject.otherPhysiologyeng
dc.subject.otherPositive ionseng
dc.subject.otherQuenchingeng
dc.subject.otherThermogravimetric analysiseng
dc.subject.otherAbsorption propertyeng
dc.subject.otherComplex formationseng
dc.subject.otherDifferential thermogravimetryeng
dc.subject.otherFluorescence quenchingeng
dc.subject.otherNucleophilic additionseng
dc.subject.otherSpectroscopic techniqueeng
dc.subject.otherUV-vis absorptionseng
dc.subject.otherVariable temperatureeng
dc.subject.otherIonseng
dc.titleNovel quinoxaline based chemosensors with selective dual mode of action: nucleophilic addition and host–guest type complex formationeng
dc.typeArticleeng
dc.typeTexteng
tib.accessRightsopenAccesseng
wgl.contributorLIKATeng
wgl.subjectChemieeng
wgl.typeZeitschriftenartikeleng
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