UV-Vis spectroscopic and colorimetric anion detection and fluorescence properties of new 3-amino-4-hydroxybenzenesulfonic acid-based Schiff bases depending on the strength and position of the electron donor substitution

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dc.authoridKARATAY, Ahmet/0000-0001-9373-801X
dc.authoridPepe, Yasemin/0000-0002-5384-2039
dc.contributor.authorYildiz, Elif Akhuseyin
dc.contributor.authorPepe, Yasemin
dc.contributor.authorErdener, Digdem
dc.contributor.authorKaratay, Ahmet
dc.contributor.authorBoyacioglu, Bahadir
dc.contributor.authorUnver, Hueseyin
dc.contributor.authorYapar, Gonul
dc.date.accessioned2025-01-27T20:26:51Z
dc.date.available2025-01-27T20:26:51Z
dc.date.issued2023
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractIn this study, 3-amino-4-hydroxybenzenesulfonic acid-based imine compounds; 3-(2,5-dihydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (1), 3-(2,4-dihydroxybenzylideneamino)-4-hydroxybenzenesulfonic acid (2) and 4-hydroxy-3-(2-hydroxy-3-methoxybenzylideneamino)-4-hydroxybenzenesulfonic acid (3) was synthesized. The compounds were analyzed using various spectroscopy methods, and the experimental UV-vis data matched the theoretical predictions. The compound 1 displayed lower stability, higher reactivity, and easier photoexcitation due to a smaller HOMO-LUMO energy gap. The investigated compounds 1-3 showed promise as chemosensors for anions, providing visible detection in daylight conditions. The compound 3 exhibited selective fluorescence at specific wavelengths. The compounds 1-3 interacted with DNA through electrostatic interactions. Also, compounds 1-3 showed higher antioxidant activity than BHT. However, fluorescence measurements indicated that the emission signals were strongly influenced by the position and strength of the electron-donating group. Adding a hydroxy or methoxy moiety near the -OH group on the phenyl ring decreased the fluorescence signal due to intersystem crossing and intramolecular charge transfer mechanisms, respectively. These findings were supported by femtosecond transient absorption spectroscopy measurements. The results emphasize the significance of substituents in imines derived from 3-amino-4-hydroxybenzenesulfonic acid in determining their biological activities, as well as their optical and sensor properties.
dc.identifier.doi10.1088/1402-4896/ace806
dc.identifier.issn0031-8949
dc.identifier.issn1402-4896
dc.identifier.issue8
dc.identifier.scopus2-s2.0-85166901510
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1088/1402-4896/ace806
dc.identifier.urihttps://hdl.handle.net/20.500.12428/22459
dc.identifier.volume98
dc.identifier.wosWOS:001040021500001
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherIop Publishing Ltd
dc.relation.ispartofPhysica Scripta
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WoS_20250125
dc.subjectbiological activity
dc.subject3-amino-4-hydroxybenzenesulfonic acid
dc.subjectfemtosecond transient absorption spectroscopy
dc.subjectanion sensor
dc.subjectDPPH method
dc.subjectdensity functional theory (DFT)
dc.titleUV-Vis spectroscopic and colorimetric anion detection and fluorescence properties of new 3-amino-4-hydroxybenzenesulfonic acid-based Schiff bases depending on the strength and position of the electron donor substitution
dc.typeArticle

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