Colorimetric probing and fluorescent chemosensor features of functionalized sulphonamide-azomethine derivatives

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dc.authoridKARATAY, Ahmet/0000-0001-9373-801X
dc.contributor.authorYildiz, Elif Akhuseyin
dc.contributor.authorErdener, Digdem
dc.contributor.authorTekin, Sezen
dc.contributor.authorKaratay, Ahmet
dc.contributor.authorBoyacioglu, Bahadir
dc.contributor.authorUnver, Huseyin
dc.contributor.authorYıldız, Mustafa
dc.date.accessioned2025-01-27T20:56:21Z
dc.date.available2025-01-27T20:56:21Z
dc.date.issued2022
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractIn this work, we have experimentally synthesized bromosulfonamide-based azomethine compounds through the reaction of 4-bromobenzenesulfonamide with 2-hydroxy-5-iodobenzaldehyde, 2-hydroxy-5-nitrobenzaldehyde, and 2-hydroxy-l-naphthaldehyde. We have also characterized the molecular structure of the investigated compounds with MS, H-1 NMR, FTIR and UV-vis spectra. Theoretically, using DFT and TD-DFT methods, we computed frontier molecular orbitals (FMOs) energies and UV-vis spectra as well. We have also obtained the electron localization function (ELF) maps to identify electrophilic substitution sites in the molecules and density of states (DOS) diagrams to show the composition of the fragment orbitals that contribute to the molecular orbitals. We have investigated steady-state absorption, emission features, and excited state dynamics to better understand the photophysical process of bromosulfonamide-based azomethines. It has been demonstrated that by adding a naphthalene unit, the absorption properties of azomethine into two branches. Besides, azomethine, including heavy iodo atoms, presents a slight decrement in the fluorescence intensity. According to thorough calculations of charge transfer dynamics using femtosecond transient absorption spectra, the bromosulfonamidebased azomethines with iodo atoms and incorporating naphthalene units exhibit an intersystem crossing mechanism following photoexcitation. The colorimetric response of the compounds in DMSO to the addition of the equivalent amount of anions (F- , Br- , I-, CN-, SCN-, ClO4-, HSO4-, AcO-, H2PO4- , N-3(-) and OH-) was investigated. In this regard, while the addition of F- ,CN- ,AcO- , H2PO4- and OH(- )anions into the solution containing the compounds resulted in a significant color change, the addition of Br-, I-, SCN-, ClO4- HSO4- and N-3 anions resulted in no color change.
dc.identifier.doi10.1016/j.jphotochem.2022.114188
dc.identifier.issn1010-6030
dc.identifier.issn1873-2666
dc.identifier.scopus2-s2.0-85135689646
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.jphotochem.2022.114188
dc.identifier.urihttps://hdl.handle.net/20.500.12428/26380
dc.identifier.volume433
dc.identifier.wosWOS:000882992100002
dc.identifier.wosqualityQ2
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakScopus
dc.language.isoen
dc.publisherElsevier Science Sa
dc.relation.ispartofJournal of Photochemistry and Photobiology A-Chemistry
dc.relation.publicationcategoryinfo:eu-repo/semantics/openAccess
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WoS_20250125
dc.subjectFunctionalized sulphonamide-azomethine derivatives
dc.subjectFemtosecond transient absorption spectroscopy
dc.subjectFluorescent sensors
dc.subjectColorimetric
dc.subjectDFT
dc.titleColorimetric probing and fluorescent chemosensor features of functionalized sulphonamide-azomethine derivatives
dc.typeArticle

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