Synthesis and investigation of bis(phenyl)fluorene and carbazole appended dipodal Schiff base for fluorescence sensing towards Sn(II) ion and its regioselective polymerization

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dc.authoridKaya, İsmet / 0000-0002-9813-2962
dc.authoridKolcu, Feyza / 0000-0002-2004-8859
dc.contributor.authorKolcu, Feyza
dc.contributor.authorÇulhaoğlu, Süleyman
dc.contributor.authorKaya, İsmet
dc.date.accessioned2025-01-27T20:31:45Z
dc.date.available2025-01-27T20:31:45Z
dc.date.issued2023
dc.departmentÇanakkale Onsekiz Mart Üniversitesi
dc.description.abstractOne-pot condensation reaction between 9,9-Bis(4-aminophenyl)fluorene and 9-Ethyl-9H-carbazole-3-carbalde-hyde afforded a chemosensor ((N,N ')-4,4 '-(9H-fluorene-9,9-diyl)bis(N-((9-ethyl-9H-carbazol-2-yl)methylene) aniline, SB) having Schiff base skeleton. The further step was the synthesis of the polymer (P-SB) via oxidative polycondesation reaction of SB. FT-IR, H-1 NMR and C-13 NMR instruments were used to characterize the func-tional groups on the monomer and polymer. Thermal stability and electrochemical features of SB and P-SB were characterized by thermogravimetric analysis-differential thermal analyses (TG-DTA) and cyclic voltammetry (CV), respectively. The glass transition and surface image of P-SB were determined from DSC and SEM mea-surements, respectively. UV-vis and photoluminescence spectroscopy (PL) allowed to determine the optical properties of SB and P-SB. The obtained polymer, which had the weight average molecular weight of 8400 Da identified by gel permeation chromatography (GPC), exhibited fluorescence property. The synthesized turn-on fluorogenic chemosensor SB showed high selectivity and sensitivity towards Sn2+ among the cations of Ag+, K+, Hg2+, Mn2+, Cd2+, Sn2+, Ca2+, Pb2+, Zn2+, Co2+, Ni2+, Cu2+, Fe3+, Al3+, Cr3+ and Cr6+. The fluorescence turn-on recognition process for the detection of Sn2+ was related to the restriction of C=N isomerization, fol-lowed by inhibiting intramolecular charge transfer (ICT), with consequent chelation-enhanced fluorescence (CHEF) mechanism. The stoichiometry ratio of the analyte-sensor adduct in the solution was found to be 1:1 by Job's plot method concomitant with a dramatic increase in fluorescent signal at 471 nm and a marked color change from colorless to turquoise blue upon addition of Sn2+ ions. Limit of detection value for the formation of SB-Sn2+ chelation was calculated as 3.37 nM. No change in PL intensity of SB-Sn2+ chelation was observed in the company of other metal ions. Reversibility of the chemosensor in its binding towards Sn2+ was demonstrated in the presence of chelating agent EDTA. The synthesized SB could effectively detect Sn2+ ion as a fluorescent sensor.
dc.description.sponsorshipCanakkale Onsekiz Mart University scientific research project commission [FBA-2021-3552]
dc.description.sponsorshipThe authors thank Canakkale Onsekiz Mart University scientific research project commission for support with the project number (Project Nu.: FBA-2021-3552).
dc.identifier.doi10.1016/j.jphotochem.2023.114665
dc.identifier.issn1010-6030
dc.identifier.issn1873-2666
dc.identifier.scopus2-s2.0-85150755761
dc.identifier.scopusqualityQ1
dc.identifier.urihttps://doi.org/10.1016/j.jphotochem.2023.114665
dc.identifier.urihttps://hdl.handle.net/20.500.12428/23260
dc.identifier.volume441
dc.identifier.wosWOS:001056670700001
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.subjectSchiff base
dc.subjectOxidative polycondensation
dc.subjectFluorescent chemosensor
dc.subjectCHEF
dc.subjectSn2+
dc.subjectBenesi-Hildebrand
dc.titleSynthesis and investigation of bis(phenyl)fluorene and carbazole appended dipodal Schiff base for fluorescence sensing towards Sn(II) ion and its regioselective polymerization
dc.typeArticle

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