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Colorimetric ‘naked eye’ sensor for fluoride ion based on isatin hydrazones via hydrogen bond formation: Design, Synthesis and Characterization ascertained by Nuclear Magnetic resonance, Ultravoilet-Visible, Computational and Electrochemical studies

Highlights•A new colorimetric sensor R-IND was designed and synthesized.•The sensor R-IND displayed high selectivity and sensitivity towards fluoride ion in both 100% ACN and 20% aqua ACN medium.•The binding constant and stoichiometry of the sensor-anion complex were calculated.•The sensor was also been utilized for the electrochemical sensing of fluoride ions.AbstractA new colorimetric sensor ‘R-IND’ based on isatin hydrazones have been designed and synthesized by simple Schiff base reaction. The anion sensing properties of R-IND were examined, characterized by common spectroscopic techniques such as Fourier Transform-Infrared (FT-IR), Ultraviolet-Visible (UV–Visible), Proton and Carbon Nuclear Magnetic Resonance (1H & 13C NMR), Electrospray Ionization Mass Spectroscopy (ESI-MS) and electrochemical studies. The sensor R-IND bearing ortho hydroxy group and amine group acting as binding sites. The sensor R-IND exhibited sensitive and selective sensing towards F- ion over the other competitive anions like Cl-, I-, Br-, H2PO4-, AcO-, CN-, NO3-, ClO4- and HSO4- in 100% Aetonitrile and 20% aqua Acetonitrile medium. The bathochromic shift of 222 nm and 228 nm was observed in UV-Vis spectra with a color change from pale yellow to purple which is due to the complex formation between R-IND and F- ion through hydrogen bond formation. This was further accounted by 1H NMR titration. The Job’s plot reveals 1:2 stoichiometry between the host-guest complex. Binding and association constants were found to be 1.72×109 M-1, 2.82×109 M-1 and 6.0×105 M-1, 2.0×106 M-1 in 100% ACN and 20% aqua ACN respectively. The detection limit of sensor R-IND was turned out to be 0.45 and 0.41 ppm for F- ion in organic and aqua organic medium which is lesser than World Health Organization (WHO) permission level (1 ppm). The characteristic potential difference of 1.069 V has been observed for R-IND+F- complex in the electrochemical study. Finally, economically viable paper-based colorimetric test strips of R-IND were developed to detect the F- ions in 100% aqueous solution.

سنسور "چشم غیر مسلح" کلریتی برای یون فلوراید براساس هیدرات‌های ایزوآتین از طریق تشکیل پیوند هیدروژنی: طراحی، سنتز و تعیین ویژگی توسط رزونانس مغناطیسی هسته‌ای، مطالعات آلتراویل - مرئی، محاسباتی و الکتروشیمیایی

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