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Turn‐on fluorescent probe for Zn 2+ ions based on thiazolidine derivative
Author(s) -
Genç Bilgiçli Hayriye,
Bilgiçli Ahmet T.,
Günsel Armağan,
Tüzün Burak,
Ergön Derya,
Yarasir M. Nilüfer,
Zengin Mustafa
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5624
Subject(s) - chemistry , bathochromic shift , metal ions in aqueous solution , thiazolidine , fluorescence , ion , detection limit , homo/lumo , molecule , analytical chemistry (journal) , molecular orbital , inorganic chemistry , nuclear chemistry , stereochemistry , organic chemistry , physics , chromatography , quantum mechanics
In this study, simple on–off fluorescent/UV–visible (UV–Vis) probes were easily prepared using 2‐(2‐hydroxyphenyl)thiazolidine‐4‐carboxylic acid ( Sen‐1 ) and/or 2‐(2‐hydroxy‐5‐nitrophenyl)thiazolidine‐4‐carboxylic acid ( Sen‐2 ) for fast detection of Zn 2+ ions. Their sensing properties towards common metal ions were investigated using UV–Vis and fluorescence spectroscopies. Sen‐1 and Sen‐2 displayed a significant change with the addition of Zn 2+ ions in the UV–Vis spectra. The addition of Zn 2+ ions induced a 104 nm bathochromic shift for Sen‐1 . The binding ratio towards Zn 2+ metal ions was determined to be 1:1 by using Job plot analysis and fluorescence spectroscopy. The association constant and free energy (Δ G ) of Sen‐1 and Sen‐2 towards Zn 2+ ions were calculated by the Benesi–Hildebrand equation. The limit of detection of Sen‐1 towards Zn 2+ ions is 3.73 × 10 −8 M, which is about 1/100 of the value recommended by the World Health Organization for drinking water. Sen‐1 was successfully applied to detect Zn 2+ ions in water samples and the fluorescence test strip was prepared for visual detection of Zn 2+ ions. Finally, the quantum chemical parameters of Sen‐1 and Sen‐2 , such as highest occupied molecular orbital, lowest unoccupied molecular orbital, and chemical hardness, were investigated by the Becke, three‐parameter, Lee–Yang–Parr, Hartree–Fock, and M062x methods.