Highly selective and sensitive fluorescent “TURN-ON” furan-based Schiff base for zinc(ii) ion probing: chemical synthesis, DFT studies, and X-ray crystal structure

N. R., Divyashree and Revanasiddappa, H. D. and Yathirajan, H. S. and Bhavya, N. R. and Mahendra, M. and Iqbal, Muzaffar and Shivamallu, Chandan and Amachawadi, Raghavendra G. and Shiva Prasad, K. (2023) Highly selective and sensitive fluorescent “TURN-ON” furan-based Schiff base for zinc(ii) ion probing: chemical synthesis, DFT studies, and X-ray crystal structure. New Journal of Chemistry, 47. pp. 17420-17433. ISSN 1369-9261

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Abstract

A simple and efficient fluorescent probe (E)-4-bromo-2-((((5-methylfuran-2-yl)methyl)imino)methyl)phenol (BFMP) for the detection of Zn2+ ions was synthesized by the condensation of 5-methyl-furfurylamine and 5-bromosalicylaldehyde. Elemental analysis, LC-MS, ATR-IR spectroscopy, and NMR (1H and 13C) spectroscopy were performed to confirm the structures of the Schiff base ligand and its Zn(II) complex. Further, the molecular structure of BFMP was confirmed by single-crystal XRD. It is noteworthy that BFMP displayed favourable behaviour of the florescent active molecule. The BFMP solution was yellow, which after the addition of the Zn2+ solution became colourless, as observed by the naked eye. Moreover, under ultraviolet (UV) radiation, a maximum absorption at 425 nm and a large fluorescence enhancement at 560 nm were observed. BFMP was very selective to Zn2+ ions, even in the presence of other metal ions. This includes Cd2+, which has a binding constant (Ka) of 1.74 × 106 M−1, and a detection limit of this finding suggested that a fluorescence probe (BFMP) can be used to detect Zn2+ by colorimetric detection. The detection limit can reach up to 0.249 × 106 M−1. Furthermore, the efficiency of the ligand was tested using real water samples (lake and tap water), and the results revealed that BFMP acted more efficiently in both the tested water samples. The geometries of BFMP and BFMP–Zn2+ were investigated by the density functional theory (DFT) method using the B3LYP method with 6-311++G(d,p) and LAN2LZ basis sets, respectively. The optimized geometrical parameters obtained by the DFT calculation are in good agreement with the X-ray crystal structure data.

Item Type:	Article
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Chemistry
Depositing User:	C Swapna Library Assistant
Date Deposited:	29 Sep 2023 05:53
Last Modified:	29 Sep 2023 05:53
URI:	http://eprints.uni-mysore.ac.in/id/eprint/17747

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