Pyrazoline-Based Fluorescent Probe: Synthesis, Characterization, Theoretical Simulation, and Detection of Picric Acid

Promila Sharma; Mohamad Yusuf; Ashok Kumar Malik

doi:10.1007/s10895-023-03414-w

Pyrazoline-Based Fluorescent Probe: Synthesis, Characterization, Theoretical Simulation, and Detection of Picric Acid

J Fluoresc. 2023 Aug 30. doi: 10.1007/s10895-023-03414-w. Online ahead of print.

Authors

Promila Sharma^{1

2}, Mohamad Yusuf¹, Ashok Kumar Malik³

Affiliations

¹ Department of Chemistry, Punjabi University, Patiala, 147002, India.
² Department of Chemistry, RIMT University, Mandigobindgargh, 147301, India.
³ Department of Chemistry, Punjabi University, Patiala, 147002, India. malik_chem2002@yahoo.co.uk.

PMID: 37646875
DOI: 10.1007/s10895-023-03414-w

Abstract

2-Pyrazoline containing benzothiazole ring 2-[1-(1,3-benzothiazol-2-yl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]phenol (BP) have been synthesized for the effective identification of picric acid over other competing nitro compounds using fluorescence technique. The pyrazoline BP showed quenching efficiency as high as 82% comparative to other nitro aromatics. The limit of detection and limit of quantification were found to be 1.1 μM and 3.3 μM. The possible mechanism with the quenched PA detection efficiency was based on fluorescence energy transfer and photoinduced electron transfer. Moreover, the observed results were supported by the optimized structures of the compounds using the DFT/B3LYP/6-311G/LanL2DZ method. Eventually, the pyrazoline derivative BP was further utilized for natural water samples, showing recoveries in the 87.62-101.09% and RSD was less than 3%.

Keywords: Benzothiazole; Density functional theory; Fluorescence quenching; Picric acid; Pyrazoline.