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Synthesis, Crystal Structure and Fluorimetric Study of 2-phenylphthalazin-1(2H)-one: a Highly Selective Florescent Chemosensor for Detection of Fe3+ and Fe2+ Metal Ions

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Abstract

A ligand, 2-phenylphthalazin-1(2H)-one (K), was synthesized by refluxing 2-formylbenzoic acid with phenyl hydrazine in presence of ethanol. FTIR, elemental analysis and single crystal XRD techniques were used to elucidate the structure. Fluorimetric turn-off response was recorded when solution of ligand (K) in DMF was treated with aqueous solution of Fe3+ and Fe2+ metal ions. No specific changes were observed on addition of other metal ions (Pb2+, Cd2+, Mn2+, Zn2+, Ba2+, Ni2+, Al3+, Ag1+, Co2+, Ca2+, Cu2+, Mg2+, Cr3+). Limit of Detection (LOD) was calculated for Fe2 and Fe3+as 2.4 µM and 2.5µM respectively, which is quite below to the recommended value 5.4 µM of the Environment Protection Agency of USA. Association constants for Fe3+ and Fe2+ metal ions were determined as 6 × 10–4 M−1 and 3.6 × 10–4 M−1 respectively. Benesi-Hildebrand plot confirmed 1:1 binding ratio between metal ions and ligand.

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Abbreviations

(K):

2-phenylphthalazin-1(2H)-one

(AAS):

flame atomic absorption spectroscopy

HPLC:

Inductively coupled plasma mass spectroscopy, atomic absorption spectroscopy, electrothermal atomization atomic absorption spectrometry

ETAAS:

electrothermal atomization atomic absorption spectrometry

FRET:

fluorescence resonance energy transfer

ICT:

intra- ligand charge transfer

PET:

photo-induced electron transfer

PET:

excited state intramolecular proton transfer

LOD:

Limit of Detection

LOQ:

and Limit of Quantification

EPAUS:

Environment Protection Agency of United States of America

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Acknowledgements

We gratefully acknowledge financial assistance from the Higher Education Commission of Pakistan, HEC-NRPU project no.20-17612/NRPU/R&D/HEC/2021 and GCU-ORIC Project no. No. 85/ORIC/23.

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There was no funding to disclose.

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Authors and Affiliations

  1. Materials Chemistry Laboratory, Department of Chemistry, Govt. College University, Lahore, 54000, Pakistan

    Shahzad Sharif, Muhammad Shahbaz, Muhammad Aqib Khurshid, Maryam Musaffa Anbar & Birra Dar

  2. Department of Occupat Health & Safety, Faculty of Health Sciences, Sinop University, TR-57000, Sinop, Turkey

    Onur Şahin

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  1. Shahzad Sharif
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  2. Muhammad Shahbaz
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Contributions

Shahzad Sharif: Conceptualization, Supervision, Project administration, review, editing. Muhammad Shahbaz: Design experimentation, writing original draft. Onur Şahin: Single XRD analysis, write up, Muhammad Aqib Khurshid: Methodology and write up. Maryam Musaffa Anbar: Experimental set up, sample preparation. Birra Dar: Luminescence experimentation.

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Sharif, S., Shahbaz, M., Şahin, O. et al. Synthesis, Crystal Structure and Fluorimetric Study of 2-phenylphthalazin-1(2H)-one: a Highly Selective Florescent Chemosensor for Detection of Fe3+ and Fe2+ Metal Ions. J Fluoresc (2023). https://doi.org/10.1007/s10895-023-03484-w

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