Abstract
Phenyl-4,4-di(3,6-dibutoxyphthalonitrile) ( 3 ) was synthesized by the reaction of 1,4-phenylenebisboronic acid ( 1 ) and 4-bromo-3,6-dibutoxyphthalonitrile ( 2 ), using Suzuki cross-coupling reaction. The newly synthesized compound ( 3 ) was characterized by FT-IR, MALDI-MS, ESI-MS, 1 H-NMR, 13 C-NMR, and 13 C-DEPT-135-NMR. The fluorescence property of phenyl-4,4-di(3,6-dibutoxyphthalonitrile) ( 3 ) towards various metal ions was investigated by fluorescence spectroscopy, and it was observed thatthe compound ( 3 ) displayed a significantly ‘turn-off’ response to Fe 3+ , which was referred to 1:2 complex formation between ligand ( 3 ) and Fe 3+ . The compound was also studied via density functional theory calculations revealing the interaction mechanism of the molecule with Fe 3+ ions.
Highlights
Among the most abundant and versatile transition metal ions, iron is of vital importance to living systems because of its significant role in biochemical processes, such as oxidoreductase catalysis, oxygen transport, and electron transport [1,2,3]
Atomic absorption spectrometry (AAS), flow-injection chemiluminescence, spectrophotometry, inductively coupled plasma-optical emission spectrometry/ mass spectrometry (ICP-OES/MS), fluorimetry, and cathodic stripping voltammetry are used for the determination of the Fe3+ and Fe2+ ions, but these methods suffer from restrictions like using multifaceted instruments and interference with other metals [7,8]
Based on the abovementioned benefits, this study focuses on the synthesis of the new fluorescence chemosensor phthalonitrile derivative (3) for the determination of the Fe3+ ions
Summary
Among the most abundant and versatile transition metal ions, iron is of vital importance to living systems because of its significant role in biochemical processes, such as oxidoreductase catalysis, oxygen transport, and electron transport [1,2,3]. Phenyl-4,4-di(3,6-dibutoxyphthalonitrile) (3) was synthesized and characterized by spectroscopic methods, including FT-IR, MALDI-MS, ESI-MS, 1H-NMR, 13C-NMR, and 13C-DEPT-135-NMR. Chemosensor behavior of this phthalonitrile compound (3) was determined towards different metal ions (Ag+, Al3+, Ba2+, Ca2+, Cd2+, Co2+, Cr3+, Cs+, Cu2+, Fe2+, Fe3+, Hg2+, K+, Li+, Mg2+, Mn2+, Na+, Ni2+, Pb2+, Zn2+) by using fluorescence spectroscopy in solution. All these various cations were tested, and it was demonstrated that a turn-off chemosensor response was achieved towards Fe3+ selectively.
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