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Bis-Benzimidazolyl Diamide Based Fluorescent Probe for Copper(II): Synthesis, Structural and Fluorescence Studies

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Abstract

A new fluorescent probe based on a bis-benzimidazole diamide N 2,N 2′-bis[(1-ethyl-benzimidazol-2-yl)methyl]biphenyl-2,2′-dicarboxamide ligand L 1 with a biphenyl spacer group and a Copper(II) trinuclear metallacycle has been synthesized and characterized by X-ray single crystallography, elemental and spectral (FT-IR, 1H & 13C NMR, UV-Visible) analysis. The fluorescence spectra of L 1 in MeOH show an emission band centered at 300 nm. This band arises due to benzimidazolyl moiety in the ligating system. The diamide L 1 in the presence of Cu2+ show the simultaneous ‘quenching’ of (300 nm) and ‘enhancement’ of (375 nm) emission band. Similar fluorescence behavior was found in water–methanol mixture (9:1). The new emission band at 375 nm is attributed to intra ligand π–π* transition of the biphenyl moiety. L 1 exhibited high selectivity and sensitivity towards Cu2+ in both the medium over other common metal ions like Ni2+, Co2+, Mn2+, Mg2+, Zn2+, Pb2+ and Hg2+. The binding constant with Cu2+ was calculated by the Benesi-Hildebrand equation. Selective “off-on-off” behavior of L 1 in methanol has also been studied. The fluorescent intensity of 375 nm bands in L 1 enhances (turns-on) upon addition of Cu2+ and quenches (turn-off) upon addition of Na2-EDTA.

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Acknowledgments

The authors are grateful to University of Delhi, Delhi for a special grant. We are thankful to USIC-CIF, University of Delhi, Delhi, India for NMR and Single Crystal X-ray data. One of the authors is thankful to UGC for providing senior research fellowship (SRF).

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  1. Department of Chemistry, University of Delhi, Delhi, 110007, India

    Kuldeep Mahiya & Pavan Mathur

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  1. Kuldeep Mahiya
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  2. Pavan Mathur
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Correspondence to Pavan Mathur.

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Mahiya, K., Mathur, P. Bis-Benzimidazolyl Diamide Based Fluorescent Probe for Copper(II): Synthesis, Structural and Fluorescence Studies. J Fluoresc 23, 767–776 (2013). https://doi.org/10.1007/s10895-013-1182-1

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