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Fluorescein-N-Methylimidazole Conjugate as Cu2+ Sensor in Mixed Aqueous Media Through Electron Transfer

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Abstract

A new highly selective, chromogenic, and fluorogenic Cu2+ chemosensor, fluorescein-N-methylimidazole conjugate 1, and another fluorescein-N-imidazole conjugate 2 were synthesized and investigated by UV-visible and fluorescence spectroscopy. The sensing of Cu2+ quenches the emission band of 1 at λmax = 525 nm, with an association constant (K a = 1.0 x 107 M−1) and a stoichiometry of 1:1 in a buffered H2O: MeOH solution (4:1, pH = 7.4). The Cu2+ detection limit for chemosensor 1 is 37 nM. The presence of the N-methyl group in 1 increased the Cu2+ binding selectivity, resulting in a stronger binding constant and a broader pH working range (pH 5–10) in comparison to 2. The fluorescence in 1 and 2 is caused by electron transfer phenomenon from the imidazole nitrogen to fluorescein, which is readily inhibited by Cu2+ binding.

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Acknowledgments

The authors gratefully acknowledge the Center of Research Excellence in Nanotechnology (CENT) in King Fahd University of Petroleum and Minerals for providing funds and availing its facilities for analysis and Center of Research Excellence in Renewable Energy, King Fahd University of Petroleum and Minerals for providing us with the Spectrofluorometer for analysis.

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Authors and Affiliations

  1. Center of Research Excellence in Nanotechnology, King Fahd University of Petroleum and Minerals, Dhahran, 31261, Saudi Arabia

    Aasif Helal, Zain H. Yamani & M. Nasiruzzaman Shaikh

  2. Department of Applied Chemistry, Kyungpook National University, Daegu, 702-701, Republic of Korea

    Hong-Seok Kim

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  1. Aasif Helal
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  2. Hong-Seok Kim
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Correspondence to Aasif Helal.

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Helal, A., Kim, HS., Yamani, Z.H. et al. Fluorescein-N-Methylimidazole Conjugate as Cu2+ Sensor in Mixed Aqueous Media Through Electron Transfer. J Fluoresc 26, 1–9 (2016). https://doi.org/10.1007/s10895-015-1713-z

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