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A Fluorescent Hypochlorite Probe Built on 1,10-Phenanthroline Scaffold and its Ion Recognition Features

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Abstract

In this study, the synthesis of 7-((Hydroxyimino)methyl)-1,10-phenanthroline-4-carbaldehyde oxime (1) in two steps starting from 4,7-dimethyl-1,10-phenanthroline (2) is reported. It is found that compound 1 can be used as a fluorogenic probe for the detection of hypochlorite ion in aqueous solution. NMR and mass spectral analysis indicate that probe 1 undergoes a chemical transformation through its oxime units upon treatment with hypochlorite, which results in a remarkable enhancement of the emission intensity. Also, metal ion recognition properties of probe 1 is investigated. It is noted that compound 1 is responsive to Zn2+, Cd2+, Ni2+ and Cu2+ metal ions, which reduced the emission intensity under identical conditions.

The design, synthesis and properties of a new fluorescent hypochlorite probe is described. It is found that probe 1 immediately undergoes an oxidation reaction with NaClO through its oxime units in 0.1 M Na2CO3-NaHCO3 buffer containing DMF (pH = 9.0, 30:1 v/v) at room temperature, which resulted in a remarkable enhancement of the emission intensity. It is noteworthy that this novel probe 1 is highly selective to hypochlorite ion when compared to some other ROS and anions. On the other hand, probe 1 also induces turn-off fluorogenic responses to metal ions such as Zn2+, Cd2+, Ni2+ and Cu2+ ions under identical conditions.

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Acknowledgments

The author is indebted to Aksaray University for partial financial support of this work (ASU BAP 2015-092).

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  1. Health Services Vocational School & ASUBTAM BioNanoTech Lab., Aksaray University, TR-68100, Aksaray, Turkey

    Melek Pamuk Algi

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Correspondence to Melek Pamuk Algi.

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Algi, M.P. A Fluorescent Hypochlorite Probe Built on 1,10-Phenanthroline Scaffold and its Ion Recognition Features. J Fluoresc 26, 487–496 (2016). https://doi.org/10.1007/s10895-015-1734-7

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