title: A Fluorescent Hypochlorite Probe Built on 1,10-Phenanthroline Scaffold and its Ion Recognition Features.
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 Zn(2+), Cd(2+), Ni(2+) and Cu(2+) metal ions, which reduced the emission intensity under identical conditions. Graphical Abstract 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 Zn(2+), Cd(2+), Ni(2+) and Cu(2+) ions under identical conditions.
authors.affiliation: Health Services Vocational School & ASUBTAM BioNanoTech Lab., Aksaray University, TR-68100, Aksaray, Turkey. melekalgi@aksaray.edu.tr.
authors.forename: Melek Pamuk
authors.initials: MP
authors.lastname: Algi
mesh_terms: D005456:Fluorescent Dyes / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D006997:Hypochlorous Acid / Q000032:analysis* / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D010618:Phenanthrolines / Q000737:chemistry*; D013050:Spectrometry, Fluorescence
chemical_list: D005456:Fluorescent Dyes; D008670:Metals; D010618:Phenanthrolines; D006997:Hypochlorous Acid; C025205:1,10-phenanthroline
keywords: 1,10-phenanthroline; Fluorescence; Hypochlorite; Probe