Ruthenium(II) Complexes with (3-Polyamino)phenanthrolines: Synthesis and Application in Sensing of Cu(II) Ions
2022
Anton S. Abel | Alexei D. Averin | Andrey V. Cheprakov | Irina P. Beletskaya | Michel Meyer | Alla Bessmertnykh-Lemeune
This work deals with the development of water-soluble optical sensors based on ruthenium(II) tris(diimine) complexes that exhibit high molar absorptivity and are emissive in aqueous media. Palladium-catalyzed arylation of polyamines with 3-bromo-1,10-phenanthroline (Brphen) and [Ru(bpy)<sub>2</sub>(Brphen)](PF<sub>6</sub>)<sub>2</sub> (bpy = 2,2’-bipyridine) was explored to prepare Ru<sup>2+</sup> complexes with 1,10-phenanthrolines (phen) substituted by linear polyamines (PAs) at position 3 of the heterocycle ([Ru(bpy)<sub>2</sub>(phen–PA)](PF<sub>6</sub>)<sub>2</sub>). The most convenient synthetic pathway leading to the target molecular probes includes the preparation of phen–PA ligands, followed by ruthenium complexation using <i>cis</i>-Ru(bpy)<sub>2</sub>Cl<sub>2</sub>. Complexes bearing a polyamine chain directly linked to phenanthroline core are emissive in aqueous media and their quantum yields are comparable to that of parent [Ru(bpy)<sub>3</sub>](PF<sub>6</sub>)<sub>2</sub>. Their structure can be easily adapted for detection of various analytes by modification of amine groups. As an example, we prepared the emissive complex <b>Ru(N<sub>2</sub>P<sub>2</sub>phen)</b> which is suitable for the dual channel (spectrophotometry and luminescence (ON–OFF probe)) selective detection of Cu<sup>2+</sup> ions at the physiological pH levels with limits of detection (LOD) by spectrophotometry and fluorescence spectroscopy equal to 9 and 6 μM, respectively, that is lower than the action level in drinking water for copper as prescribed by the US Environmental Protection Agency.
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