Eight 1,10-phenanthrolines bearing one or two 2-(1-adamantyloxy)ethylamino substituents attached to different positions of the heterocyclic core were prepared according to SN Ar or palladium-catalyzed amination reactions. Their reaction with cis-Ru(bpy)2 Cl2 (bpy=2,2'-bipyridine) was investigated and Ru(bpy)2 (L)(PF6 )2 (phen=1,10-phenanthroline) (L=amino-substituted 1,10-phenanthroline) complexes were obtained in good yields. The electronic structure and emissive properties of these complexes are strongly dependent on the position of the amino substituent in the heterocycle. Emission bands of the complexes bearing 2- and 4-substituted 1,10-phenanthroline ligands are red-shifted (up to 56 nm) and less intense compared to that of the parent [Ru(phen)(bpy)2 ](PF6 )2 . In contrast, the introduction of the substituent in 3- or 5-position of 1,10-phenanthroline ring induces only small decrease of luminescence and the brightness of the complex with the 3-substituted ligand is comparable to that of the parent complex.
Keywords: 1,10-phenanthrolines; amination; catalysis; luminescence; ruthenium.
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