Water-Soluble Iridium(III) Complexes Containing Tetraethylene-Glycol-Derivatized Bipyridine Ligands for...

Four cationic heteroleptic iridium(III) complexes containing a 2,2'-bipyridine (bpy) ligand with one or two tetraethylene glycol (TEG) groups attached in the 4 or 4,4' positions were synthesized to create new water-soluble electrogenerated chemiluminescence (ECL) luminophores bearing a convenient point of attachment for the development of ECL-labels. The novel TEG-derivatized bipyridines were incorporated into [Ir(C^∧N)₂(R-bpy-R')]Cl complexes, where C^∧N = 2-phenylpyridine anion (ppy) or 2-phenylbenzo[d]thiazole anion (bt), through reaction with commercially available ([Ir(C^∧N)₂(μ-Cl)]₂ dimers. The novel [Ir(C^∧N)₂(Me-bpy-TEG)]Cl and [Ir(C^∧N)₂(TEG-bpy-TEG)]Cl complexes in aqueous solution largely retained the redox potentials and emission spectra of the parent [Ir(C^∧N)₂(Me-bpy-Me)]PF₆ (where Me-bpy-Me = 4,4'methyl-2,2'-bipyridine) luminophores in acetonitrile, and exhibited ECL intensities similar to those of [Ru(bpy)₃]²⁺ and the analogous [Ir(C^∧N)₂(pt-TEG]Cl complexes (where pt-TEG = 1-(TEG)-4-(2-pyridyl)-1,2,3-triazole). These complexes can be readily adapted for bioconjugation and considering the spectral distributions of [Ir(ppy)₂(Me-bpy-TEG)]⁺ and [Ir(ppy)₂(pt-TEG)]⁺, show a viable strategy to create ECL-labels with different emission colors from the same commercial [Ir(ppy)₂(μ-Cl)]₂ precursor.