Photofunctional Cyclometalated Iridium(III) Polypyridine Complexes Bearing a Perfluorobiphenyl Moiety for Bioconjugation, Bioimaging, and Phototherapeutic Applications.

In this article, we report the design, synthesis, and characterization of a series of cyclometalated iridium(III) polypyridine complexes containing a perfluorobiphenyl (PFBP) moiety [Ir(N^C)(bpy-PFBP)](PF) (bpy-PFBP = 4-(-(perfluoro-(1,1'-biphenyl)-4-yl)--mercaptoethylaminocarbonyloxymethyl)-4'-methyl-2,2'-bipyridine; HN^C = 2-phenylpyridine (Hppy) (), 2-(4-hydroxymethylphenyl)pyridine (Hppy-CHOH) (), 2-((1,1'-biphenyl)-4-yl)pyridine (Hpppy) (), 2-((4'-hydroxymethyl-1,1'-biphenyl)-4-yl)pyridine (Hpppy-CHOH) (), 2-phenylquinoline (Hpq) (), 2-(4-hydroxymethylphenyl)quinoline (Hpq-CHOH) ()). Their PFBP-free counterparts [Ir(N^C)(bpy-C4)](PF) (bpy-C4 = 4-(--butylaminocarbonyloxymethyl)-4'-methyl-2,2'-bipyridine; HN^C = Hppy (), Hppy-CHOH (), Hpppy (), Hpppy-CHOH (), Hpq (), Hpq-CHOH ()) were also prepared for comparison studies. Upon irradiation, all the complexes displayed intense and long-lived greenish-yellow to orange luminescence in solutions under ambient conditions and in low-temperature alcohol glass.