Bifunctional Luminescent Rhenium(I) Complexes Containing an Extended Planar Diimine Ligand and a Biotin Moiety
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Abstract
We report the synthesis, characterization, and photophysical and electrochemical properties of four bifunctional luminescent rhenium(I) complexes that contain an extended planar diimine ligand and a biotin moiety, [Re(N-N)(CO)3(L)](PF6) (N-N = dipyrido[3,2-a:2‘,3‘-c]phenazine, dppz; L = 4-((biotinamido)methyl)pyridine (py-CH2NH-biotin; 1), 4-(N-((6-biotinamido)hexanoyl)aminomethyl)pyridine, (py-CH2NHCOC5H10NH-biotin; 2); N-N = benzo[i]dipyrido[3,2-a:2‘,3‘-c]phenazine, dppn; L = py-CH2NH-biotin (3), py-CH2NHCOC5H10NH-biotin (4)). Upon irradiation, complexes 1−4 exhibit intense and long-lived emission in deoxygenated fluid solutions at 298 K and in low-temperature glass. The luminescence is assigned to a triplet intraligand (3IL) (π → π*) (diimine) excited state. However, the excited state of the dppn complexes 3 and 4 is likely to possess substantial triplet metal-to-ligand charge-transfer (3MLCT) (dπ(Re) → π*(dppn)) character. The interactions of these complexes with double-stranded calf thymus DNA have been studied by absorption and emission titrations. The binding of the complexes to avidin has also been investigated by HABA assays and emission titrations.
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