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We report the synthesis and characterization of new ruthenium and rhenium nucleosides [Ru(tolyl-acac) 2 (IMPy)-T] (tolyl-acac ) di(p-methylbenzonatemethane), IMPy ) 2′-iminomethylpyridine, T ) thymidine) ( 5) and [Re(CO) 3 -(IMPy)-T]Cl (9), respectively. Structural analysis of 9 shows that the incorporation of this metal complex causes minimal perturbation to the sugar backbone and the nucleobase. Eletrochemical (5, E 1/2 ) 0.265 V vs NHE; 9, E 1/2 ) 1.67 V vs NHE), absorption (5, λ max ) 600, 486 nm; 9, λ max ) 388 nm), and emission (9, λ max ) 770 nm, π ) 17 ns) data indicate that 5 and 9 are suitable probes for DNA-mediated ground-state electron-transfer studies. The separation and characterization of diastereoisomers of 5 and bipyridyl-based ruthenium nucleoside [Ru(bpy) 2 -(IMPy)-T] 2+ (7) are reported.