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In this work the synthesis, photochemistry, and streptavidin interaction of new [Ru(tpy)(bpy)(SRR′)](PF 6 ) 2  complexes where the R′ group contains a free biotin ligand, are described. Two different ligands SRR′ were investigated: An asymmetric ligand  1  where the Ru‐bound thioether is a  N ‐acetylmethionine moiety linked to the free biotin fragment via a triethylene glycol spacer and a symmetrical ligand  2  containing two identical biotin moieties. The coordination of these two ligands to the precursor [Ru(tpy)(bpy)Cl]Cl was studied in water at 80 °C. In such conditions the coordination of the asymmetric ligand  1  occurred under thermodynamic control. After the reaction, a mononuclear and a binuclear complex were isolated. In the mononuclear complex, the ratio of methionine‐ {[ 6 ](PF 6 ) 2 } vs. biotin‐bound {[ 7 ](PF 6 ) 2 } regioisomer was 5.3 and the free biotin fragment of [ 6 ](PF 6 ) 2  allowed to purify it from its isomer [ 7 ](PF 6 ) 2  at small scales using avidin affinity chromatography. Coordination of the symmetrical ligand  2  afforded [Ru(tpy)(bpy)( 2 )](PF 6 ) 2  {[ 8 ](PF 6 ) 2 } in synthetically useful scales (100 mg), good yield (82 %), and without traces of the binuclear impurity. In this complex, one of the biotin remains free whereas the second one is coordinated to ruthenium. Photochemical release of ligand  2  from [ 8 ](PF 6 ) 2  occurred upon blue light irradiation (465 nm) with a photosubstitution quantum yield of 0.011 that was independent of the binding of streptavidin to the free biotin ligand.

Synthesis and Avidin Binding of Ruthenium Complexes Functionalized with a Light‐Cleavable Free Biotin Moiety