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4,5-diazafluorene (daf) and 9,9'-dimethyl-4,5-diazafluorene (Me 2 daf) are structurally similar to the important ligand 2,2'-bipyridine (bpy), but significantly less is known about the redox and spectroscopic properties of metal complexes containing Me 2 daf as a ligand than those containing bpy. New complexes Mn(CO) 3 Br(daf) ( 2 ), Mn(CO) 3 Br(Me 2 daf) ( 3 ), and [Ru(Me 2 daf) 3 ](PF 6 ) 2 ( 5 ) have been prepared and fully characterized to understand the influence of the Me 2 daf framework on their chemical and electrochemical properties. Structural data for 2 , 3 , and 5 from single-crystal X-ray diffraction analysis reveal a distinctive widening of the daf and Me 2 daf chelate angles in comparison to the analogous Mn(CO) 3 (bpy)Br ( 1 ) and [Ru(bpy) 3 ] 2+ ( 4 ) complexes. Electronic absorption data for these complexes confirm the electronic similarity of daf, Me 2 daf, and bpy, as spectra are dominated in each case by metal-to-ligand charge transfer bands in the visible region. However, the electrochemical properties of 2 , 3 , and 5 reveal that the redox-active Me 2 daf framework in 3 and 5 undergoes reduction at a slightly more negative potential than that of bpy in 1 and 4 . Taken together, the results indicate that Me 2 daf could be useful for preparation of a variety of new redox-active compounds, as it retains the useful redox-active nature of bpy but lacks the acidic, benzylic C-H bonds that can induce secondary reactivity in complexes bearing daf.

4,5-Diazafluorene and 9,9’-Dimethyl-4,5-Diazafluorene as Ligands Supporting Redox-Active Mn and Ru Complexes