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A series of 5,5?-disubstituted 2,2?-bipyridines and their corresponding tris complexes with ruthenium(II) have been synthesized. The substituents used (ketone, ester, nitrile, imide, and two amides) are all electron withdrawing in nature and, with one exception, contain a carbonyl group in the position alpha to the bipyridine ring. The reduction potentials of the free ligands and ruthenium complexes have been determined by cyclic voltammetry and are correlated with the Hammett rho constants of the substituents. Finally, the electron- withdrawing nature of these substituents shifts the reduction potentials of each complex sufficiently positive that up to six stable ligand-based reductions are observable. In these reduced oxidation states, all of the complexes display multicolor electrochromism.
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Reference：
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI