Synthesis and Properties of Tetrasubstituted 1,10-Phenanthrolines and Their Ruthenium Complexes



The synthesis and the photophysical properties of a series of tetrasubstituted phenanthroline (phen) ruthenium complexes of the type [Ru(tbbpy)2(phen-R4)]2+ (tbbpy = 4,4′-di-tert-butyl-2,2′-bipyridine; phen = 1,10-phenanthroline; R represents the substitution at 3-, 5-, 6- and 8-positions with phenyl, 4-tert-butylphenyl and para-biphenyl) and of a homoleptic [Ru(phen-R′4)3]2+ (R′ = 4-tert-butylphenyl) are described. The phen-R4 ligands were obtained in high yields usingSuzuki-type coupling reactions. The solid-state structure of 3,5,6,8-tetraphenylphenanthroline is reported. The investigation of the photophysical properties of the free ligands reveals a pronounced effect of the aryl substitution on absorption and emission properties. These properties are mirrored in the corresponding complexes, which possess room-temperature emission lifetimes of up to 2833 ns.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)