Synthesis of 1,3-dihydro-1,1,3,3-tetramethyl-7,8-diazacyclopenta[1]phenanthren-2-one chelated ruthenium(II) complexes and their electrochemiluminescent characteristics

ORGN 356

Byeong Hyo Kim1, Jung Hyo Min1, Hak Mook Kim1, Do Nam Lee1, Young Moo Jun1, Han Nim Choi2, and Won-Yong Lee2. (1) Department of Chemistry, Kwangwoon University, 447-1 Nowon-ku Wolgye-dong, Seoul, 139-701, South Korea, (2) Department of Chemistry, Yonsei University, Seoul, 120-749, South Korea
Transition metal complexes based electrochemiluminescence (ECL) have been used for the analysis of a wide range of compounds. It is known that Ru(o-phen)32+ and their derivatives produce more intense emission than Ru(bpy)32+. To develop more sensitive new ECL complexes, we become interest in synthesizing the new α-diimine ligand which contains the o-phenanthroline analogy. Thus we synthesized the new ligand, i.e 1,3-dihydro-1,1,3,3-tetramethyl-7,8-diazacyclopenta[1]phenanthren-2-one (DTDP) and it was used for the synthesis of the new Ru (II) complexes such as [Ru(DTDP)n(L)3-n]2+ [L=2,2′-bipyridyl, 4,4′-dimethyl-2,2′-bipyridyl, 2,2′-bipyridine-4,4′-dicarboxaldehyde, o-phenanthroline, 5-chloro-1,10-phenanthroline, 4-carboxylmethyl-4′-methyl-2,2′-bipyridyl, 4-(3-carboxylpropyl)-4′-methyl-2,2′-bipyridyl]. It was found that Ru(II) complexes containing DTDP ligand showed the foremost ECL property compared to other known ECL Ru complexes.