Soluble phosphorescent iridium(III) complexes from cinchonine-derived ligands

Wen Hua Zhang, Xin Hai Zhang, Ai Ling Tan, M. Anna Yong, David J. Young, T. S. Andy Hor

Research output: Contribution to journalArticlepeer-review


Cinchonine-derived complexes Ir(L2) 2(acac) (3), Ir(L2) 2(dbm) (4), [Ir-(L1)2(bipy)][PF6] (5), [Ir(L1)2(phen)][PF6] (6), [Ir(L1)2(dppe)][PF6] (7), [Ir-(L2) 2(bipy)][PF6] (8), [Ir(L2) 2(phen)][PF6] (9), and [Ir(L2) 2(dppe)][PF6] (10) (L1 =2-phenyl-9-O-benzyl-10,11-dihydrocinchonine-N,C; L2 = 2-(2,4-difluorophenyl)-9- O-benzyl-10,11-dihydrocinchonine-N,C; acac = acetylacetonate; dbm = dibenzoylmethane; bipy =2,2-bipyridine; phen = 1,10-phenanthroline; dppe = (Z)-1,2-bis(diphenylphosphino)ethene) are highly soluble in common organic solvents and phosphoresce with emission wavelengths from orange to green (583529 nm) and internal quantum efficiencies from 4 to 24%. The emission is blue-shifted for the neutral auxiliary ligands and/or by incorporation of fluorine into the alkaloid-based chromophore. An unprecedented regiospecific monohydrodefluorination of L2, giving 2-(4-fluorophenyl)-9-O-benzyl-10,11- dihydrocinchonine (L2), occurred during the synthesis of 3 and 4.

Original languageEnglish
Pages (from-to)553-559
Number of pages7
Issue number2
Publication statusPublished - 23 Jan 2012
Externally publishedYes


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