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

W H Zhang; X H Zhang; A L Tan; M Anna Yong; David James Young; T S Andy Hor

doi:10.1021/om200759d

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

Journal article

Peer reviewed

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

W H Zhang, X H Zhang, A L Tan, M Anna Yong, David James Young and T S Andy Hor

Organometallics, Vol.31(2), pp.553-559

2012

DOI: https://doi.org/10.1021/om200759d

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Abstract

1 ,10-phenanthroline

2 ,2-Bipyridine

acetylacetonates

auxiliary ligands

blue-shifted

dibenzoylmethane

emission wavelength

internal quantum efficiency

iridium complex

regiospecific

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. © 2012 American Chemical Society.

Details

Title: Soluble phosphorescent iridium(iii) complexes from cinchonine-derived ligands
Authors: W H Zhang (Author) - National University of Singapore, Singapore
X H Zhang (Author) - Institute of Materials Research and Engineering, Singapore
A L Tan (Author) - Universiti Brunei Darussalam, Brunei
M Anna Yong (Author) - Institute of Materials Research and Engineering, Singapore
David James Young (Author) - Universiti Brunei Darussalam, Brunei
T S Andy Hor (Author) - National University of Singapore, Singapore
Publication details: Organometallics, Vol.31(2), pp.553-559
Publisher: American Chemical Society
Date published: 2012
DOI: 10.1021/om200759d
ISSN: 0276-7333
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99449581202621
Output Type: Journal article

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