Easy Separation of Δ and Λ Isomers of Highly Luminescent [IrIII]-Cyclometalated Complexes Based on Chiral Phenol-Oxazoline Ancillary Ligands

A new class of neutral cyclometalated iridium(III) complexes with enantiomerically pure C1‐symmetric phenol‐oxazolines (3 a,b) have been synthetized in high yields and fully characterized. Resolution of the corresponding ΔR and ΛR or ΔS and ΛS isomers was easily achieved by conventional flash chroma...

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Bibliographic Details
Published in:Chemistry : a European journal 2012-07, Vol.18 (28), p.8765-8773
Main Authors: Marchi, Enrico, Sinisi, Riccardo, Bergamini, Giacomo, Tragni, Michele, Monari, Magda, Bandini, Marco, Ceroni, Paola
Format: Article
Language:English
Subjects:
Absorption
chiral ligands
circular dichroism
Emission
Helicity
iridium
Isomers
Ligands
Luminescence
phosphorescence
Separation
X-rays
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Summary:A new class of neutral cyclometalated iridium(III) complexes with enantiomerically pure C1‐symmetric phenol‐oxazolines (3 a,b) have been synthetized in high yields and fully characterized. Resolution of the corresponding ΔR and ΛR or ΔS and ΛS isomers was easily achieved by conventional flash chromatography. The corresponding Δ and Λ helicities have been confirmed by CD spectroscopy and X‐ray crystallography. Regarding the absorption and luminescence properties with unpolarized light, no significant difference between Δ and Λ isomers has been observed. A strong blue luminescence is observed for deaerated solutions of complexes 5 a and 5 b in CH3CN. Phox and hounds: Δ and Λ isomers of IrIII complexes based on 2‐phenyl‐pyridyl (ppy) cyclometalating ligands and chiral phenol‐oxazoline ancillary ligands (see figure) are readily available through simple separation on an achiral stationary phase. Blue luminescence, combined with an excellent emission quantum yield (Φem=0.80), is recorded for complexes with F2ppy ligands.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201200709