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Palladium‐Catalyzed C−H Bond Arylation of Cyclometalated Difluorinated 2‐Arylisoquinolinyl Iridium(III) Complexes
Author(s) -
Peng Marie,
Lin Jinqiang,
Lu Wei,
Roisnel Thierry,
Guerchais Véronique,
Doucet Henri,
Soulé JeanFrançois
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202102006
Subject(s) - iridium , aryl , palladium , chemistry , surface modification , trifluoromethyl , catalysis , nitrile , phosphorescence , medicinal chemistry , electrochemistry , combinatorial chemistry , polymer chemistry , organic chemistry , fluorescence , alkyl , physics , quantum mechanics , electrode
The utility of C−H bond functionalization of metalated ligands for the elaboration of aryl‐functionalized difluorinated‐1‐arylisoquinolinyl Ir(III) complexes has been explored. Bis[(3,5‐difluorophenyl)isoquinolinyl](2,2,6,6‐tetramethyl‐3,5‐heptanedionato) iridium(III) undergoes Pd‐catalyzed C−H bond arylation with aryl bromides. The reaction regioselectively occurred at the C−H bond flanked by the two fluorine atoms of the difluoroaryl unit, and on both cyclometalated ligands. This post‐functionalization gives a straightforward access to modified complexes in only one manipulation and allows to introduce thermally sensitive functional groups, such as trifluoromethyl, nitrile, benzoyl, or ester. The X‐ray crystallography, photophysical, and electrochemical properties of the diarylated complexes were investigated. Whatever the nature of the incorporated substituted aryl groups is, all obtained complexes emit red phosphorescence (622–632 nm) with similar lifetimes (1.9–2 μs).