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Herein we report four [Ir(NC)(2)(LL)](n+), n = 0,1 complexes (1-4) containing cyclometallated NC ligand (NCH = 1-phenyl-2-(4-(pyridin-2-yl)phenyl)-1H-phenanthro[9,10-d]imidazole) and various bidentate LL ligands (picolinic acid (1), 2,2 '-bipyridine (2), [2,2 '-bipyridine]-4,4 '-dicarboxylic acid (3), and sodium 4,4 ',4 '',4"'-(1,2-phenylenebis(phosphanetriyl))tetrabenzenesulfonate (4). The NCH ligand precursor and iridium complexes 1-4 were synthesized in good yield and characterized using chemical analysis, ESI mass spectrometry, and NMR spectroscopy. The solid-state structure of 2 was also determined by XRD analysis. The complexes display moderate to strong phosphorescence in the 550-670 nm range with the quantum yields up to 30% and lifetimes of the excited state up to 60 mu s in deoxygenated solution. Emission properties of 1-4 and NCH are strongly pH-dependent to give considerable variations in excitation and emission profiles accompanied by changes in emission efficiency and dynamics of the excited state. Density functional theory (DFT) and time-dependent density functional theory (TD DFT) calculations made it possible to assign the nature of emissive excited states in both deprotonated and protonated forms of these molecules. The complexes 3 and 4 internalize into living CHO-K1 cells, localize in cytoplasmic vesicles, primarily in lysosomes and acidified endosomes, and demonstrate relatively low toxicity, showing more than 80% cells viability up to the concentration of 10 mu M after 24 h incubation. Phosphorescence lifetime imaging microscopy (PLIM) experiments in these cells display lifetime distribution, the conversion of which into pH values using calibration curves gives the magnitudes of this parameter compatible with the physiologically relevant interval of the cell compartments pH.
Original language | English |
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Article number | 232 |
Number of pages | 20 |
Journal | Molecules |
Volume | 27 |
Issue number | 1 |
Early online date | Dec 2021 |
DOIs | |
State | Published - 1 Jan 2022 |
ID: 91172052