Iridium anticancer complex containing phosphinimine dual-teeth chelating ligand and preparing method and application thereof
A technology of chelating ligands and complexes, applied in organic chemistry methods, chemical instruments and methods, organic chemistry, etc., can solve problems such as the existence of toxic and side effects
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Embodiment 1
[0054] 39.8 mg iridium dimer (R 1 is methyl), 1-(2-(diphenylphosphanyl)phenyl)-N-phenylmethanimine (36.5 mg, 0.10 mmol) was placed in a 50 mL round bottom flask, and 20 mL CH 2 Cl 2 Stir at room temperature for 24 h, then 110.4 mg KPF 6 was added and continued to stir for 2 h, the solvent was spin-dried on a rotary evaporator, and an appropriate amount of CH 2 Cl 2 Dissolve the solid, filter it into a reagent bottle, slowly add 20 mL of n-hexane along the wall of the bottle to separate layers, and recrystallize by diffusion method to obtain 47 mg of a yellow solid product (yield, 54%). 1 H NMR (500 MHz, DMSO) δ 8.62 (d, J = 2.4 Hz, 1H, H C=N), 7.87 – 7.80 (m, 3H, aryl- H ), 7.72 (ddt, J = 18.3, 15.9,7.8 Hz, 11H, aryl- H ), 7.62 (t, J = 7.6 Hz, 1H, aryl- H ), 7.49 (dd, J = 10.6,7.8 Hz, 1H, aryl- H ), 7.41 (t, J = 7.5 Hz, 1H, aryl- H ), 7.12 (d, J = 7.7 Hz, 2H, aryl- H ), 1.02 (d, J = 2.3 Hz, 15H, Cp*- H ). 31 P NMR (202 MHz, DMSO) δ 11.41( P (Ph) 2...
Embodiment 2
[0056] 39.8 mg iridium dimer (R 1 is methyl), N-(2,6-dimethylphenyl)-1-(2-(diphenylphosphanyl)phenyl)methanimine (39.3 mg, 0.10 mmol) was placed in a 50 mL round bottom flask, and 20 mL CH 2 Cl 2 Stir at room temperature for 24 h, then 110.4 mg KPF 6 was added and continued to stir for 2 h, the solvent was spin-dried on a rotary evaporator, and an appropriate amount of CH 2 Cl 2 Dissolve the solid, filter it into a reagent bottle, slowly add 20 mL of n-hexane along the wall of the bottle to separate layers, and recrystallize by diffusion method to obtain 63 mg of a yellow solid product (yield, 70%). 1 H NMR (500MHz, CDCl 3 ) δ 8.07 (d, J = 3.2 Hz, 1H, H C=N), 7.72 – 7.65 (m, 4H, aryl- H ),7.64 – 7.58 (m, 5H, aryl- H ), 7.54 (td, J = 8.0, 2.8 Hz, 2H, aryl- H ), 7.28 (d,J = 3.8 Hz, 1H, aryl- H ), 7.23 (s, 1H, aryl- H ), 7.18 (d, J = 6.9 Hz, 1H, aryl- H ), 7.07 – 7.00 (m, 3H, aryl- H ), 2.27 (s, 3H, o -aniline-C H 3 ), 1.37 (s, 3H, o -aniline-C H 3 ), 1.16 (d,...
Embodiment 3
[0058] 39.8 mg iridium dimer (R 1 is methyl), N-(2,6-diisopropylphenyl)-1-(2-(diphenylphosphanyl)phenyl)methanimine (45.0 mg, 0.10 mmol) was placed in a 50 mL round bottom flask, and 20 mL CH 2 Cl 2 Stir at room temperature for 24 h, then 110.4 mg KPF 6 was added and continued to stir for 2 h, the solvent was spin-dried on a rotary evaporator, and an appropriate amount of CH 2 Cl 2 Dissolve the solid, filter it into a reagent bottle, slowly add 20 mL of n-hexane along the wall of the bottle to separate layers, and recrystallize by diffusion method to obtain 44 mg of a yellow solid product (yield, 46%). 1 H NMR (500MHz, CDCl 3 ) δ 8.07 (d, J = 2.9 Hz, 1H, H C=N), 7.68 (tt, J = 14.9, 7.4 Hz, 5H, aryl- H ), 7.63 – 7.59 (m, 1H, aryl- H ), 7.51 (dd, J = 6.7, 4.6 Hz, 4H, aryl- H ),7.34 – 7.27 (m, 3H, aryl- H ), 7.24 (d, J = 7.8 Hz, 2H, aryl- H ), 7.16 – 7.03(m, 2H, aryl- H ), 3.46 – 3.43 (m, 1H, i Pr-C H ), 2.19 – 2.12 (m, 1H, i Pr-C H ),1.38 (d, J = 6.8Hz...
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