Iridium anticancer complex containing phosphinimine bidentate chelate ligand and its preparation method and application
A technology for chelating ligands and complexes, which can be used in organic chemistry methods, chemical instruments and methods, organic chemistry, etc., and can solve problems such as the existence of toxic and side effects
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Embodiment 1
[0054]39.8 mg of iridium dimer (R1Is methyl), 1-(2-(diphenylphosphino)phenyl)-N-phenylimine (36.5mg, 0.10 mmol) in a 50 mL round bottom flask, add 20mL CH2Cl2 Stir at room temperature for 24 h, then 110.4mg KPF6Was added and continued to stir for 2 h, spin-dry the solvent on a rotary evaporator, and use an appropriate amount of CH2Cl2The solid was dissolved, filtered into a reagent bottle, and 20 mL of n-hexane was slowly added along the bottle wall to separate the layers and recrystallized by diffusion method to obtain 47 mg of yellow solid product (yield, 54%).1H NMR (500 MHz, DMSO) δ 8.62 (d,J = 2.4 Hz, 1H,HC=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).31P NMR (202 MHz, DMSO) δ 11.41 (P(Ph)2), -133.65 (PF6), -137.17 (PF6), -140.68 (PF6), -144.19 (PF6), -147.71 (PF6), -151.22 (PF6...
Embodiment 2
[0056]39.8 mg of iridium dimer (R1Is methyl), N-(2,6-dimethylbenzene)-1-(2-(diphenylphosphino)phenyl)imine (39.3 mg, 0.10 mmol) in a 50 mL round bottom flask , Add 20mL CH2Cl2 Stir at room temperature for 24 h, then 110.4 mg KPF6Was added and continued to stir for 2 h, spin-dry the solvent on a rotary evaporator, and use an appropriate amount of CH2Cl2The solid was dissolved, filtered into a reagent bottle, 20 mL of n-hexane was slowly added along the bottle wall to separate the layers and recrystallized by diffusion method to obtain 63 mg of yellow solid product (yield, 70%).1H NMR (500 MHz, CDCl3) δ 8.07 (d, J = 3.2 Hz, 1H,HC=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-CH3), 1.37 (s, 3H,o-aniline-CH3), 1.16 (d, J = 2.4 Hz, 15H,Cp*-H).31P NMR (202 MHz, CDCl3) δ 6.64 (P(Ph)2), -133.94 (PF6...
Embodiment 3
[0058]39.8 mg of iridium dimer (R1Is methyl), N-(2,6-diisopropylbenzene)-1-(2-(diphenylphosphino)phenyl)imine (45.0 mg, 0.10 mmol) in a 50 mL round bottom flask Add 20mL CH2Cl2 Stir at room temperature for 24h, then 110.4 mg KPF6Was added and continued to stir for 2 h, spin-dry the solvent on a rotary evaporator, and use an appropriate amount of CH2Cl2The solid was dissolved, filtered into a reagent bottle, 20 mL of n-hexane was slowly added along the wall of the bottle to separate the layers and recrystallized by diffusion method to obtain 44 mg of yellow solid product (yield, 46%).1H NMR (500 MHz, CDCl3) δ 8.07 (d,J = 2.9 Hz, 1H,HC=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,iPr-CH), 2.19 – 2.12 (m, 1H,iPr-CH), 1.38 (d,J = 6.8 Hz, 3H,iPr-CH3), 1.19(d,J = 2.4 Hz, 15H, Cp*-H), 1.10 (d,J = 6.6 Hz, 3H,iPr-CH3),...
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