Phenyl quinoline derivative iridium (III) complex based on piperidine or morpholine methylene substitution, and preparation method and application thereof

A technology of morpholine methylene and phenylquinoline iridium, applied in the field of preparation of phenylquinoline iridium complexes, to achieve the effects of reducing signal-to-noise ratio, excellent pH value response properties, and improving detection accuracy

Active Publication Date: 2015-09-16
NANJING UNIV OF POSTS & TELECOMM
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  • Abstract
  • Description
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Problems solved by technology

However, as far as we know, almost no phosphorescent pH probes based on iridium complexes have been reported. Therefore, the s

Method used

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  • Phenyl quinoline derivative iridium (III) complex based on piperidine or morpholine methylene substitution, and preparation method and application thereof
  • Phenyl quinoline derivative iridium (III) complex based on piperidine or morpholine methylene substitution, and preparation method and application thereof
  • Phenyl quinoline derivative iridium (III) complex based on piperidine or morpholine methylene substitution, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1: Complex [Ir(PQ-C-N) 2 (bpy)] + PF 6 - Synthesis

[0037]

[0038] (1) Synthesis of 2-bromo-4-bromomethylquinoline

[0039] Take 1.11g of 2-bromo-4-methylquinoline, 0.98g of N-bromosuccinimide (NBS), 240mg of benzoyl peroxide (BPO), and 50mL of carbon tetrachloride, and add them to the belt stirring In a three-necked flask with nitrogen gas, reflux at 80°C for 24h, spin dry under reduced pressure, and use petroleum ether / ethyl acetate (V:V=100:1) column chromatography to obtain a colorless crystalline powder with a yield of 49 %. 1 H NMR (600MHz, DMSO-d 6 )δ(ppm): 8.24(d; J=8.40Hz; 1H); 8.01(d; J=8.40Hz; 1H); 7.89(s; 1H); 7.84(t; J=7.20Hz; 1H); 7.76 (t; J = 7.20 Hz; 1H); 5.15 (s; 2H).

[0040] (2) Synthesis of 2-bromo-4-(piperidin-1-ylmethyl)quinoline

[0041] Take 3.01g of 2-bromo-4-bromomethylquinoline, 0.90g of piperidine, 5g of anhydrous potassium carbonate, and 100mL of anhydrous acetonitrile, and add them in turn to a three-necked flask wi...

Embodiment 2

[0051] Embodiment 2: Complex [Ir(PQ-C-NO) 2 (bpy)] + PF 6 - Synthesis

[0052]

[0053] (1) Synthesis of 2-bromo-4-(morpholin-1-ylmethyl)quinoline

[0054] Take 3.01g of 2-bromo-4-bromomethylquinoline, 0.91g of morpholine, 5g of anhydrous potassium carbonate, and 100mL of anhydrous acetonitrile, and add them in turn to a three-necked flask with a stirring bar, react at 25°C for 24h, and then depressurize Spin to dry, and use petroleum ether / ethyl acetate (V:V=10:1) column chromatography to obtain a colorless crystalline powder with a yield of 90%.

[0055] (2) Synthesis of 2-phenyl-4-(morpholin-1-ylmethyl)quinoline

[0056] Take 2-bromo-4-(morpholin-1-ylmethyl)quinoline 1.29g, phenylboronic acid 0.52g, Pd(PPh 3 ) 4 160mg, 10mL saturated aqueous sodium carbonate solution, 10mL absolute ethanol, and 30mL toluene were added to a three-necked flask with a stirring bar in turn, nitrogen was passed, and after reflux reaction for 14 hours, after washing and drying, spin-dry...

Embodiment 3

[0064] Embodiment 3: Complex [Ir(4FPQ-C-N) 2 (bpy)] + PF 6 - Synthesis

[0065]

[0066] (1) Synthesis of 2-(4-fluorophenyl)-4-(piperidin-1-ylmethyl)quinoline

[0067] Get 2-bromo-4-(piperidin-1-ylmethyl) quinoline 1.29g synthesized in Example 1, 591mg of 4-fluorophenylboronic acid, Pd(PPh 3 ) 4 160mg, 10mL saturated aqueous sodium carbonate solution, 10mL absolute ethanol, and 30mL toluene were added to a three-necked flask with a stirring bar in turn, nitrogen was passed, and after reflux reaction for 14 hours, after washing and drying, spin-drying under reduced pressure, and using petroleum ether / ethyl acetate (V:V=10:1) Column chromatography yielded a white crystalline powder with a yield of 91%. 1 H NMR (400MHz, CDCl 3 )δ(ppm): 8.23(dd; J=0.80Hz; J=8.40Hz; 1H); 8.21-8.16(m; 2H); 8.16(dd; J=0.40Hz; J=8.40Hz; 1H); 7.90 (t; J=0.40Hz; 1H); 7.71(ddd; J=1.60Hz; J=6.80Hz; J=8.40Hz; 1H); 7.53(ddd; J=1.20Hz; J=6.80Hz; J=8.40 Hz; 1H); 7.24-7.18(m; 2H); 3.93(d; J=0.40Hz;...

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Abstract

The invention relates to a phenyl quinoline derivative iridium (III) complex based on piperidine or morpholine methylene substitution, and relates to the technical field of organic photoelectric materials. The complex is composed of a cyclometalated C^N bidentate ligand substituted by piperidine or morpholine through methylene connection, central metal iridium (III) ion and 2,2'-bipyridyl. The complex has a structural general formula as the following. According to the invention, a piperidine or morpholine methylene-substituted phenyl quinoline derivative C^N bidentate ligand is subjected to a reaction with iridium trichloride trihydrate, such that a iridium (III) chloro-bridged dimer with a corresponding ligand is obtained; the dimer is further subjected to a reaction with 2,2'-bipyridyl; and the complex is prepared through ion exchange. The iridium (III) complex provided by the invention has a good application prospect in the fields of intracellular pH value testing, imaging and marking.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric materials, in particular to a method for preparing a phenylquinoline iridium (III) complex substituted by piperidine or morpholine methylene and its intracellular pH value detection, imaging, labeling and Applications in the field of organic optoelectronic devices. Background technique [0002] In recent years, with the continuous development of biochemistry, the research on the active species in living cells, cell signal transduction and cell apoptosis has become more and more in-depth. Intracellular pH plays an important role in many physiological processes, including cell proliferation, apoptosis, ion transport, endocytosis, and muscle contraction. In addition, monitoring changes in intracellular pH is also particularly important for studying cellular internalization pathways, such as phagocytosis, endocytosis, etc. Changes in intracellular pH also affect the nervous system by a...

Claims

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Application Information

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IPC IPC(8): C07F15/00C09K11/06H01L51/54G01N21/64
CPCG01N21/64C09K11/06C07F15/0033C09K2211/185H10K85/342H10K50/11
Inventor 赵强黄维陶鹏许文娟刘淑娟
Owner NANJING UNIV OF POSTS & TELECOMM
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