Iridium complex with phosphorescent ion pair structure as well as preparation method and application of iridium complex

A technology of iridium complex and ion pair, which is used in medical preparations containing active ingredients, indium organic compounds, platinum group organic compounds, etc.

Active Publication Date: 2017-10-24
NANJING UNIV OF POSTS & TELECOMM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the use of phosphorescent ion-pair iridium complexes as photosensitizers in the field of photodynamic therapy.

Method used

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  • Iridium complex with phosphorescent ion pair structure as well as preparation method and application of iridium complex
  • Iridium complex with phosphorescent ion pair structure as well as preparation method and application of iridium complex
  • Iridium complex with phosphorescent ion pair structure as well as preparation method and application of iridium complex

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Preparation of cationic iridium complex Ir-1:

[0031] As shown in the figure above, as shown in Reaction i, weigh benzaldehyde (1mmol), 2-acetylpyridine (4mmol), sodium hydroxide (4.2mmol), ammonia water (3mmol) into the reaction flask, add ethanol, 25 ℃ Stir magnetically for 12 hours. After the reaction, the precipitate is filtered, and the recrystallized product obtained by recrystallization with ethanol is phenyl terpyridine, which can be directly put into the next reaction after drying. 1 H NMR (400MHz, CDCl 3 )δ8.76–8.71(m,4H),8.67(t,J=6.4Hz,2H),7.94–7.85(m,4H),7.49(dt,J=20.0,4.9Hz,3H),7.35(dt , J=10.8, 5.2Hz, 2H).

[0032] As shown in reaction ii, weigh phenyl terpyridine (1mmol) and IrCl 3 ·3H 2 O (1mmol) was mixed and put into a three-necked bottle, and the double-row tube was vacuumized-nitrogen gas-vacuumized, and the cycle was repeated three times, and finally the whole reaction system was protected by nitrogen gas. Ethylene glycol ether was injected i...

Embodiment 2

[0036] Preparation of anionic iridium complex Ir-2:

[0037] As shown in reaction ⅳ, weigh phenylpyridine (2.5mmol) and IrCl 3 ·3H 2O (1mmol) was mixed and put into a three-necked bottle, and the double-row tube was vacuumized-nitrogen gas-vacuumized, and the cycle was repeated three times, and finally the whole reaction system was protected by nitrogen gas. A mixture of ethylene glycol ether and water with a volume ratio of 3:1 was injected into the reaction system, the temperature was raised to 110° C., and the reaction was performed under magnetic stirring for 24 hours. After the reaction, cool the system to room temperature, filter the precipitate, and wash with ethanol and water. The obtained solid product is the phenylpyridine iridium dichloro bridge, which can be directly put into the next reaction after drying.

[0038] As shown in reaction v, weigh phenylpyridinium iridium dichloro bridge (1mmol) and tetrabutylcyanamide (2.3mmol) and mix them into the reaction flask...

Embodiment 3

[0041] Preparation of phosphorescent ion pair iridium complex Ir-3:

[0042] As shown in reaction ⅵ, weigh cationic iridium complex Ir-1 (1mmol) and anionic iridium complex Ir-2 (3mmol) and mix them into the reaction flask, inject acetone into the system, and control the temperature at 25°C. After stirring and reacting for 4 hours, a small amount of water was injected into the system and stirred for 1 minute, then suction filtered, and the solid product was recrystallized through acetone and ether to obtain a solid product which was the iridium complex Ir-3. 1 H NMR (400MHz, DMSO-d 6 )δ9.68(s,2H),9.61(s,2H), 9.30(s,1H),9.27–9.18(m,4H),8.59(d,J=8.5Hz,1H),8.44(d,J =7.6 ​​Hz, 2H), 8.37(dt, J=14.5, 7.4Hz, 5H), 8.05(d, J=8.9Hz, 1H), 7.99(d, J=5.1Hz, 2H), 7.95(d, J =5.3Hz, 2H), 7.84(t, J=7.7Hz, 2H), 7.76(dd, J=12.8, 7.9Hz, 2H), 7.59(dt, J=12.6, 7.0Hz, 5H), 7.40(t ,J=7.6Hz, 1H),4.58(t,J=7.0Hz,2H),1.94–1.74(m,2H),1.50–1.17(m,6H), 0.82(t,J=7.1Hz,3H) .

[0043]

[0044] Same as ...

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Abstract

The invention discloses an iridium complex with a phosphorescent ion pair structure as well as a preparation method and an application of the iridium complex. The iridium complex is a phosphorescent anion and cation type soft salt iridium complex formed by bonding of a terpyridyl cation complex and a cation complex, wherein the cation complex contains a cyclometalated ligand, and a metal center and cyanogen are taken as auxiliary ligands. The structural general formula of the iridium complex is as shown in the specification. The iridium complex with the phosphorescent ion pair structure is capable of generating singlet oxygen under the radiation of white light, can be applied to the photodynamics treatment field and has very good application prospects in the photodynamics treatment.

Description

technical field [0001] The invention relates to an iridium complex with a phosphorescent ion pair structure, a preparation method and application thereof, and belongs to the technical field of organic photoelectric functional materials. Background technique [0002] Photodynamic therapy (PDT) is a non-invasive or minimally invasive, non-thermal treatment method that uses photochemical reactions to target tissues and tumor cells. PDT is a cold photochemical reaction whose basic elements are oxygen, a photosensitizer, and visible light (laser is commonly used). First, the tumor tissue selectively absorbs the photosensitizer, and then chooses a laser with an appropriate wavelength to irradiate the local area. The photosensitizer can absorb the energy of the photons of the light source to reach the excited singlet state, and the photosensitizer passes through the gap from the excited singlet state to the photosensitizer. Excite the triplet state. Because the photosensitizer ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C09K11/06A61K41/00A61P35/00
CPCA61K41/0057C07F15/0033C07F15/004C09K11/06C09K2211/185
Inventor 赵强张书军马云刘淑娟黄维
Owner NANJING UNIV OF POSTS & TELECOMM
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