Iridium(iii) complexes based on 2-(4-(dimidylboron)phenyl)pyridine ligands and their preparation methods and applications

A technology of micky boron and complexes, which is applied in the field of photocatalysts, can solve the problems that the excited state is difficult to be quenched by the catalyst, the molar extinction coefficient is low, and the stability is not good, so as to achieve excellent photochemical performance, high hydrogen output efficiency and long life. long effect

Active Publication Date: 2019-09-20
扬州万润光电科技股份有限公司
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Problems solved by technology

[0003] In the prior art, more commonly used photosensitizers are ruthenium photosensitizers, such as [Ru(dmphen)3](PF6)2, wherein dmphen is 4,7-dimethyl-1,10-phenanthroline, but its There are disadvantages such as low hydrogen evolution efficiency, poor stability, difficulty in quenching the excited state by the catalyst, and low molar extinction coefficient. In the existing system, the TON value of photoinduced hydrogen evolution is only 92 (TON represents the catalytic activity of the photosensitizer, The higher the value, the better the catalytic activity of the photosensitizer)

Method used

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  • Iridium(iii) complexes based on 2-(4-(dimidylboron)phenyl)pyridine ligands and their preparation methods and applications
  • Iridium(iii) complexes based on 2-(4-(dimidylboron)phenyl)pyridine ligands and their preparation methods and applications
  • Iridium(iii) complexes based on 2-(4-(dimidylboron)phenyl)pyridine ligands and their preparation methods and applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of iridium (III) complex intermediate: 853 mg of ligand 2-(4-(dimethylboron) phenyl) pyridine and 223 mg of iridium chloride hydrate were added to 60 mL of aqueous solution of 2-ethoxyethanol (2- Ethoxyethanol:water=3:1), in N 2 Reflux at 140°C for 24h in the atmosphere. The reaction was stopped, cooled, filtered, washed with 10 mL of water, 10 mL of ethanol, and 10 mL of acetone, and dried to obtain an orange-red powder.

[0030] Mix 418mg of iridium(III) complex intermediate with bipyridyl[3,2-a:2',3'-c]phenazine (2.5eq), anhydrous sodium carbonate (10eq) and add 40mL of methanol and dichloromethane Solution (CH 3 OH:CH 2 Cl 2 =1:1), in N 2 Reflux at 80°C for 24 hours in the atmosphere; then add ammonium hexafluorophosphate (10eq) into the above reaction solution, and continue to reflux for about 3 hours. Dichloromethane and ethanol are used as eluents for chromatographic separation, and the iridium (III) complex is obtained through a recrystallizati...

Embodiment 2

[0033] The preparation of the iridium (III) complex intermediate is the same as in Example 1.

[0034] Add 300 mg of the intermediate of the Ir(III) complex with bipyridyl[3,2-f:2',3'-h]quinoxaline (2.5eq), anhydrous sodium carbonate (10eq) into 40mL of methanol and dichloro Methane mixed solution (CH 3 OH:CH 2 Cl 2 =1:1), in N 2 Reflux at 80°C for 24 hours in the atmosphere; then add ammonium hexafluorophosphate (10eq) into the above reaction solution, and continue to reflux for about 3 hours. Dichloromethane and ethanol are used as eluents for chromatographic separation, and the iridium (III) complex is obtained through a recrystallization process. Yield 250 mg (62%).

[0035] The iridium (III) complex is carried out nuclear magnetic resonance (H spectrogram sees figure 2 ), measured: 1 H NMR (300MHz, CD 3 CN)δ9.65(dd, J=8.3,1.3Hz,2H),9.23(s,2H),8.45(dt,J=12.9,6.5Hz,2H),8.00(dd,J=8.3,5.1Hz, 2H), 7.82(dd, J=13.8, 7.8Hz, 4H), 7.55–7.44(m, 2H), 7.32(d, J=5.4Hz, 2H), 7.1...

Embodiment 3

[0037] The preparation of the iridium (III) complex intermediate is the same as in Example 1.

[0038] Add 410 mg of the intermediate of the iridium (III) complex, 1,10-phenanthroline (2.5 eq) and anhydrous sodium carbonate (10 eq) into a mixed solution of 40 mL of methanol and dichloromethane (CH 3 OH:CH 2 Cl 2 =1:1), in N 2 Reflux at 80°C for 24 hours in the atmosphere; then add ammonium hexafluorophosphate (10eq) into the above reaction solution, and continue to reflux for about 3 hours. Dichloromethane and ethanol are used as eluents for chromatographic separation, and the iridium (III) complex is obtained through a recrystallization process. Yield 380 mg (71%).

[0039] The iridium (III) complex is carried out nuclear magnetic resonance (H spectrogram sees image 3 ), measured: 1 H NMR (300MHz, CD 3 CN)δ8.69(dd,J=8.3,1.3Hz,2H),8.35(dd,J=5.0,1.3Hz,2H),8.24(s,2H),7.91–7.73(m,6H),7.54– 7.43(m,2H),7.21(d,J=5.2Hz,2H),7.10(dd,J=7.8,1.0Hz,2H),6.75(s,8H),6.61–6.49(m,2H),6...

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Abstract

The invention relates to an Iridium(III) coordination complex based on a 2-(4-(dimesitylboryl)benzyl)pyridine ligand, the general chemical formula of the Iridium(III) coordination complex is [Ir(p-B-ppy)2(N^N)](PF6), wherein the p-B-ppy is 2-(4-(dimesitylboryl)benzyl)pyridine, the N^N is bipyridyl[3,2-a:2',3'-c]phenazine or bipyridyl[3,2-f:2',3'-h]quinoxaline or 1,10-phenanthroline. The preparation method includes the following steps that an intermediate of the Iridium(III) coordination complex is added into the mixed solution of methanol and dichloromethane, reflux is performed at the temperature of 80 DEG C under nitrogen for 20-30 hours, then ammonium hexafluorophosphate is added, reflux continues to be performed, and after the reaction, the product is obtained by purification. The Iridium(III) coordination complex has an excellent photochemical property, a good luminous effect and long service time, can be used for preparing hydrogen by photocatalytic water splitting, and the efficiency of hydrogen discharging is high.

Description

technical field [0001] The invention relates to an iridium (III) complex based on 2-(4-(dimethylboron)phenyl)pyridine ligand and belongs to the technical field of photocatalysts. Background technique [0002] The consumption of fossil energy not only causes energy shortage, but also brings severe environmental problems. The development of environmentally friendly, low-cost, and abundant renewable and clean energy is a huge challenge for social development. Using the abundant solar energy in nature to artificially simulate photosynthesis is the goal that human beings have been striving for. The three-component photo-induced hydrogen evolution system based on photosensitizer, catalyst and sacrificial agent is a research hotspot of scientists. An ideal photosensitizer should have good visible light absorption, moderate redox potential, long-lived excited state, and be recyclable. [0003] In the prior art, more commonly used photosensitizers are ruthenium photosensitizers, s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F15/00B01J31/22C01B3/04
CPCB01J31/183B01J35/004B01J2531/827C01B3/042C07F15/0033Y02E60/36
Inventor 杨凌霞于振涛祝梅邹志刚
Owner 扬州万润光电科技股份有限公司
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