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Ir (III)-based chiral metal-organic porous material with splitting function as well as preparation method and application of Ir (III)-based chiral metal-organic porous material

A porous material, chiral technology, applied in organic chemistry methods, preparation of organic compounds, organic racemization, etc., can solve problems such as limiting the resolution effect, and achieve the effect of good application prospects, efficient resolution, and high yield.

Active Publication Date: 2022-03-22
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, there is only one chiral module in the current metal-organic porous materials, which greatly limits its resolution effect

Method used

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  • Ir (III)-based chiral metal-organic porous material with splitting function as well as preparation method and application of Ir (III)-based chiral metal-organic porous material
  • Ir (III)-based chiral metal-organic porous material with splitting function as well as preparation method and application of Ir (III)-based chiral metal-organic porous material
  • Ir (III)-based chiral metal-organic porous material with splitting function as well as preparation method and application of Ir (III)-based chiral metal-organic porous material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of the target compound LP1: the Λ - fac -Ir-CHO (37.0 mg , 0.05 mmol) and 1 S ,2 S -Cyclohexanediamine (11.4 mg, 0.10 mmol) was placed in a 50 mL three-necked flask, to which was added 30 mL of toluene and acetonitrile solvent with a volume ratio of 1:2, stirred to dissolve completely, and then 15 mol% p-toluene was added Sulfonic acid was reacted under argon atmosphere at 110 °C for 12 h. After the reaction solution was cooled to room temperature, it was distilled under reduced pressure to obtain an orange-yellow solid, which was dissolved in dichloromethane and diffused with ether to obtain crystalline LP1, 38.5 mg, yield 90 %. Theoretical value of elemental analysis [C 90 h 78 Ir 2 N 12 ·H 2 O·(C 7h 8 )]: H, 4.87; C, 69.93; N, 9.22. The experimental values ​​are H, 4.81; C, 61.68; N, 9.54. The obtained target material structure is as follows figure 1 As shown, the NMR spectrum is shown as figure 2 As shown, the mass spectrogram is as image...

Embodiment 2

[0045] Synthesis of the target compound LP3: the Λ - fac -Ir-CHO (37.0 mg, 0.05 mmol) and (S)-(-)-diaminopropane (7.4 mg, 0.10 mmol) were placed in a 50 mL three-necked flask, and 35 mL of Toluene and acetonitrile solvent, stir to dissolve completely, then add 15 mol% p-toluenesulfonic acid, react under argon atmosphere at 100 °C for 13.5 h, after the reaction solution is cooled to room temperature, distill under reduced pressure to obtain an orange-yellow solid, which is dissolved in In dichloromethane, diethyl ether was diffused to obtain crystalline LP3, 36.6 mg, with a yield of 92%. The obtained target material LP3 structure was identified by mass spectrometry, HRMS-ESI m / z calcd for C 81 h 67 Ir 2 N 12 [M+H] + 1593.4878 found 1598.4831

Embodiment 3

[0047] Synthesis of the target compound LP4: the Λ - fac -Ir-CHO (37.0 mg, 0.05 mmol) and (1S,2S)-1,2-diphenylethylenediamine (25.4 mg, 0.12mmol) were placed in a 50 mL three-necked flask, and 45 mL volume ratio of Toluene and acetonitrile solvent of 1:2.5, stirred to dissolve completely, then added 15 mol% p-toluenesulfonic acid, reacted under argon atmosphere at 120 ℃ for 10h, after the reaction solution was cooled to room temperature, it was distilled under reduced pressure to obtain an orange-yellow solid, It was dissolved in dichloromethane and diffused with ether to obtain crystalline LP4, 46.5 mg, with a yield of 93%. The structure of the obtained target material LP4 was identified by mass spectrometry, HRMS-ESI m / z calcd for C 114 h 85 Ir 2 N 12 [M+H] + 2007.6298 found 2007.6200.

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Abstract

The invention discloses an Ir (III)-based chiral metal-organic porous material with a resolution function as well as a preparation method and application thereof, and belongs to the technical field of chiral compound resolution. According to the material, chiral Ir (III)-based complexes L1 and L2 are used as construction modules and are respectively subjected to Schiff base reaction with chiral diamines P1 and P2 to generate a chiral metal-organic porous material; the method comprises the following steps: by taking 1, 1 '-co-2-naphthol as a to-be-resolved molecule, adding a solvent, taking the obtained multi-chiral helical compound as a solid resolving agent, and realizing adsorption separation of a corresponding single chiral molecule through solid-liquid stirring. The Ir (III) complex enables the chirality of the target material to be maintained for a long time; the introduction of chiral diamine enriches the chiral information of the pore channel of the target crystalline material, realizes the strict matching with chiral molecules, and realizes the efficient resolution of 1, 1 '-co-2-naphthol (ee is as high as gt, 99%).

Description

technical field [0001] The invention relates to an Ir(III)-based chiral metal-organic porous material capable of resolving 1,1'-bi-2-naphthol, a preparation method and application thereof, and belongs to the technical field of chiral compound resolution. Background technique [0002] Photoactive 1,1'-bi-2-naphthol and its derivatives are widely used in the field of asymmetric catalysis and chiral recognition. How to obtain optically pure products of 1,1'-bi-2-naphthol has become a concern of scientists one of the hotspots. At present, the methods for obtaining optically pure 1,1'-bi-2-naphthol are mainly divided into two categories: 1. Direct synthesis method: adding a chiral catalyst such as (-)-chrysanthemum to the oxidative coupling reaction of naphthalene diol Alkaline yields the product S -1,1'-linked-2-naphthol; two, chiral resolution method: utilize chiral resolution reagents such as (8 S ,9 R )-(-)-N-benzyl cinchonidine chloride, R -Methylbenzylamine, etc., heat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F15/00C07C37/86C07C39/14C07B57/00
CPCC07F15/0033C07C37/685C07C37/86C07B57/00C07B2200/07C07C39/14
Inventor 何成吴金国李学召
Owner DALIAN UNIV OF TECH
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