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Aromatic amide metal ligand capable of forming intramolecular hydrogen bonds and its preparation method and application

A kind of technology of metal ligand and aramid, applied in the field of coordination polymer materials

Active Publication Date: 2021-06-25
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Intramolecular hydrogen bonds play a great role in restricting intramolecular rotation, but in the current research, it is hardly seen that the ligand itself in the crystal can form hydrogen bonds to control rotation, so the present invention proposes that intramolecular hydrogen bonds can be formed The ligand can inhibit the intramolecular rotation of the ligand through hydrogen bonds, and can obtain a specific conformation of the ligand when forming a crystal

Method used

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  • Aromatic amide metal ligand capable of forming intramolecular hydrogen bonds and its preparation method and application
  • Aromatic amide metal ligand capable of forming intramolecular hydrogen bonds and its preparation method and application
  • Aromatic amide metal ligand capable of forming intramolecular hydrogen bonds and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Add 1mmol 4,6-dimethoxyisophthalic acid into a round bottom flask, then add 6.9mmol oxalyl chloride, 10mL dichloromethane, 1-2 drops of DMF, react at room temperature for 0.5h, then heat to reflux for 90min, pump Dry the solvent to give 4,6-dimethoxyisophthaloyl chloride. Add 20mL DMA solution of 4,6-dimethoxyisophthaloyl chloride dropwise gradually to 20mL DMA solution containing 8mmol p-aminobenzoic acid and 0.49mL triethylamine, and stir at room temperature for 16h. A large amount of water was added to precipitate the precipitate, and it was suction filtered. The precipitate was washed successively with acetone, a large amount of water and methanol, and dried at room temperature to obtain L1.

[0041] Such as Figure 9 , 1 H NMR (DMSO): δ12.73(s, 2H), 10.28(s, 2H), 8.15(s, 1H), 7.94(d, J=8.7Hz, 4H), 7.87(d, J=8.7Hz, 4H), 6.91(s,1H), 4.08(s,6H).

[0042] Such as Figure 10 , 13 C NMR (DMSO): δ167.40(s), 163.97(s), 161.07(s), 143.39(s), 133.47(s), 130.81(s), 125...

Embodiment 2

[0044]Add 1mmol 4,6-dimethoxyisophthalic acid into a round bottom flask, then add 6.9mmol oxalyl chloride, 10mL dichloromethane, 1-2 drops of DMF, react at room temperature for 0.5h, then heat to reflux for 90min, pump Dry the solvent to give 4,6-dimethoxyisophthaloyl chloride. 20mL DMA solution of 4,6-dimethoxyisophthaloyl chloride was gradually added dropwise to 20mL DMA solution containing 8mmol 4-aminopyridine and 0.49mL triethylamine, and stirred at room temperature for 16h. A large amount of water was added to precipitate the precipitate, and it was suction filtered. The precipitate was washed with copious amounts of water and dried in vacuo to afford L2.

[0045] Such as Figure 11 , 1 H NMR (DMSO): δ10.31(s, 2H), 8.47(d, J=6.2Hz, 4H), 8.10(s, 1H), 7.73(d, J=6.3Hz, 4H), 6.91(s, 1H), 4.07(s, 6H).

[0046] Such as Figure 12 , 13 C NMR (DMSO): δ164.60(s), 161.27(s), 150.82(s), 145.94(s), 133.37(s), 116.39(s), 114.30(s), 97.03(s), 57.28( s).

[0047] In Example 1 ...

Embodiment 3

[0051] Preparation of crystal 1: Cobalt nitrate hexahydrate (0.03mmol, 8.7mg) and L1 (0.03mmol, 13.9mg) were mixed in 4mL DMF, kept at 80°C for 90h, and purple transparent rhombohedral crystals were obtained.

[0052] In addition, mix cobalt chloride hexahydrate (0.03mmol, 7.14mg) and L1 (0.03mmol, 13.9mg) in a mixture of 5mL DMF / EtOH (volume ratio 4:1), keep at 80°C for 90h, and purple can also be obtained Transparent rhombohedral crystals.

[0053] Preparation of Crystal 2: Mix cadmium nitrate tetrahydrate (0.03mmol, 9.2mg) and L1 (0.03mmol, 13.9mg) in a mixed solution of 6mL DMA / MeOH (volume ratio 2:1), keep at 80°C for 90h to obtain Colorless transparent rhombohedral crystals.

[0054] Preparation of Crystal 3: Zinc nitrate hexahydrate (0.03mmol, 6mg), 4,4'-bipyridine (0.039mmol, 6mg) and L1 (0.03mmol, 13.9mg) were mixed in 6mL DMF / H 2 In the mixed solution of O (volume ratio 2:1), keep at 70°C for 90 hours to obtain a mixed solution of crystals and precipitates, wash 5 ...

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Abstract

The invention provides an aramid metal ligand capable of forming intramolecular hydrogen bonds, a preparation method and application thereof, and belongs to the technical field of coordination polymer materials. Aiming at the current problem that some ligands have diverse molecular conformations when forming coordination polymer crystals and are therefore difficult to predict, the present invention proposes ligands that can form intramolecular hydrogen bonds based on the role of intramolecular hydrogen bonds in restricting intramolecular rotation. The inner rotation of the ligand molecule can be suppressed through the hydrogen bond, and the specific conformation of the ligand can be obtained when the crystal is formed, which solves the technical problem.

Description

technical field [0001] The invention belongs to the technical field of coordination polymer materials. Background technique [0002] Coordination polymers have attracted extensive attention from scientists due to their applications in catalysis, gas separation, ion exchange, and magnetism. The crystallization process itself is a dynamic self-assembly process, and it is very meaningful to develop new methods for predicting and controlling the crystal structure of coordination polymers. In crystal engineering, rigid ligands can achieve a good prediction of the structure when synthesizing crystals, assemble into a structure with specific topology and function, and can form a metal-organic framework with permanent pores; It is easy to twist and rotate during the assembly process, resulting in structural diversity, and the pores in the crystal are often dynamically porous that can shrink and expand. [0003] Folded bodies have received great attention due to their applications ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/64C07D213/75C08G83/00C07C231/02
CPCC07C235/64C07D213/75C08G83/008
Inventor 王力彦刘悦邢珮琪裘令瑛李豹
Owner JILIN UNIV