Ligand molecular compound with diversified steric configuration and Pi electron density and application thereof

A technology of molecular compounds and ligand molecules, applied in organic chemistry, chemical instruments and methods, nanotechnology for materials and surface science, etc.

Active Publication Date: 2018-02-23
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After searching, through a certain reaction method, the ligand molecular compound ferrocene amide compound with a variety of molecular spatial configurations is syn

Method used

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  • Ligand molecular compound with diversified steric configuration and Pi electron density and application thereof
  • Ligand molecular compound with diversified steric configuration and Pi electron density and application thereof
  • Ligand molecular compound with diversified steric configuration and Pi electron density and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Synthesis of Compound Ligand1

[0051] with R 1 =1,4-disubstituted cyclohexyl, R 2 =Phenyl, synthesize the ligand compound Ligand1.

[0052] The reaction pathway is as follows:

[0053]

[0054] Under ice-cooling, mix 11.5g (0.05mol) of ferrocenecarboxylic acid with 100mL of dichloromethane (DCM), and stir evenly. Under strong stirring, 7.0g (0.06mol) N-hydroxysuccinimide (NHS), 11.5g (0.06mol) 1-(3-dimethylaminopropyl)- 3-Ethylcarbodiimide hydrochloride (EDC·HCl). Under ice bath, react for 4-6 hours, the solution gradually becomes clear, and monitor the reaction by TLC. After the reaction was finished, it was suction filtered to obtain a dichloromethane solution of the intermediate (1), which was then used for the next step of reaction.

[0055] Under an ice bath, 8.5 g (0.075 mol) of triethylenediamine was mixed with 50 mL of dichloromethane (DCM) to dissolve, and stirred evenly. Add 24.6mL of 1,4-cyclohexanediamine until the reaction system is uniform and s...

Embodiment 2

[0060] Synthesis of Compound Ligand2

[0061] The preparation method of compound Ligand2 is similar to the preparation of compound Ligand1 in Example 1, the difference is that the 24.6mL 1,4-cyclohexanediamine used in Example 1 is replaced by 27.5mL1,6-hexanediamine, and the compound Ligand2 It is a light yellow powder with a yield of 45.7%;

[0062] 1 H NMR (500MHz, DMSO-d 6 )δ(ppm)=8.45(s,1H), 8.03(m,2H), 7.96~7.80(m,4H), 6.83~6.74(m,3H), 4.53(m,1H), 3.83(s,6H ), 2.6~2.52(m,5H), 3.21~2.83(m,6H), 2.13~1.25(m,14H), C 31 h 42 N 3 o 5 S 2 , ESI-MS: m / z 732.3 (M+1) + .

Embodiment 3

[0064] Synthesis of Compound Ligand3

[0065] The preparation method of compound Ligand3 is similar to the preparation of compound Ligand1 in Example 1, the difference is that the 0.50mL benzaldehyde used in Example 1 is replaced by 0.64mL 4-N,N-dimethylaminobenzaldehyde, compound Ligand3 It is a light yellow powder with a yield of 37.8%;

[0066] 1 H NMR (500MHz, DMSO-d 6 )δ (ppm) = 8.03 (m, 4H), 6.83 ~ 6.74 (m, 3H), 4.53 (m, 1H), 3.83 (s, 6H), 2.6 ~ 2.52 (m, 5H), 3.21 ~ 2.83 (m ,6H), 2.38~1.25(m,24H), C 31 h 49 N 3 o 5 S 2 , ESI-MS: m / z773.3 (M+1) + .

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Abstract

The invention discloses a ligand molecular compound with diversified steric configuration and Pi electron density. The compound is a ferrocenyl amido compound, and is prepared by a special three-stepreaction according to the certain sequence through changing the structure of the different reaction raw materials. The invention further discloses an application of the compound for synthesizing goldnanoparticles with large particle size. Proved by an experiment, the ligand molecular compound is used for synthesizing the gold nanoparticles with the large particle size through a one-step reaction.Compared with a conventional method of more than ten reaction steps, the obvious improvement and optimization are realized. In order to further research the action between nano materials with the different surface properties and a biological system, a model and a method are provided for the ligand molecular compound. The ligand molecular compound has the important reference significance to research the relation between the material surface properties and the biological effect and the relation formed with multiple diseases.

Description

technical field [0001] The present invention relates to a ligand molecule compound ferrocene amide compound with diverse spatial configuration and π-electron density and a synthesis method thereof, and the application of the ligand compound to realize the simple preparation of large-diameter gold nanoparticles; It belongs to the technical field of functional modification of small molecule compounds. Background technique [0002] As an emerging material, nanomaterials are widely used in sporting goods, food, cosmetics, clothing, dyes, etc., in biomedical fields such as drug carriers, cancer treatment, antibacterial materials, tissue engineering, medical diagnosis, and biosensing. It has broad application prospects. On the other hand, the size of nanomaterials has a major impact on their biological effects, and the synthesis methods of nanomaterials with large particle sizes are often complex and cumbersome with lengthy steps. In the synthesis process of nanomaterials, the s...

Claims

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Application Information

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IPC IPC(8): C07F17/02B22F1/00B22F9/24B82Y30/00B82Y40/00
CPCB82Y30/00B82Y40/00C07F17/02B22F9/24B22F1/054
Inventor 闫兵张聪聪王深清江翠娟翟淑梅张秋
Owner SHANDONG UNIV
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