Synthesis and Spectral Analysis of Metal-organic Macrocyclic Compound for Detection of Glucosamine

WU Hong-mei; GUO Yu; CAO Jian-fang; CHEN Qiang-qiang; ZHANG Zhi-hua

doi:10.3788/fgxb20183908.1163

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Synthesis and Spectral Analysis of Metal-organic Macrocyclic Compound for Detection of Glucosamine

更新时间：2020-08-12

- Synthesis and Spectral Analysis of Metal-organic Macrocyclic Compound for Detection of Glucosamine
- Chinese Journal of Luminescence Vol. 39, Issue 8, Pages: 1163-1169(2018)
- 作者机构：
  
  辽宁工业大学化学与环境工程学院, 辽宁锦州 121001
- 作者简介：
- 基金信息：
  
  Supported by National Natural Science Foundation of China(21601075,21606118);Natur
- DOI：10.3788/fgxb20183908.1163
  CLC： O433.5
- Received：24 January 2018，
  
  Revised：20 May 2018，
  
  Published：05 August 2018
- 稿件说明：
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吴红梅, 郭宇, 曹建芳等. 用于检测氨基葡萄糖的金属-有机大环化合物的合成及光谱分析[J]. 发光学报, 2018,39(8): 1163-1169

WU Hong-mei, GUO Yu, CAO Jian-fang etc. Synthesis and Spectral Analysis of Metal-organic Macrocyclic Compound for Detection of Glucosamine[J]. Chinese Journal of Luminescence, 2018,39(8): 1163-1169
吴红梅, 郭宇, 曹建芳等. 用于检测氨基葡萄糖的金属-有机大环化合物的合成及光谱分析[J]. 发光学报, 2018,39(8): 1163-1169 DOI： 10.3788/fgxb20183908.1163.

WU Hong-mei, GUO Yu, CAO Jian-fang etc. Synthesis and Spectral Analysis of Metal-organic Macrocyclic Compound for Detection of Glucosamine[J]. Chinese Journal of Luminescence, 2018,39(8): 1163-1169 DOI： 10.3788/fgxb20183908.1163.

摘要

以5-氨基异酞酸为初始原料，通过酯化、肼解和席夫碱等反应合成了双三齿配体LD，并通过与锌离子（Zn

）自组装构筑了金属（锌）-有机大环化合物LD-Zn，利用紫外-可见光谱、核磁、电喷雾质谱等表征手段研究了LD-Zn对氨基葡萄糖的识别作用。核磁光谱和电喷雾质谱测试表明，氨基葡萄糖分子能够进入到大环LD-Zn内部，并且LD-Zn以1：1的比例包合了氨基葡萄糖分子。紫外-可见光谱表明，当向LD-Zn中加入氨基葡萄糖后，373 nm处的吸收峰强度增加，269 nm和303 nm处的吸收峰强度降低，平衡常数

达到4.1910

L/mol，最低检测限为5.010

-6

mol/L。通过对比测试发现，LD-Zn只对氨基葡萄糖有紫外光谱响应，而对葡萄糖和三乙胺无任何响应，说明氨基葡萄糖的结构与大环化合物LD-Zn的空腔更匹配，LD-Zn对氨基葡萄糖的识别不是单纯羟基（氢键）或者氨基（碱性）引起的，而是由LD-Zn限域的空腔效应和氨基的氢键协同作用实现了对氨基葡萄糖的识别。

Abstract

Double-tridentate ligand LD was synthesized by 5-aminophthalic acid through esterification

hydrazinolysis and Schiff's base reactions. Then

a novel metal-organic macrocyclic LD-Zn was built by the assembly of LD and zinc ions for the recognition of glucosamine. The detection mechanism of glucosamine with LD-Zn was studied by UV-Vis

H NMR and ESI-MS. The results of

H NMR and ESI-MS indicate that the glucosamine molecules could enter the LD-Zn. Moreover

1:1 stoichiometric host-guest complexation between glucosamine and LD-Zn was formed. UV-Vis spectra show that the intensity of the absorption peak at 373 nm increased significantly after addition of glucosamine into LD-Zn. However

the absorption intensity at 269 nm and 303 nm decreases. The equilibrium constant

reaches 4.1910

L/mol

and the minimum detection limit is 5.010

-6

mol/L. For comparison

the detection tests of glucose and triethylamine with LD-Zn were carried out. The UV-Vis spectra do not show any response when glucose and triethylamine are added to LD-Zn. These results indicate that the structure of glucosamine is more compatible with the cavity of the macrocycle LD-Zn compared to glucose and triethylamine. The recognition of glucosamine by using LD-Zn is not attributed to pure hydroxyl(hydrogen bonding) or amino(alkaline)

it is mainly caused by the joint effect of confined cavity of LD-Zn molecular and hydrogen bonds of amino.

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Keywords

references

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