Synthesis and Anion Recognition of Macrocycle Containing Isophthalamide Unit

doi:10.6023/cjoc201805012

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (12): 3386-3393.DOI: 10.6023/cjoc201805012 Previous Articles Next Articles

Notes

含间苯二甲酰胺基的大环合成及其对阴离子的识别研究

魏小康, 谷静池, 刘兴丽, 黄超, 朱必学

贵州大学大环及超分子化学重点实验室贵阳 550025

收稿日期:2018-05-03 修回日期:2018-07-09 发布日期:2018-08-14
通讯作者: 朱必学 E-mail:bxzhu@gzu.edu.cn
基金资助:
贵州省科技厅、贵州大学联合项目（No.LH[2017]7256）和教育部春晖计划（No.Z2016009）资助项目.

Synthesis and Anion Recognition of Macrocycle Containing Isophthalamide Unit

Wei Xiaokang, Gu Jingchi, Liu Xingli, Huang Chao, Zhu Bixue

Key Laboratory of Macrocyclic and Supramolecular Chemistry, Guizhou University, Guiyang 550025

Received:2018-05-03 Revised:2018-07-09 Published:2018-08-14
Contact: 10.6023/cjoc201805012 E-mail:bxzhu@gzu.edu.cn
Supported by:
Project supported by the Joint Project of Science and Technology Department of Guizhou Province (No. LH[2017]7256) and the "Chun-Hui" Fund of Ministry of Education (No. Z2016009)

1. Synthesis and Anion Recognition of Macrocycle Containing Isophthalamide Unit.PDF(555KB)

Abstract

A[1+1] Schiff base macrocyclic compound L containing isophthalamide unit and phenol rings has been synthesized from the reaction of precursors N,N'-(6-amino-2-pyridyl)-1,3-dicarboximide with 5,5'-methylene bis-salicylaldehyde by Schiff-base condensation. The macrocycle L was characterized via ¹H NMR, FABMS, and elemental analysis. The crystal structure of L was determined by X-ray diffraction analysis, and it has a folded clamp conformation. In the crystal state of L, individual macrocycles were assembled into columnar structures with 1D channel through intermolecular hydrogen bonding and π-π stacking interactions. The results show that the macrocycle L displays a selective recognition ability for H₂PO₄^- and HP₂O₇^3- anion respectively by the coordination reaction of L with a series of anions using UV-Vis absorption spectra technique. Furthermore, the coordination reaction of L with H₂PO₄^- or HP₂O₇^3- anion was investigated via UV-Vis spectra, ¹H NMR and the isothermal titration calorimeter (ITC) respectively. The stoichiometric ratio, the association constant (K) and the thermodynamic parameters (△_rH_m, △_rS_m and △_rG_m) of the coordination reaction were obtained. The results show that the macrocycle L binds H₂PO₄^- with a 1:1 binding stoichiometry, and binds HP₂O₇^3- to form the structure of sandwich-type with a bonding ratio of 2:1.

Key words: isophthalamide, phenol ring, Schiff-base macrocycle, anion, recognition

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Wei Xiaokang, Gu Jingchi, Liu Xingli, Huang Chao, Zhu Bixue. Synthesis and Anion Recognition of Macrocycle Containing Isophthalamide Unit[J]. Chin. J. Org. Chem., 2018, 38(12): 3386-3393.

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含间苯二甲酰胺基的大环合成及其对阴离子的识别研究

Synthesis and Anion Recognition of Macrocycle Containing Isophthalamide Unit

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