Citation: Wei Xiaokang, Gu Jingchi, Liu Xingli, Huang Chao, Zhu Bixue. Synthesis and Anion Recognition of Macrocycle Containing Isophthalamide Unit[J]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3386-3393. doi: 10.6023/cjoc201805012 shu

Synthesis and Anion Recognition of Macrocycle Containing Isophthalamide Unit

Key Laboratory of Macrocycli3 and Supramolecular Chemistry, Guizhou University, Guiyang 550025

Corresponding author: Zhu Bixue, bxzhu@gzu.edu.cn
Received Date: 3 May 2018
Revised Date: 9 July 2018
Available Online: 14 December 2018
Fund Project: the Joint Project of Science and Technology Department of Guizhou Province LH[2017]7256Project 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)the "Chun-Hui" Fund of Ministry of Education Z2016009

Figures(8)

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.
- isophthalamide,
- phenol ring,
- Schiff-base macrocycle,
- anion,
- recognition
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