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

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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

魏小康, 谷静池, 刘兴丽, 黄超, 朱必学   

  1. 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 出版日期:2018-12-25 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   

  1. Key Laboratory of Macrocyclic and Supramolecular Chemistry, Guizhou University, Guiyang 550025
  • Received:2018-05-03 Revised:2018-07-09 Online:2018-12-25 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)

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 HP2O73- 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 HP2O73- 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 (△rHm, △rSm and △rGm) of the coordination reaction were obtained. The results show that the macrocycle L binds H2PO4- with a 1:1 binding stoichiometry, and binds HP2O73- to form the structure of sandwich-type with a bonding ratio of 2:1.

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