Citation: Liu Xingli, Tang Zhenghe, Chen Dongmei, Zhang Wenlong, Chen Huaiyu, Zhu Chun, Zhu Bixue. Synthesis of 2, 6-Diamidopyridinedipyrromethane Macrocycles and Their Binding Properties for AcO^-[J]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 2911-2918. doi: 10.6023/cjoc201705016 shu

Synthesis of 2, 6-Diamidopyridinedipyrromethane Macrocycles and Their Binding Properties for AcO^-

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

Corresponding author: Zhu Bixue, bxzhu@gzu.edu.cn
Received Date: 9 May 2017
Revised Date: 11 July 2017
Available Online: 30 November 2017
Fund Project: the Graduate Student Innovative Funding of Guizhou University 2017004the “Chun-Hui” Fund of Ministry of Education Z2012054the “Chun-Hui” Fund of Ministry of Education Z2016009the National Natural Science Foundation of China 21663008Project supported by the National Natural Science Foundation of China (No. 21663008), the “Chun-Hui” Fund of Ministry of Education (Nos. Z2012054, Z2016009) and the Graduate Student Innovative Funding of Guizhou University (No. 2017004)

Figures(10)

[1+1] Schiff base macrocycle 3 has been synthesized from the reaction of precursors N, N'-bis(3-aminophenyl)-pyridine-2, 6-dicarboxamide (1) with 5, 5-dimethyl-1, 9-diformyldipyrromethane (2), and furthermore the macrocycle 3 was reduced to the corresponding saturated macrocycle 4. The two macrocycles were characterized by ¹H NMR, FT-IR, FABMS spectroscopies and elemental analysis, and the crystal structure of 4 was determined by X-ray diffraction analysis. Properties of the two macrocycles hydrogen-bonding interactions with AcO^- were investigated using UV-Vis, ¹H NMR, the isothermal titration calorimeter (ITC), as well as density functional theory (DFT) calculations. The stoichiometric ratio, binding constant (K) and the thermodynamic parameters (Δ_rH_m, Δ_rS_m and Δ_rG_m) of binding interactions were obtained. The results demonstrate that the macrocycle 3 binds AcO^- with a 1:1 binding stoichiometry (K_a≈10⁵ L·mol^-1), and the more flexible macrocyclic receptor 4 binds AcO^- with a 1:2 binding stoichiometry (K_a1≈10³ L·mol^-1, K_a2≈10⁵ L·mol^-1).
- 2, 6-diamidopyridine,
- dipyrromethane,
- macrocycle,
- AcO^-,
- hydrogen bond
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沈阳化工大学材料科学与工程学院沈阳 110142

Synthesis of 2, 6-Diamidopyridinedipyrromethane Macrocycles and Their Binding Properties for AcO-

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通讯作者: 陈斌, bchen63@163.com

Synthesis of 2, 6-Diamidopyridinedipyrromethane Macrocycles and Their Binding Properties for AcO^-