Citation: Yi Xianmei, Deng Yaxin, Huang Chao, Zhu Bixue. Syntheses and Structures of Macrocycles Containing 2, 6-Diamidopyridine Unit and their Complex Properties for Tetrahedral Anions[J]. Chemistry, ;2020, 83(9): 821-827. shu

Syntheses and Structures of Macrocycles Containing 2, 6-Diamidopyridine Unit and their Complex Properties for Tetrahedral Anions

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

Corresponding author: Zhu Bixue, bxzhu@gzu.edu.cn
Received Date: 1 March 2020
Accepted Date: 27 May 2020

Figures(6)

[1+1] Schiff base macrocycle L¹ was synthesized from the reaction of precursors N, N'-bis(3-aminophenyl)-pyridine-2, 6-dicarboxamide (1) with 5, 5'-methylene-bis-salicylaldehyde (2), and furthermore the macrocycle L¹ was reduced to the corresponding saturated macrocycle L². The two macrocycles were characterized by¹H NMR, FABMS spectroscopies and elemental analysis, and their crystal structures were determined by X-ray diffraction analysis. The two macrocycles exhibited non-planar structures, and L² showed a more flexible twisted conformation. The complexation of macrocycles with a series of anions was investigated by UV-Vis spectrometric titration technology. The results showed that L¹ had obvious selective recognition ability for tetrahedral anions H₂PO₄^-, HP₂O₇^3-, and H₂P₂O₇^2-, respectively. Properties of the [1+1] Schiff base macrocycle L¹ hydrogen-bonding interactions with these tetrahedral anions were investigated using UV-Vis and¹H NMR titration, respectively. The stoichiometric ratio and binding constant (K) of the interaction were obtained. The results demonstrated that L¹ binded the three anions with a 1:1 binding stoichiometry, and the bonding constants (K_a) increased in the order of H₂PO₄^-, HP₂O₇^3-, H₂P₂O₇^2-.
- Schiff base macrocycle,
- Crystal structures,
- Tetrahedral anion,
- Recognition
1. [1]
  Molina P, Zapata F, Caballero A. Chem. Rev., 2017, 117(15): 9907~9972.
2. [2]
  He Q, Kelliher M, Bähring S, et al. J. Am. Chem. Soc., 2017, 139(21): 7140~7143.
3. [3]
  Zhou H J, Zhao Y S, Gao G, et al. J. Am. Chem. Soc., 2013, 135(40): 14908~14911.
4. [4]
  Chandra B, Mahanta S P, Pati N N. Org. Lett., 2013, 15(2): 306~309.
5. [5]
  Ghite W N, Lovett H G, Beer P D. RSC Adv., 2014, 4: 12133~12147.
6. [6]
  Izawa H, Nishino S, Sumita M. Chem. Commun., 2015, 51(41): 8596~8599.
7. [7]
  Sessler J L, Katayev E, Pantos G D et al. J. Am. Chem. Soc., 2005, 127(32): 11442~11446.
8. [8]
9. [9]
  Ravikumar I, Ghosh P. Chem. Soc. Rev., 2012, 41(8): 3077~3098.
10. [10]
  Dey S K, Das G. Dalton Transac., 2012, 41(29): 8960~8972.
11. [11]
12. [12]
13. [13]
  Chen H Y, Huang C, Ding Y Z, et al. Chem. Sci., 2019, 10: 490~496.
14. [14]
  Chen H Y, Huang C, Deng Y X, et al. ACS Nano., 2019, 13: 2840~2848.
15. [15]
16. [16]
  Marvel C S, Tark N. J. Am. Chem. Soc., 1957, 79(22): 6000~6002.
17. [17]
  Sheldrick G M. SHELX-97, University of Göttingen, Germany, 1997.
18. [18]
  zkar S, Ülkü D, Yildirim L T, et al. J. Mol. Struct., 2004, 688(1/3): 207~211.
19. [19]
  Thordarson P. Chem. Soc. Rev., 2011, 40(3): 1305~1323.
1. [1]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
2. [2]
  Changqing MIAO , Fengjiao CHEN , Wenyu LI , Shujie WEI , Yuqing YAO , Keyi WANG , Ni WANG , Xiaoyan XIN , Ming FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192
3. [3]
  Longfei MA , Fang SI , Congjie PAN , Xinhua WANG . Synthesis and crystal structure of extended tetrathiafulvalene derivatives and cupric bromide charge transfer complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(6): 1229-1236. doi: 10.11862/CJIC.20250355
4. [4]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
5. [5]
  Yan Liu , Yuexiang Zhu , Luhua Lai . Introduction to Blended and Small-Class Teaching in Structural Chemistry: Exploring the Structure and Properties of Crystals. University Chemistry, 2024, 39(3): 1-4. doi: 10.3866/PKU.DXHX202306084
6. [6]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188
7. [7]
  Weina Wang , Fengyi Liu , Wenliang Wang . “Extracting Commonality, Delving into Typicals, Deriving Individuality”: Constructing a Knowledge Graph of Crystal Structures. University Chemistry, 2024, 39(3): 36-42. doi: 10.3866/PKU.DXHX202308029
8. [8]
  Junqiao Zhuo , Xinchen Huang , Qi Wang . Symbol Representation of the Packing-Filling Model of the Crystal Structure and Its Application. University Chemistry, 2024, 39(3): 70-77. doi: 10.3866/PKU.DXHX202311100
9. [9]
  Xiaotong LU , Pan ZHANG , Zijie ZHAO , Lei HUANG , Hongwei ZUO , Lili LIANG . Antitumor and antibacterial activities of pyridyl Schiff base indium and dysprosium complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1523-1532. doi: 10.11862/CJIC.20250073
10. [10]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009
11. [11]
  Wenyan Dan , Weijie Li , Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060
12. [12]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
13. [13]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402
14. [14]
  Xiaoqi LAN , Wei LI , Long JING , Mengyu SU , Xiaoling LUO , Zheng LIU , Qun TANG . Synthesis, crystal structure, and spectral properties of transition-metal-organic frameworks based on thiophene carboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 309-316. doi: 10.11862/CJIC.20250212
15. [15]
  Ruiying WANG , Hui WANG , Fenglan CHAI , Zhinan ZUO , Benlai WU . Three-dimensional homochiral Eu(Ⅲ) coordination polymer and its amino acid configuration recognition. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 877-884. doi: 10.11862/CJIC.20250052
16. [16]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
17. [17]
  Yuyao Wang , Zhitao Cao , Zeyu Du , Xinxin Cao , Shuquan Liang . Research Progress of Iron-based Polyanionic Cathode Materials for Sodium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100035-0. doi: 10.3866/PKU.WHXB202406014
18. [18]
  Linjie ZHU , Xufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207
19. [19]
  Wenjuan SHI , Yuke LU , Xiuyuan LI , Lei HOU , Yaoyu WANG . Mg(Ⅱ) metal-organic frameworks based on biphenyltetracarboxylic acid: Synthesis and CO₂ adsorption and catalytic conversion performance. Chinese Journal of Inorganic Chemistry, 2025, 41(12): 2455-2463. doi: 10.11862/CJIC.20250220
20. [20]
  Junyang FENG , Xiaoli HAN , Yongjie SONG , Gang LI . Proton conduction and fluorescence properties of an ionic hydrogen-bonded organic framework constructed from dibromophthalic acid. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 693-702. doi: 10.11862/CJIC.20250350

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(1969)
HTML views(353)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142