Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 663-668.DOI: 10.6023/cjoc201910022 Previous Articles     Next Articles


刘旭波, 林佳乐, 王辉, 张丹维, 黎占亭   

  1. 复旦大学化学系 上海 200438
  • 收稿日期:2019-10-17 修回日期:2019-11-07 发布日期:2020-04-02
  • 通讯作者: 张丹维, 黎占亭;
  • 基金资助:

Water-Solubilization of Acyclic Cucurbiturils for Arenes and Aromatic Aldehydes and the Promotion for the Generation of Two Hydrazine-Based Macrocycles

Liu Xu-Bo, Lin Jia-Le, Wang Hui, Zhang Dan-Wei, Li Zhan-Ting   

  1. Department of Chemistry, Fudan University, Shanghai 200438
  • Received:2019-10-17 Revised:2019-11-07 Published:2020-04-02
  • Supported by:
    Project supported by the National Natural Science Foundation of China (Nos. 21890732, 21921003).

The promotion of two sulfate or carboxylate-bearing acyclic cucurbiturils for the water-solubility of arenes and aromatic aldehydes is described. 1H NMR experiments reveals that sulfate-bearing acyclic cucurbituril (acCB-1) signficantly improves the water-solubility of a number of arenes and aldehydes. For 4,4'-dimethylbiphenyl and biphenyl-4,4'-dicarbaldehyde, the solubility can be improved to 8.9 and 11.2 mmol/L, respectively. 19F NMR experiments demonstrate that carboxylate-bearing acyclic cucurbituril can increase the water-solubilities of pentafluorotoluene and hexafluorobenzene to 5.6 and 3.0 mmol/L, respectively. It is also found that the water-solubilization of acCB-1 for aromatic aldehydes can promote their reaction with acylhydrazines to form hydrozone derivatives. By making use of this promotion, two hydrazone-based macrocycles can be formed from the coupling reactions of two aromatic dialdehdes and one diacylhydrazine in water.

Key words: acyclic cucurbituril, water-solubilization, encapsulation, arene, aromatic aldehyde, hydrazine, macrocycle