Citation: Liu Xu-Bo, Lin Jia-Le, Wang Hui, Zhang Dan-Wei, Li Zhan-Ting. Water-Solubilization of Acyclic Cucurbiturils for Arenes and Aromatic Aldehydes and the Promotion for the Generation of Two Hydrazine-Based Macrocycles[J]. Chinese Journal of Organic Chemistry, ;2020, 40(3): 663-668. doi: 10.6023/cjoc201910022 shu

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

Department of Chemistry, Fudan University, Shanghai 200438

Corresponding author: Zhang Dan-Wei, zhangdw@fudan.edu.cn Li Zhan-Ting, ztli@fudan.edu.cn
Received Date: 17 October 2019
Revised Date: 7 November 2019
Available Online: 21 November 2019
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21890732, 21921003)the National Natural Science Foundation of China 21890732the National Natural Science Foundation of China 21921003

Figures(4)

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.
- acyclic cucurbituril,
- water-solubilization,
- encapsulation,
- arene,
- aromatic aldehyde,
- hydrazine,
- macrocycle
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