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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 3: 663 - 668

DOI: https://doi.org/10.6023/cjoc201910022

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
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  • Department of Chemistry, Fudan University, Shanghai 200438

Received date: 2019-10-17

  Revised date: 2019-11-07

  Online published: 2020-04-02

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21890732, 21921003).

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Abstract

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

Cite this article

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

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