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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 7: 2236 - 2242

DOI: https://doi.org/10.6023/cjoc202202038

ARTICLES

Gradient Enhancement of Supramolecular Organic Framework for Solubilization of Hydrophobic Molecules by Two Molecular Containers in Water

  • Ze-Kun Wang ,
  • Zi-Yue Xu ,
  • Juan-Juan Li ,
  • Shang-Bo Yu ,
  • Hui Wang ,
  • Dong-Sheng Guo ,
  • Dan-Wei Zhang ,
  • Zhan-Ting Li
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  • aDepartment of Chemistry, Shanghai Key Laboratory of Molecular Catalysis and Innovative Materials, Fudan University, Shanghai 200438
    bCollege of Chemistry, State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071
    cKey Laboratory of Synthetic and Self-Assembly Chemistry for Organic Functional Molecules, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032
* E-mail:

Received date: 2022-02-28

  Revised date: 2022-03-13

  Online published: 2022-03-22

Supported by

National Natural Science Foundation of China(21921003); National Natural Science Foundation of China(21890730); National Natural Science Foundation of China(21890732)

Fold

Abstract

Many functional organic molecules have very low water-solubility, which remarkably limits their practical applications. The inclusion of water-soluble hosts has been demonstrated as an important strategy to increase the water solubility of organic molecules. However, this strategy usually requires high concentration for the hosts to realize efficient solubilization of guest molecules. Herein a new strategy of gradient solubilization by utilizing a water-soluble porous supramolecular polymer to adsorb or enrich molecular containers to increase their efficient concentration in a confined space is reported. For this aim, a cationic water-soluble supramolecular organic framework was used to include an anionic calix[5]arene or an anionic acyclic cucurbituril. In this way, the supramolecular organic framework was revealed to exhibit significant gradient enhancement for the solubilization of the calix[5]arene host for C60, C70, ferrocene, 1,1'-dimethylferrocene and 1,1'-dibromoferrocene, and the solubilization of the acyclic cucurbituril host for paclitaxel, docetaxel and cabazitaxel.

Key words： supramolecular organic framework; host-guest chemistry; calixarene; acyclic cucurbituril; gradient solubilization; fullerene; ferrocene; paclitaxel

Cite this article

Ze-Kun Wang , Zi-Yue Xu , Juan-Juan Li , Shang-Bo Yu , Hui Wang , Dong-Sheng Guo , Dan-Wei Zhang , Zhan-Ting Li . Gradient Enhancement of Supramolecular Organic Framework for Solubilization of Hydrophobic Molecules by Two Molecular Containers in Water[J]. Chinese Journal of Organic Chemistry, 2022 , 42(7) : 2236 -2242 . DOI: 10.6023/cjoc202202038

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