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π-Stacking Stopper-Macrocycle Stabilized Dynamically Interlocked [2]Rotaxanes.

Sing-Ming Chan1, Fung-Kit Tang1, Ching-Yau Lam1

  • 1State Key Laboratory of Environmental and Biological Analysis, Department of Chemistry, The Hong Kong Baptist University, Kowloon Tong, Kowloon, Hong Kong, China.

Molecules (Basel, Switzerland)
|August 7, 2021
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel [2]rotaxanes using dynamic imine clipping and π-stacking interactions. Additional π-stacking interactions enhanced the stability and selectivity of these mechanically interlocked molecules.

Keywords:
dynamic combinatorial libraryimine macrocycleintercomponent interactionrotaxane synthesisπ-stacking

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Area of Science:

  • Supramolecular Chemistry
  • Organic Synthesis

Background:

  • Mechanically interlocked molecules (MIMs) possess unique topologies and functionalities.
  • π-stacking interactions are crucial for the self-assembly and stability of MIMs.

Purpose of the Study:

  • To synthesize novel [2]rotaxanes utilizing π-stacking interactions between phenanthroline and anthracene moieties.
  • To investigate the influence of glycol chain length on intercomponent interactions and rotaxane stability.

Main Methods:

  • Dynamic imine clipping reaction for [2]rotaxane synthesis.
  • X-ray crystallography to determine molecular structures and π-stacking interactions.
  • Dynamic combinatorial library (DCL) to assess thermodynamic stability and selectivity.

Main Results:

  • Successful synthesis of anthracene-threaded phenanthroline-based [2]rotaxanes.
  • X-ray structures confirmed π-stacking between anthracene stoppers and macrocyclic aromatic rings.
  • Glycol chain length modulated extra π-stacking interactions, influencing stability.
  • DCL experiments showed up to 84% distribution of the target rotaxane.

Conclusions:

  • π-stacking interactions are key to the formation and stability of these [2]rotaxanes.
  • Additional π-stacking interactions significantly enhance thermodynamic stability and selectivity.
  • This work provides a pathway for designing robust and selective MIMs.