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Flexibility Coexists with Shape-Persistence in Cyanostar Macrocycles.

Yun Liu1, Abhishek Singharoy2, Christopher G Mayne2

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Flexible yet shape-persistent macrocycles, like cyanostar, challenge traditional definitions. This study shows flexible molecules can be shape-persistent if their various conformations maintain similar shapes, expanding the scope of macrocycle design.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Computational Chemistry

Background:

  • Shape-persistent macrocycles are traditionally defined by rigidity and low conformational flexibility.
  • This study re-evaluates these definitions in the context of flexible yet shape-persistent molecules.

Purpose of the Study:

  • To investigate the relationship between macrocycle flexibility, shape persistence, and function.
  • To examine the conformational behavior of the flexible, star-shaped macrocycle, cyanostar.
  • To expand the definition of shape persistence to include flexible macrocycles.

Main Methods:

  • Molecular dynamics (MD) simulations.
  • Density functional theory (DFT) calculations.
  • Nuclear Magnetic Resonance (NMR) spectroscopy.

Main Results:

  • Cyanostar exhibits 332 accessible conformers due to rapid interconversion of olefin groups.
  • Despite flexibility, cyanostar maintains 87% shape similarity across its conformers, confirming shape persistence.
  • Guest-induced binding (diglyme) minimally affects conformational space, but complex formation enhances rigidity.

Conclusions:

  • Flexible macrocycles can be considered shape-persistent if their conformers exhibit high shape similarity.
  • This finding broadens the design principles for functional macrocycles in molecular recognition and self-assembly.