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Dynamic Interconversion between Boroxine Cages Based on Pyridine Ligation.

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Large covalent organic cages can be dynamically interconverted using simple heating or acid/base treatments. This discovery offers new pathways for designing dynamic molecular architectures and controlling cage assembly.

Keywords:
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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Covalent organic cages (COCs) are discrete molecular entities with tunable properties.
  • Dynamic control over the assembly and disassembly of COCs is crucial for their applications.
  • Understanding the thermodynamic and kinetic factors governing COC interconversion is essential.

Purpose of the Study:

  • To investigate the dynamic interconversion of boroxine cages.
  • To explore the influence of external stimuli like heat and acid/base on cage structure.
  • To elucidate the thermodynamic driving forces behind cage assembly and disassembly.

Main Methods:

  • Synthesis of boroxine cages (12-mer and 15-mer).
  • Treatment with pyridine to induce cage conversion.
  • Acid and thermal treatments to reverse the conversion.
  • Spectroscopic analysis to characterize cage structures and transformations.

Main Results:

  • Dynamic interconversion between different-sized boroxine cages (12-mer, 15-mer, and 9-mer) was achieved.
  • Pyridine treatment converted larger cages into a 9-mer pyridine adduct, altering boron atom geometry.
  • Heating or acid treatment reversed the process, favoring larger cages entropically due to pyridine release.

Conclusions:

  • Simple thermal or acid/base stimuli enable dynamic control over covalent organic cage structures.
  • The interconversion process is driven by entropic factors, specifically the release of guest molecules.
  • This work provides a facile method for designing and manipulating dynamic molecular architectures.