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This study exclusively synthesized a macrocyclic trimer using dynamic Friedel-Crafts alkylation, bypassing typical polymerization competition. The cyclic trimer is the thermodynamically favored product, offering new insights into macrocycle synthesis mechanisms.

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Area of Science:

  • Organic Chemistry
  • Polymer Chemistry
  • Supramolecular Chemistry

Background:

  • Macrocycle synthesis often faces competition from linear polymerization.
  • Controlling cyclization versus polymerization is crucial for efficient macrocycle production.

Purpose of the Study:

  • To achieve exclusive synthesis of a macrocyclic trimer.
  • To investigate the mechanism of dynamic Friedel-Crafts alkylation in macrocycle formation.
  • To understand the competition between cyclization and polymerization.

Main Methods:

  • Exclusive synthesis of a macrocyclic trimer from 1,2,3,4-tetramethoxybenzene and paraformaldehyde.
  • Utilizing dynamic Friedel-Crafts alkylation.
  • Employing Nuclear Magnetic Resonance (NMR) spectroscopy for reaction monitoring.
  • Conducting Density Functional Theory (DFT) studies.

Main Results:

  • The reaction exclusively yielded a macrocyclic trimer, avoiding polymer formation.
  • Dynamic Friedel-Crafts alkylation proceeded via linear oligomeric intermediates that converted to the cyclic trimer.
  • NMR monitoring confirmed the stepwise conversion process.
  • DFT calculations identified the cyclic trimer as the thermodynamically most stable species.

Conclusions:

  • The developed system successfully circumvents the cyclization-polymerization equilibrium.
  • This work provides valuable insights into the mechanistic competition during macrocycle synthesis.
  • The exclusive formation of the macrocyclic trimer highlights a novel synthetic strategy.