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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Corner units are crucial for synthesizing cyclo-para-phenylenes with strained curved π-systems.
  • Previous corner units had directing angles ≤90°, limiting macrocyclization to six units.

Purpose of the Study:

  • To introduce an obtuse-angled corner unit for synthesizing larger cyclo-para-phenylene congeners.
  • To explore the synthesis of novel macrocyclic structures with enhanced π-systems.

Main Methods:

  • Design and synthesis of an obtuse-angled corner unit (126° directing angle) incorporating oxanorbornadiene.
  • Macrocyclization reactions to form larger cyclo-para-phenylene structures.
  • Reductive aromatization to complete the synthesis of anthracenylene-containing congeners.
  • Experimental and theoretical methods for structural characterization.

Main Results:

  • Successfully synthesized cyclo-para-phenylene congeners using the obtuse-angled corner unit.
  • Achieved macrocyclization of up to seven units, demonstrating the utility of the new corner unit.
  • Obtained structures with multiple anthracenylene panels.
  • Structural studies revealed a fluctuating, non-belt-like shape.

Conclusions:

  • The obtuse-angled corner unit significantly advances the synthesis of strained cyclo-para-phenylenes.
  • Larger and more complex macrocyclic structures with curved π-systems are now accessible.
  • The developed method opens new avenues for designing materials with unique electronic and optical properties.