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Chemists have developed a versatile fjord-stitching method to synthesize zigzag hydrocarbon belts and heteroatom-doped analogs, enabling new molecular architectures with tunable properties.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Cyclacenes, proposed in 1954, are zigzag hydrocarbon belts with potential applications but lacked synthetic methods.
  • Previous attempts to synthesize these belts were limited, leading to decades of stagnation in the field.
  • Heteracalix[n]aromatics, developed in the early 2000s, offered a new class of macrocyclic hosts with tunable conformations.

Purpose of the Study:

  • To develop a synthetic strategy for constructing zigzag-type molecular belts.
  • To explore the synthesis of strained belt[8]arenes and their derivatives.
  • To investigate the creation of heteroatom-doped zigzag belts and their properties.

Main Methods:

  • Utilized cone-conformational resorcin[4]arenes and functionalized phenolic hydroxyl groups.
  • Employed intramolecular Friedel-Crafts alkylation for fjord-stitching to form H8-belt[8]arenes.
  • Applied oxidative aromatization with DDQ and laser irradiation for retro-Diels-Alder reactions to yield belt[8]arene.
  • Extended fjord-stitching to include Friedel-Crafts alkylation/acylation and olefin metathesis for diverse hydrocarbon belts.
  • Incorporated SNAr reactions and transition-metal-mediated coupling for heteroatom-doped belts.
  • Utilized CAr-CAr homocoupling for globally aromatic zigzag belts.

Main Results:

  • Successfully synthesized belt[8]arene, a fully conjugated zigzag hydrocarbon belt, for the first time.
  • Developed a versatile fjord-stitching strategy enabling the synthesis of diverse hydrocarbon belts with varying sizes, shapes, and functional groups.
  • Constructed heteroatom-doped zigzag belts by bridging fjords with oxygen and nitrogen atoms.
  • Synthesized globally aromatic zigzag belts composed of pyrrole and pyridine subunits.
  • Observed unique structural diversity in zigzag belts, leading to cavities ranging from prisms to truncated cones and frustums.
  • Demonstrated intriguing photophysical and electrochemical properties and selective guest complexation in zigzag belts.

Conclusions:

  • The fjord-stitching method is a powerful and versatile strategy for synthesizing a wide array of zigzag-type molecular belts.
  • Zigzag-type belts exhibit unique structural features and tunable properties, making them promising for various applications.
  • This research revitalizes the field of cyclacenes and related molecular belts, paving the way for practical applications.