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Three-Dimensional Fully Conjugated Carbaporphyrin Cage.

Xian-Sheng Ke1, Taeyeon Kim2, Qing He1

  • 1Department of Chemistry , The University of Texas at Austin , Austin , Texas 78712-1224 , United States.

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Researchers synthesized a novel, large, three-dimensional expanded carbaporphyrin cage. Protonation transforms this nonaromatic molecule into an aromatic system with a significantly larger cavity and tunable electronic properties.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Carbaporphyrins are macrocyclic compounds with unique electronic and structural properties.
  • Developing novel three-dimensional (3D) molecular architectures is crucial for advanced materials.
  • Tuning the aromaticity and cavity size of macrocycles can lead to new functionalities.

Purpose of the Study:

  • To synthesize a fully conjugated 3D expanded carbaporphyrin.
  • To investigate the structural and electronic changes upon protonation.
  • To explore the potential of this new carbaporphyrin for tunable applications.

Main Methods:

  • One-pot synthesis involving [2+4] condensation and oxidation.
  • Single crystal X-ray diffraction for structural analysis.
  • Spectroscopic techniques (UV-vis-NIR, 1H NMR) and computational methods (NICS, ACID) to assess aromaticity and electronic properties.

Main Results:

  • A novel 3D expanded carbaporphyrin (2) with a cage-like structure was successfully synthesized.
  • The as-prepared carbaporphyrin is nonaromatic, featuring a near-zero NICS value.
  • Protonation with trifluoroacetic acid induces global aromaticity, evidenced by a large negative NICS value and increased excited state lifetime.
  • Protonation significantly increases the cavity size to approximately 143 ų.

Conclusions:

  • The largest carbaporphyrin to date with a fully conjugated 3D cage structure has been prepared.
  • Protonation is an effective strategy to tune the aromaticity and cavity dimensions of this carbaporphyrin.
  • This work opens avenues for designing functional macrocyclic materials with controllable electronic and structural characteristics.