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Expanded Rosarin: A Versatile Fullerene (C60) Receptor.

Xian-Sheng Ke1, Taeyeon Kim2, James T Brewster1

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

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|March 21, 2017
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Summary
This summary is machine-generated.

This study details a novel bowl-shaped expanded rosarian (P3P6) capable of forming well-defined complexes with C60 in both solid and solution states. This unfunctionalized porphyrinoid represents a significant advancement in supramolecular chemistry.

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Area of Science:

  • Supramolecular Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Porphyrinoids are versatile macrocycles with applications in catalysis, sensing, and medicine.
  • The development of novel porphyrinoid architectures with specific conformations is crucial for tailored host-guest chemistry.
  • Fullerenes (C60) are unique carbon allotropes with significant electronic and photophysical properties.

Purpose of the Study:

  • To synthesize and characterize a novel bowl-shaped expanded rosarian (P3P6).
  • To investigate the complexation behavior of P3P6 with C60 in both solid and solution states.
  • To explore the potential of unfunctionalized porphyrinoids in forming well-defined supramolecular assemblies.

Main Methods:

  • One-pot synthesis involving condensation of a bispyrrole pyridine precursor with benzaldehyde, followed by oxidation.
  • Single crystal X-ray diffraction for solid-state structural analysis.
  • Density Functional Theory (DFT) calculations for binding energy analysis.
  • Solution-state characterization using 1H NMR, UV-vis, and femtosecond transient absorption spectroscopy.

Main Results:

  • A bowl-like conformation of the expanded rosarian (P3P6) was confirmed with specific dimensions (diameter ~13.5 Å, depth ~6.3 Å).
  • P3P6 forms both 1:1 and 2:1 complexes with C60 in the solid state, with DFT indicating similar binding energies.
  • In solution, a 1:1 binding stoichiometry of P3P6:C60 was observed in 1,2-dichlorobenzene-d4.
  • Spectroscopic studies confirmed solution-phase interactions between the rosarian and C60.

Conclusions:

  • An unfunctionalized expanded rosarian (P3P6) with a distinct bowl-like structure has been successfully synthesized.
  • This rosarian demonstrates the ability to form well-defined complexes with C60 in both solid and solution phases.
  • This work represents the first report of an unfunctionalized porphyrinoid forming stable complexes with C60, opening new avenues for supramolecular chemistry and materials science.