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Highly Twisted Fenestrindane-Based Porous Nanographenes.

Xiao-Qing Sun1, Yuke Li1, Dietmar Kuck2

  • 1Department of Chemistry, The Chinese University of Hong Kong, Shatin, Hong Kong.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 7, 2024
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Summary

Researchers synthesized novel porous nanographenes using fenestrindane building blocks. These twisted structures exhibit unique electronic properties and weak chloride ion binding, paving the way for new materials.

Keywords:
Conjugated macrocyclesFenestranesFenestrindanesNonplanar porous nanographenesPolyaromatic compoundsπ-extension

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Porous nanographenes are advanced carbon materials with tunable properties.
  • Fenestrindane motifs offer unique structural frameworks for novel molecular architectures.
  • Developing new synthetic routes for complex nanographenes is crucial for materials innovation.

Purpose of the Study:

  • To synthesize and characterize novel fenestrindane-based porous nanographenes.
  • To investigate the optical, electronic, and binding properties of these new materials.
  • To explore the structure-property relationships influenced by the twisted conformation.

Main Methods:

  • Multi-step organic synthesis involving Suzuki-Miyaura cross-coupling, Scholl cyclodehydrogenation, and Yamamoto coupling.
  • Characterization using Nuclear Magnetic Resonance (NMR) spectroscopy and mass spectrometry.
  • Analysis of optical and electronic properties via UV/Vis spectroscopy, fluorescence spectroscopy, and cyclic voltammetry.
  • Density Functional Theory (DFT) calculations for structural elucidation.

Main Results:

  • Successful synthesis of two fenestrindane-based porous nanographenes with S4-symmetric conformation.
  • Achieved good yields for precursors and 17-18% yield for the final porous nanographenes.
  • Demonstrated unique optical and electronic properties.
  • Observed surprisingly weak binding affinity with chloride ions (K≈105 M-1) attributed to the twisted structure.

Conclusions:

  • The study presents the first porous nanographenes derived from the [5.5.5.5]fenestrane motif.
  • The highly twisted conformation significantly influences the material's properties, including ion binding.
  • These findings open avenues for designing advanced porous materials with tailored functionalities.