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BINOL-like atropisomeric chiral nanographene.

Shengtao Li1, Ranran Li1, Yi-Kang Zhang1

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Researchers developed a new chiral oxa-nanographene (NG) through dimerization. This novel molecule exhibits stable atropisomerism and functions as an efficient photosensitizer for singlet oxygen generation.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Chiral nanocarbons, particularly polycyclic aromatic hydrocarbons (PAHs) and nanographenes (NGs), are gaining interest.
  • Current chiral nanocarbon designs predominantly rely on helical chirality.

Purpose of the Study:

  • To synthesize and characterize a novel atropisomeric chiral oxa-nanographene (oxa-NG 1).
  • To investigate the photophysical properties and potential applications of this new chiral nanographene.

Main Methods:

  • Selective dimerization of a naphthalene-containing hexa-peri-hexabenzocoronene (HBC)-based PAH (6).
  • Photophysical characterization (UV-vis absorption, fluorescence emission, decay, quantum yield).
  • Single-crystal X-ray diffraction, chiral high-performance liquid chromatography (HPLC), circular dichroism (CD), circularly polarized luminescence (CPL), and density functional theory (DFT) calculations.

Main Results:

  • A novel atropisomeric chiral oxa-NG 1 was synthesized via dimerization of PAH 6.
  • The oxa-NG 1 maintained photophysical properties similar to its monomer due to a perpendicular conformation.
  • Enantiomers were resolved by chiral HPLC, and their CD/CPL spectra showed opposite signals.
  • High racemic barrier (35 kcal mol-1) indicated a rigid structure.
  • The oxa-NG 1 demonstrated efficient singlet oxygen generation under white light.

Conclusions:

  • A new class of atropisomeric chiral nanographenes with potential applications in photochemistry was developed.
  • The perpendicular conformation preserves monomer photophysical properties in the dimer.
  • The synthesized oxa-NG 1 is a promising photosensitizer for singlet oxygen generation.