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Triindenoolympicenyl Radical with High Reduction Potential.

Yufei Zhang1, Taoyu Weng2, Jun Xu3

  • 1Institute of Molecular Plus, Department of Chemistry, Tianjin University and Haihe Laboratory of Sustainable Chemical Transformations, 92 Weijin Road, Tianjin 300072, China.

Organic Letters
|March 7, 2026
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Summary
This summary is machine-generated.

Researchers synthesized a stable triindenoolympicenyl radical (TIOR), a type of polycyclic aromatic hydrocarbon (PAH). Indeno annulation significantly increased its reduction potential, offering a new method for tuning PAH redox properties.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Electrochemistry

Background:

  • Spin-1/2 open-shell polycyclic aromatic hydrocarbons (PAHs) display significant redox amphotericity.
  • Achieving high reduction potentials (>-0.5 V) in PAHs is synthetically challenging.
  • Tuning redox properties is crucial for developing advanced organic electronic materials.

Purpose of the Study:

  • To synthesize and characterize a novel stable open-shell polycyclic aromatic hydrocarbon radical.
  • To investigate the effect of indeno annulation on the redox properties of olympicenyl radicals.
  • To establish a new strategy for enhancing the reduction potentials of PAHs.

Main Methods:

  • Synthesis and crystalline-state isolation of triindenoolympicenyl radical (TIOR).
  • Density Functional Theory (DFT) calculations to predict electronic structure and redox potentials.
  • Electrochemical analyses (e.g., cyclic voltammetry) to determine reduction potentials.

Main Results:

  • A stable triindenoolympicenyl radical (TIOR) was successfully synthesized and isolated.
  • Indeno annulation shifted the first reduction potential of TIOR by approximately 1.0 V to more positive values.
  • Compared to the triisopropylsilylethynyl (TIPSE)-substituted olympicenyl radical (OR1), TIOR exhibits significantly enhanced reduction potential.

Conclusions:

  • Indeno annulation is an effective strategy for fine-tuning the redox behavior of open-shell PAHs.
  • The synthesized TIOR demonstrates potential for applications requiring high reduction potentials.
  • This work provides a pathway for designing novel organic materials with tailored electrochemical properties.