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A crystalline radical cation derived from Thiele’s hydrocarbon with redox range beyond 1 V

Author

Listed:
  • Ying Kai Loh

    (University of Oxford)

  • Petra Vasko

    (University of Jyväskylä)

  • Caitilín McManus

    (University of Oxford)

  • Andreas Heilmann

    (University of Oxford)

  • William K. Myers

    (University of Oxford)

  • Simon Aldridge

    (University of Oxford)

Abstract

Thiele’s hydrocarbon occupies a central role as an open-shell platform for new organic materials, however little is known about its redox behaviour. While recent synthetic approaches involving symmetrical carbene substitution of the CPh2 termini yield isolable neutral/dicationic analogues, the intervening radical cations are much more difficult to isolate, due to narrow compatible redox ranges (typically 1 V), permitting its isolation in crystalline form. Further single-electron oxidation affords borenium dication 12+, thereby establishing an organoboron redox system fully characterized in all three redox states. We perceive that this strategy can be extended to other transient organic radicals to widen their redox stability window and facilitate their isolation.

Suggested Citation

  • Ying Kai Loh & Petra Vasko & Caitilín McManus & Andreas Heilmann & William K. Myers & Simon Aldridge, 2021. "A crystalline radical cation derived from Thiele’s hydrocarbon with redox range beyond 1 V," Nature Communications, Nature, vol. 12(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-27104-y
    DOI: 10.1038/s41467-021-27104-y
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    Cited by:

    1. Yu-Jiang Lin & Wei-Chun Liu & Yi-Hung Liu & Gene-Hsiang Lee & Su-Ying Chien & Ching-Wen Chiu, 2022. "A linear Di-coordinate boron radical cation," Nature Communications, Nature, vol. 13(1), pages 1-8, December.

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