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Electro-mechanically switchable hydrocarbons based on [8]annulenes

Author

Listed:
  • Magdalena Tasić

    (Lund University)

  • Jakov Ivković

    (Lund University)

  • Göran Carlström

    (Lund University)

  • Michaela Melcher

    (Lund University)

  • Paolo Bollella

    (Lund University
    University of Bari “A. Moro”)

  • Jesper Bendix

    (University of Copenhagen)

  • Lo Gorton

    (Lund University)

  • Petter Persson

    (Lund University)

  • Jens Uhlig

    (Lund University)

  • Daniel Strand

    (Lund University)

Abstract

Pure hydrocarbons with shape and conjugation properties that can be switched by external stimuli is an intriguing prospect in the design of new responsive materials and single-molecule electronics. Here, we develop an oligomeric [8]annulene-based material that combines a remarkably efficient topological switching upon redox changes with structural simplicity, stability, and straightforward synthesis: 5,12-alkyne linked dibenzo[a,e]cyclooctatetraenes (dbCOTs). Upon reduction, the structures accommodate a reversible reorganization from a pseudo-conjugated tub-shape to a conjugated aromatic system. This switching in oligomeric structures gives rise to multiple defined states that are deconvoluted by electrochemical, NMR, and optical methods. The combination of stable electromechanical responsivity and ability to relay electrons stepwise through an extended (pseudo-conjugated) π-system in partially reduced structures validate alkyne linked dbCOTs as a practical platform for developing new responsive materials and switches based on [8]annulene cores.

Suggested Citation

  • Magdalena Tasić & Jakov Ivković & Göran Carlström & Michaela Melcher & Paolo Bollella & Jesper Bendix & Lo Gorton & Petter Persson & Jens Uhlig & Daniel Strand, 2022. "Electro-mechanically switchable hydrocarbons based on [8]annulenes," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-28384-8
    DOI: 10.1038/s41467-022-28384-8
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