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Doubly linked chiral phenanthrene oligomers for homogeneously π-extended helicenes with large effective conjugation length

Author

Listed:
  • Yusuke Nakakuki

    (Kyoto University)

  • Takashi Hirose

    (Kyoto University
    PRESTO, Japan Science and Technology Agency (JST))

  • Hikaru Sotome

    (Osaka University)

  • Min Gao

    (Hokkaido University)

  • Daiki Shimizu

    (Kyoto University)

  • Ruiji Li

    (Kyoto University
    Jining Medical University)

  • Jun-ya Hasegawa

    (Hokkaido University)

  • Hiroshi Miyasaka

    (Osaka University)

  • Kenji Matsuda

    (Kyoto University)

Abstract

Helically twisted conductive nanocarbon materials are applicable to optoelectronic and electromagnetic molecular devices working on the nanometer scale. Herein, we report the synthesis of per-peri-perbenzo[5]- and [9]helicenes in addition to previously reported π-extended [7]helicene. The homogeneously π-extended helicenes can be regarded as helically fused oligo-phenanthrenes. The HOMO−LUMO gap decreased significantly from 2.14 to 1.15 eV with increasing helical length, suggesting the large effective conjugation length (ECL) of the π-extended helical framework. The large ECL of π-extended helicenes is attributed to the large orbital interactions between the phenanthrene subunits at the 9- and 10-positions, which form a polyene-like electronic structure. Based on the experimental results and DFT calculations, the ultrafast decay dynamics on the sub-picosecond timescale were attributed to the low-lying conical intersection.

Suggested Citation

  • Yusuke Nakakuki & Takashi Hirose & Hikaru Sotome & Min Gao & Daiki Shimizu & Ruiji Li & Jun-ya Hasegawa & Hiroshi Miyasaka & Kenji Matsuda, 2022. "Doubly linked chiral phenanthrene oligomers for homogeneously π-extended helicenes with large effective conjugation length," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-29108-8
    DOI: 10.1038/s41467-022-29108-8
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    1. Johannes Zirzlmeier & Stephen Schrettl & Jan C. Brauer & Emmanuel Contal & Laurent Vannay & Éric Brémond & Eike Jahnke & Dirk M. Guldi & Clémence Corminboeuf & Rik R. Tykwinski & Holger Frauenrath, 2020. "Optical gap and fundamental gap of oligoynes and carbyne," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
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