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Two-electron transfer stabilized by excited-state aromatization

Author

Listed:
  • Jinseok Kim

    (Yonsei University)

  • Juwon Oh

    (Yonsei University)

  • Seongchul Park

    (Pusan National University)

  • Jose L. Zafra

    (University of Málaga, Andalucia-Tech, Campus de Teatinos s/n)

  • Justin R. DeFrancisco

    (Johns Hopkins University)

  • David Casanova

    (Donostia, International Physics Center (DIPC) & IKERBASQUE - Basque Foundation for Science)

  • Manho Lim

    (Pusan National University)

  • John D. Tovar

    (Johns Hopkins University)

  • Juan Casado

    (University of Málaga, Andalucia-Tech, Campus de Teatinos s/n)

  • Dongho Kim

    (Yonsei University)

Abstract

The scientific significance of excited-state aromaticity concerns with the elucidation of processes and properties in the excited states. Here, we focus on TMTQ, an oligomer composed of a central 1,6-methano[10]annulene and 5-dicyanomethyl-thiophene peripheries (acceptor-donor-acceptor system), and investigate a two-electron transfer process dominantly stabilized by an aromatization in the low-energy lying excited state. Our spectroscopic measurements quantitatively observe the shift of two π-electrons between donor and acceptors. It is revealed that this two-electron transfer process accompanies the excited-state aromatization, producing a Baird aromatic 8π core annulene in TMTQ. Biradical character on each terminal dicyanomethylene group of TMTQ allows a pseudo triplet-like configuration on the 8π core annulene with multiexcitonic nature, which stabilizes the energetically unfavorable two-charge separated state by the formation of Baird aromatic core annulene. This finding provides a comprehensive understanding of the role of excited-state aromaticity and insight to designing functional photoactive materials.

Suggested Citation

  • Jinseok Kim & Juwon Oh & Seongchul Park & Jose L. Zafra & Justin R. DeFrancisco & David Casanova & Manho Lim & John D. Tovar & Juan Casado & Dongho Kim, 2019. "Two-electron transfer stabilized by excited-state aromatization," Nature Communications, Nature, vol. 10(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-12986-w
    DOI: 10.1038/s41467-019-12986-w
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