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Relief of excited-state antiaromaticity enables the smallest red emitter

Author

Listed:
  • Heechan Kim

    (Seoul National University)

  • Woojin Park

    (Kyungpook National University)

  • Younghun Kim

    (Seoul National University)

  • Michael Filatov

    (Kyungpook National University)

  • Cheol Ho Choi

    (Kyungpook National University)

  • Dongwhan Lee

    (Seoul National University)

Abstract

It is commonly accepted that a large π-conjugated system is necessary to realize low-energy electronic transitions. Contrary to this prevailing notion, we present a new class of light-emitters utilizing a simple benzene core. Among different isomeric forms of diacetylphenylenediamine (DAPA), o- and p-DAPA are fluorescent, whereas m-DAPA is not. Remarkably, p-DAPA is the lightest (FW = 192) molecule displaying red emission. A systematic modification of the DAPA system allows the construction of a library of emitters covering the entire visible color spectrum. Theoretical analysis shows that their large Stokes shifts originate from the relief of excited-state antiaromaticity, rather than the typically assumed intramolecular charge transfer or proton transfer. A delicate interplay of the excited-state antiaromaticity and hydrogen bonding defines the photophysics of this new class of single benzene fluorophores. The formulated molecular design rules suggest that an extended π-conjugation is no longer a prerequisite for a long-wavelength light emission.

Suggested Citation

  • Heechan Kim & Woojin Park & Younghun Kim & Michael Filatov & Cheol Ho Choi & Dongwhan Lee, 2021. "Relief of excited-state antiaromaticity enables the smallest red emitter," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-25677-2
    DOI: 10.1038/s41467-021-25677-2
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    Cited by:

    1. Kui Yan & Zhubin Hu & Peng Yu & Zuyang He & Ying Chen & Jiajian Chen & Haitao Sun & Shangfeng Wang & Fan Zhang, 2024. "Ultra-photostable small-molecule dyes facilitate near-infrared biophotonics," Nature Communications, Nature, vol. 15(1), pages 1-14, December.

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