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Stacked antiaromatic porphyrins

Author

Listed:
  • Ryo Nozawa

    (Graduate School of Engineering, Nagoya University)

  • Hiroko Tanaka

    (Graduate School of Engineering, Nagoya University)

  • Won-Young Cha

    (Yonsei University)

  • Yongseok Hong

    (Yonsei University)

  • Ichiro Hisaki

    (Graduate School of Engineering, Osaka University)

  • Soji Shimizu

    (Graduate School of Engineering, Kyushu University)

  • Ji-Young Shin

    (Graduate School of Engineering, Nagoya University)

  • Tim Kowalczyk

    (Advanced Materials Science and Engineering Center, and Institute for Energy Studies, Western Washington University)

  • Stephan Irle

    (Graduate School of Science, Nagoya University)

  • Dongho Kim

    (Yonsei University)

  • Hiroshi Shinokubo

    (Graduate School of Engineering, Nagoya University)

Abstract

Aromaticity is a key concept in organic chemistry. Even though this concept has already been theoretically extrapolated to three dimensions, it usually still remains restricted to planar molecules in organic chemistry textbooks. Stacking of antiaromatic π-systems has been proposed to induce three-dimensional aromaticity as a result of strong frontier orbital interactions. However, experimental evidence to support this prediction still remains elusive so far. Here we report that close stacking of antiaromatic porphyrins diminishes their inherent antiaromaticity in the solid state as well as in solution. The antiaromatic stacking furthermore allows a delocalization of the π-electrons, which enhances the two-photon absorption cross-section values of the antiaromatic porphyrins. This feature enables the dynamic switching of the non-linear optical properties by controlling the arrangement of antiaromatic π-systems on the basis of intermolecular orbital interactions.

Suggested Citation

  • Ryo Nozawa & Hiroko Tanaka & Won-Young Cha & Yongseok Hong & Ichiro Hisaki & Soji Shimizu & Ji-Young Shin & Tim Kowalczyk & Stephan Irle & Dongho Kim & Hiroshi Shinokubo, 2016. "Stacked antiaromatic porphyrins," Nature Communications, Nature, vol. 7(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:7:y:2016:i:1:d:10.1038_ncomms13620
    DOI: 10.1038/ncomms13620
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    Cited by:

    1. Jian Chen & Feixiang Chen & Xueli Wang & Hongjun Zhuang & Mengnan Guo & Luo Wang & Junze Xie & Le Zhang & Hao Liu & Yuhan Shi & Jiajia Zhou & Xinjie Mao & Muyao Lv & Xingwu Jiang & Jinquan Chen & Yany, 2024. "Ultra-fast photoelectron transfer in bimetallic porphyrin optoelectrode for single neuron modulation," Nature Communications, Nature, vol. 15(1), pages 1-12, December.

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