Stacked antiaromatic porphyrins

Ryo Nozawa, Hiroko Tanaka, Won Young Cha, Yongseok Hong, Ichiro Hisaki, Soji Shimizu, Ji Young Shin, Tim Kowalczyk, Stephan Irle, Dongho Kim, Hiroshi Shinokubo

研究成果: ジャーナルへの寄稿記事

33 引用 (Scopus)

抄録

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.

元の言語英語
記事番号13620
ジャーナルNature communications
7
DOI
出版物ステータス出版済み - 11 30 2016

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organic chemistry
Organic Chemistry Phenomena
Porphyrins
porphyrins
Organic Chemistry
orbitals
textbooks
Nonlinear Dynamics
Textbooks
Photons
absorption cross sections
Optical properties
interactions
Electrons
solid state
optical properties
Molecules
photons
predictions
molecules

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Biochemistry, Genetics and Molecular Biology(all)
  • Physics and Astronomy(all)

これを引用

Nozawa, R., Tanaka, H., Cha, W. Y., Hong, Y., Hisaki, I., Shimizu, S., ... Shinokubo, H. (2016). Stacked antiaromatic porphyrins. Nature communications, 7, [13620]. https://doi.org/10.1038/ncomms13620

Stacked antiaromatic porphyrins. / Nozawa, Ryo; Tanaka, Hiroko; Cha, Won Young; Hong, Yongseok; Hisaki, Ichiro; Shimizu, Soji; Shin, Ji Young; Kowalczyk, Tim; Irle, Stephan; Kim, Dongho; Shinokubo, Hiroshi.

:: Nature communications, 巻 7, 13620, 30.11.2016.

研究成果: ジャーナルへの寄稿記事

Nozawa, R, Tanaka, H, Cha, WY, Hong, Y, Hisaki, I, Shimizu, S, Shin, JY, Kowalczyk, T, Irle, S, Kim, D & Shinokubo, H 2016, 'Stacked antiaromatic porphyrins', Nature communications, 巻. 7, 13620. https://doi.org/10.1038/ncomms13620
Nozawa R, Tanaka H, Cha WY, Hong Y, Hisaki I, Shimizu S その他. Stacked antiaromatic porphyrins. Nature communications. 2016 11 30;7. 13620. https://doi.org/10.1038/ncomms13620
Nozawa, Ryo ; Tanaka, Hiroko ; Cha, Won Young ; Hong, Yongseok ; Hisaki, Ichiro ; Shimizu, Soji ; Shin, Ji Young ; Kowalczyk, Tim ; Irle, Stephan ; Kim, Dongho ; Shinokubo, Hiroshi. / Stacked antiaromatic porphyrins. :: Nature communications. 2016 ; 巻 7.
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