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 () and Hiroshi Shinokubo ()
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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

Nature Communications, 2016, vol. 7, issue 1, 1-7

Abstract: 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.

Date: 2016
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DOI: 10.1038/ncomms13620

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