Facile formation of a benzopyrane-fused [28]hexaphyrin that exhibits distinct Möbius aromaticity

Sumito Tokuji, Jae Yoon Shin, Suk Kim Kil, Min Lim Jong, Katsuyuki Youfu, Shohei Saito, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

70 Citations (Scopus)

Abstract

(Chemical Equation Presented) A benzopyrane-fused [28]hexaphyrin, 2, was prepared by simple heating of [26]hexaphyrin 1 in acetic acid. Fused [28]hexaphyrin 2 features a molecular twist, a distinct diatropic ring current, a large HOMA value, a large negative NICS value, and a large two-photon absorption (TPA) cross section even at room temperature, all of which support the M bius aromaticity of 2. To the best of our knowledge, 2 is the first macrocycle that acquires distinct M bius aromaticity without any assistance from metal coordination, temperature control, or protonation.

Original languageEnglish
Pages (from-to)7240-7241
Number of pages2
JournalJournal of the American Chemical Society
Volume131
Issue number21
DOIs
Publication statusPublished - 2009 Jun 3

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Protonation
Temperature control
Acetic acid
Acetic Acid
Photons
Metals
Heating
Temperature

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Tokuji, S., Shin, J. Y., Kil, S. K., Jong, M. L., Youfu, K., Saito, S., ... Osuka, A. (2009). Facile formation of a benzopyrane-fused [28]hexaphyrin that exhibits distinct Möbius aromaticity. Journal of the American Chemical Society, 131(21), 7240-7241. https://doi.org/10.1021/ja902836x
Tokuji, Sumito ; Shin, Jae Yoon ; Kil, Suk Kim ; Jong, Min Lim ; Youfu, Katsuyuki ; Saito, Shohei ; Kim, Dongho ; Osuka, Atsuhiro. / Facile formation of a benzopyrane-fused [28]hexaphyrin that exhibits distinct Möbius aromaticity. In: Journal of the American Chemical Society. 2009 ; Vol. 131, No. 21. pp. 7240-7241.
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Facile formation of a benzopyrane-fused [28]hexaphyrin that exhibits distinct Möbius aromaticity. / Tokuji, Sumito; Shin, Jae Yoon; Kil, Suk Kim; Jong, Min Lim; Youfu, Katsuyuki; Saito, Shohei; Kim, Dongho; Osuka, Atsuhiro.

In: Journal of the American Chemical Society, Vol. 131, No. 21, 03.06.2009, p. 7240-7241.

Research output: Contribution to journalArticle

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T1 - Facile formation of a benzopyrane-fused [28]hexaphyrin that exhibits distinct Möbius aromaticity

AU - Tokuji, Sumito

AU - Shin, Jae Yoon

AU - Kil, Suk Kim

AU - Jong, Min Lim

AU - Youfu, Katsuyuki

AU - Saito, Shohei

AU - Kim, Dongho

AU - Osuka, Atsuhiro

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AB - (Chemical Equation Presented) A benzopyrane-fused [28]hexaphyrin, 2, was prepared by simple heating of [26]hexaphyrin 1 in acetic acid. Fused [28]hexaphyrin 2 features a molecular twist, a distinct diatropic ring current, a large HOMA value, a large negative NICS value, and a large two-photon absorption (TPA) cross section even at room temperature, all of which support the M bius aromaticity of 2. To the best of our knowledge, 2 is the first macrocycle that acquires distinct M bius aromaticity without any assistance from metal coordination, temperature control, or protonation.

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