Möbius aromaticity in N-fused [24]pentaphyrin upon Rh(I) metalation

Kang Park Jong, Seok Yoon Zin, Min Chul Yoon, Suk Kim Kil, Shigeki Mori, Ji Young Shin, Atsuhiro Osuka, Dongho Kim

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

N-fused pentaphyrins (NFP5), stable forms of meso-aryl pentaphyrins, are interesting platforms to realize Hückel aromaticity, nonaromaticity, and Möbius aromaticity depending upon the number of π-electrons, meso-substituent, and metalation. Remarkably, Rh(I) complex of pentakis(pentafluorophenyl) substituted [24]NFP5 has been characterized as a Möbius aromatic macrocycle by the crystal structure, 1H NMR spectrum, NICS calculation, and two-photon absorption (TPA) cross section. This system is, to the best of our knowledge, the smallest Möbius aromatic molecule with a distinct diatropic ring current characterized so far. This work demonstrates the great potential of our synthetic strategy toward Möbius aromatic molecules as well as the possible use of TPA value as a quantitative measure of aromaticity.

Original languageEnglish
Pages (from-to)1824-1825
Number of pages2
JournalJournal of the American Chemical Society
Volume130
Issue number6
DOIs
Publication statusPublished - 2008 Feb 13

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Photons
Molecules
Crystal structure
Nuclear magnetic resonance
Electrons
Proton Magnetic Resonance Spectroscopy

All Science Journal Classification (ASJC) codes

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

Cite this

Jong, K. P., Zin, S. Y., Yoon, M. C., Kil, S. K., Mori, S., Shin, J. Y., ... Kim, D. (2008). Möbius aromaticity in N-fused [24]pentaphyrin upon Rh(I) metalation. Journal of the American Chemical Society, 130(6), 1824-1825. https://doi.org/10.1021/ja7100483
Jong, Kang Park ; Zin, Seok Yoon ; Yoon, Min Chul ; Kil, Suk Kim ; Mori, Shigeki ; Shin, Ji Young ; Osuka, Atsuhiro ; Kim, Dongho. / Möbius aromaticity in N-fused [24]pentaphyrin upon Rh(I) metalation. In: Journal of the American Chemical Society. 2008 ; Vol. 130, No. 6. pp. 1824-1825.
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abstract = "N-fused pentaphyrins (NFP5), stable forms of meso-aryl pentaphyrins, are interesting platforms to realize H{\"u}ckel aromaticity, nonaromaticity, and M{\"o}bius aromaticity depending upon the number of π-electrons, meso-substituent, and metalation. Remarkably, Rh(I) complex of pentakis(pentafluorophenyl) substituted [24]NFP5 has been characterized as a M{\"o}bius aromatic macrocycle by the crystal structure, 1H NMR spectrum, NICS calculation, and two-photon absorption (TPA) cross section. This system is, to the best of our knowledge, the smallest M{\"o}bius aromatic molecule with a distinct diatropic ring current characterized so far. This work demonstrates the great potential of our synthetic strategy toward M{\"o}bius aromatic molecules as well as the possible use of TPA value as a quantitative measure of aromaticity.",
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Jong, KP, Zin, SY, Yoon, MC, Kil, SK, Mori, S, Shin, JY, Osuka, A & Kim, D 2008, 'Möbius aromaticity in N-fused [24]pentaphyrin upon Rh(I) metalation', Journal of the American Chemical Society, vol. 130, no. 6, pp. 1824-1825. https://doi.org/10.1021/ja7100483

Möbius aromaticity in N-fused [24]pentaphyrin upon Rh(I) metalation. / Jong, Kang Park; Zin, Seok Yoon; Yoon, Min Chul; Kil, Suk Kim; Mori, Shigeki; Shin, Ji Young; Osuka, Atsuhiro; Kim, Dongho.

In: Journal of the American Chemical Society, Vol. 130, No. 6, 13.02.2008, p. 1824-1825.

Research output: Contribution to journalArticle

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AU - Jong, Kang Park

AU - Zin, Seok Yoon

AU - Yoon, Min Chul

AU - Kil, Suk Kim

AU - Mori, Shigeki

AU - Shin, Ji Young

AU - Osuka, Atsuhiro

AU - Kim, Dongho

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AB - N-fused pentaphyrins (NFP5), stable forms of meso-aryl pentaphyrins, are interesting platforms to realize Hückel aromaticity, nonaromaticity, and Möbius aromaticity depending upon the number of π-electrons, meso-substituent, and metalation. Remarkably, Rh(I) complex of pentakis(pentafluorophenyl) substituted [24]NFP5 has been characterized as a Möbius aromatic macrocycle by the crystal structure, 1H NMR spectrum, NICS calculation, and two-photon absorption (TPA) cross section. This system is, to the best of our knowledge, the smallest Möbius aromatic molecule with a distinct diatropic ring current characterized so far. This work demonstrates the great potential of our synthetic strategy toward Möbius aromatic molecules as well as the possible use of TPA value as a quantitative measure of aromaticity.

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