Switching between Aromatic and Antiaromatic 1,3-Phenylene-Strapped [26]- and [28]Hexaphyrins upon Passage to the Singlet Excited State

Young Mo Sung, Juwon Oh, Woojae Kim, Hirotaka Mori, Atsuhiro Osuka, Dongho Kim

Research output: Contribution to journalArticle

35 Citations (Scopus)

Abstract

We have demonstrated aromaticity reversal in the singlet excited states of internally 1,3-phenylene-strapped [26]- and [28]hexaphyrins (P26H and P28H). P26H displays a broad and reduced singlet-excited-state absorption spectrum, whereas P28H exhibits a sharp and intense singlet-excited-state absorption spectrum; both are in contrast to the ground-state absorption spectra, strongly indicating aromaticity reversal in the singlet excited state. Furthermore, magnetic and topological indices of aromaticity such as nucleus-independent chemical shift and harmonic oscillator model of aromaticity values for P26H and P28H also suggest that their singlet excited states become antiaromatic and aromatic, respectively.

Original languageEnglish
Pages (from-to)11856-11859
Number of pages4
JournalJournal of the American Chemical Society
Volume137
Issue number37
DOIs
Publication statusPublished - 2015 Sep 23

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Excited states
Absorption spectra
Chemical shift
Ground state

All Science Journal Classification (ASJC) codes

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

Cite this

Sung, Young Mo ; Oh, Juwon ; Kim, Woojae ; Mori, Hirotaka ; Osuka, Atsuhiro ; Kim, Dongho. / Switching between Aromatic and Antiaromatic 1,3-Phenylene-Strapped [26]- and [28]Hexaphyrins upon Passage to the Singlet Excited State. In: Journal of the American Chemical Society. 2015 ; Vol. 137, No. 37. pp. 11856-11859.
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abstract = "We have demonstrated aromaticity reversal in the singlet excited states of internally 1,3-phenylene-strapped [26]- and [28]hexaphyrins (P26H and P28H). P26H displays a broad and reduced singlet-excited-state absorption spectrum, whereas P28H exhibits a sharp and intense singlet-excited-state absorption spectrum; both are in contrast to the ground-state absorption spectra, strongly indicating aromaticity reversal in the singlet excited state. Furthermore, magnetic and topological indices of aromaticity such as nucleus-independent chemical shift and harmonic oscillator model of aromaticity values for P26H and P28H also suggest that their singlet excited states become antiaromatic and aromatic, respectively.",
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Switching between Aromatic and Antiaromatic 1,3-Phenylene-Strapped [26]- and [28]Hexaphyrins upon Passage to the Singlet Excited State. / Sung, Young Mo; Oh, Juwon; Kim, Woojae; Mori, Hirotaka; Osuka, Atsuhiro; Kim, Dongho.

In: Journal of the American Chemical Society, Vol. 137, No. 37, 23.09.2015, p. 11856-11859.

Research output: Contribution to journalArticle

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AU - Osuka, Atsuhiro

AU - Kim, Dongho

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AB - We have demonstrated aromaticity reversal in the singlet excited states of internally 1,3-phenylene-strapped [26]- and [28]hexaphyrins (P26H and P28H). P26H displays a broad and reduced singlet-excited-state absorption spectrum, whereas P28H exhibits a sharp and intense singlet-excited-state absorption spectrum; both are in contrast to the ground-state absorption spectra, strongly indicating aromaticity reversal in the singlet excited state. Furthermore, magnetic and topological indices of aromaticity such as nucleus-independent chemical shift and harmonic oscillator model of aromaticity values for P26H and P28H also suggest that their singlet excited states become antiaromatic and aromatic, respectively.

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