TY - JOUR
T1 - Switching between Aromatic and Antiaromatic 1,3-Phenylene-Strapped [26]- and [28]Hexaphyrins upon Passage to the Singlet Excited State
AU - Sung, Young Mo
AU - Oh, Juwon
AU - Kim, Woojae
AU - Mori, Hirotaka
AU - Osuka, Atsuhiro
AU - Kim, Dongho
N1 - Publisher Copyright:
© 2015 American Chemical Society.
Copyright:
Copyright 2015 Elsevier B.V., All rights reserved.
PY - 2015/9/23
Y1 - 2015/9/23
N2 - 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.
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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U2 - 10.1021/jacs.5b04047
DO - 10.1021/jacs.5b04047
M3 - Article
AN - SCOPUS:84942274871
VL - 137
SP - 11856
EP - 11859
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 37
ER -