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

Journal of the American Chemical Society
Young Mo SungDongho Kim

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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Citations

Dec 15, 2016·Journal of the American Chemical Society·Conerd K FredericksonMichael M Haley
Nov 24, 2017·Nature Chemistry·Won-Young ChaDongho Kim
Oct 29, 2015·Chemistry, an Asian Journal·Hongchao SunJun Zhu
Oct 3, 2018·Chemistry : a European Journal·Peter B KaradakovDavid L Cooper
Oct 7, 2016·Nature Communications·Raffaello PapadakisHenrik Ottosson
Oct 17, 2018·Angewandte Chemie·Takanori SoyaAtsuhiro Osuka
Mar 10, 2019·Chemistry : a European Journal·Takanori Soya, Atsuhiro Osuka
Jul 7, 2017·Chemistry : a European Journal·Rabia AyubHenrik Ottosson
Aug 29, 2020·Chemistry, an Asian Journal·Yuanyuan HuangJun Zhu
Jan 4, 2018·Chemical Communications : Chem Comm·Michał J Białek, Lechosław Latos-Grażyński
Jul 5, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ji-Young ShinHiroshi Shinokubo
Nov 1, 2018·ChemPlusChem·Bo DurbeejBaswanth Oruganti
Jan 17, 2020·ChemPlusChem·Bulti Abdisa KerayuChen-Hsiung Hung
Oct 19, 2017·Journal of the American Chemical Society·Masaki HadaR J Dwayne Miller
Aug 26, 2017·Organic Letters·Baswanth OrugantiBo Durbeej
Jul 16, 2020·Journal of the American Chemical Society·Baswanth OrugantiBo Durbeej
Mar 20, 2019·Journal of the American Chemical Society·Ting ShenJun Zhu
Jan 2, 2018·Journal of the American Chemical Society·Thijs StuyverMercedes Alonso
May 10, 2018·The Journal of Physical Chemistry Letters·Fumitoshi EmaYasuhiro Kobori
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