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Protonation-coupled redox reactions in planar antiaromatic meso-pentafluorophenyl-substituted o-phenylene-bridged annulated rosarins

Authors
Ishida, MKim, SJPreihs, COhkubo, KLim, JMLee, BSPark, JSLynch, VMRoznyatovskiy, VVSarma, TPanda, PKLee, CHFukuzumi, SKim, DSessler, JL
Issue Date
Jan-2013
Publisher
NATURE PUBLISHING GROUP
Citation
NATURE CHEMISTRY, v.5, no.1, pp 15 - 20
Pages
6
Journal Title
NATURE CHEMISTRY
Volume
5
Number
1
Start Page
15
End Page
20
URI
https://scholarworks.sookmyung.ac.kr/handle/2020.sw.sookmyung/147512
DOI
10.1038/NCHEM.1501
ISSN
1755-4330
1755-4349
Abstract
Proton-coupled electron transfer (PCET) processes are among the most important phenomena that control a variety of chemical and biological transformations. Although extensively studied in a variety of natural systems and discrete metal complexes, PCET mechanisms are less well codified in the case of purely organic compounds. Here we report that a planar beta,beta'-phenylene-bridged hexaphyrin (1.0.1.0.1.0), a 24 pi-electron antiaromatic species termed rosarin, displays unique redox reactivity on protonation. Specifically, treatment with acid (for example, HI) yields a 26 pi-electron aromatic triprotonated monocationic species that is produced spontaneously via an intermediate-but stable-25 pi-electron non-aromatic triprotonated monoradical dication. This latter species is also produced on treatment of the original 24 pi-electron antiaromatic starting material with HCl or HBr. The stepwise nature of the proton-coupled reduction observed in the planar rosarin stands in marked contrast to that seen for non-annulated rosarins and other ostensibly antiaromatic expanded porphyrinoids.
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