5,20-Bis(ethoxycarbonyl)-Substituted Antiaromatic [28]Hexaphyrin and Its Bis-NiII and Bis-CuII Complexes

Chemistry, an Asian Journal
Akito NakaiAtsuhiro Osuka

Abstract

5,20-Bis(ethoxycarbonyl)-[28]hexaphyrin was synthesized by acid catalyzed cross-condensation of meso-diaryl-substituted tripyrrane and ethyl 2-oxoacetate followed by subsequent oxidation. This hexaphyrin was found to be a stable 28π-antiaromatic compound with a dumbbell-like conformation. Upon oxidization with PbO2 , this [28]hexaphyrin was converted into an aromatic [26]hexaphyrin with a rectangular shape bearing two ester groups at the edge side. The [28]hexaphyrin can incorporate two NiII or CuII metals by using the ester carbonyl groups and three pyrrolic nitrogen atoms to give bis-NiII and bis-CuII complexes with essentially the same dumbbell-like structure. The antiaromatic properties of the [28]hexaphyrin and its metal complexes have been well characterized.

References

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Dec 15, 2018·Chemistry, an Asian Journal·Akito NakaiAtsuhiro Osuka

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Citations

Aug 6, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Susana M M LopesTeresa M V D Pinho E Melo
Aug 10, 2019·Nature Communications·Ryo NozawaHiroshi Shinokubo

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